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1
GENERAL ORGANIC CHEMISTRY
Level - 1
1.
How many 2º Hydrogen atoms are present in the given following compound ?
Cl
(a) 2
2.
(b) 5
(c) 7
(d) 8
Identify which functional group is Not present in the given following
compound?
O
O
NH
(a) Ketone
3.
O
(b) Ester
O
(c) Amide
(d) Ether
Correct energy profile for amine inversion and hybridization of nitrogen in transition state
is:
N
D
H
H
T
T
D
N
(A)
(B)
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sp3
sp3
(a)
(B)
(b)
(A)
(B)
(A)
sp2
sp2
(c)
(d)
(A)
(B)
(A)
(B)
4.
(i)
(ii)
(iii)
Correct order of the heats of combustion of above compounds is:
(a) (i) > (ii) > (iii) (b) (i) > (iii) > (ii) (c) (ii) > (i) > (iii)
5.
(d) (ii) > (iii) > (i)
Which of the following is not a resonance structure of the others ?
-
O
O
-
(a)
(b)
O
O
-
(c)
(d)
-
6.
Rank the hydrogen atoms (H a , H b , H c ) present in the following molecule in decreasing order of
their acidic strength.
Ha
O
O
H2C
Hb H H H
c
(a) a > b > c
(c) b > c > a
CH3
(b) b > a > c
(d) c > b > a
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7.
O
||
CH 3 — C — O — CH 3 ;
a
b
The correct relation between the bond lengths a and b is:
(a) a = b
(b) b > a
(c) b < a
(d) Impossible to predict
8.
The number of sp 2 - sp 2 sigma bonds in the compound given below is :
(a) 1
9.
(b) 3
(c) 4
O
(a) 2
10.
(d) 5
The total number of lone pair of electrons in the given molecule is :
N—H
(b) 3
(c) 4
(d) 5
Which of the following rings is highly strained ?
O
O
O
(a)
O
(b)
g-lactone
d-lactone
O
O
O
(c)
11.
d-lactam
The functional groups present in Cortisone are :
O
HOH2C
CH3
OCH3
Cortisone
O
(a) ether, alkene, alcohol
(c) alcohol, ketone, amine
12.
N –H
(d)
b-lactone
(b) alcohol, ketone, alkene, ether
(d) ether, amine, ketone
Select the acid with the highest K a (i . e. , lowest pK a ).
O
O
(a) H3C
OH
Cl
(b) Cl H
OH
O
O
OH
(c)
I
OH
(d) Cl
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13.
Most stable carbocation among the following is :
CH3
(a)
(b)
CH2
(c)
(d)
Å
CH 3
14.
Arrange the following in increasing order of their pK a values.
O
O
||
||
(z) CH 3 — OH
(y) CH 3 — C — O — H
(x) CH 3 — S — O — H
||
O
(a) y < x < z
(b) x < y < z
(c) y < z < x
(d) x < z < y
15.
Which is the major product of the following reaction ?
H
N
HCl
1 mole
¾¾¾®
Product
|
N
H
H
H
Cl–
H
N
(a)
N
H
(b)
H
Cl
H
H
|
N
H
N
(c)
16.
Cl–
N
|
|
N
(d)
N
|
N
Cl
H
H
In the given pair identify most acidic compound in (A) and (B). Most basic in (C) and (D).
CO2H
CO2H
CO2H
CH3
(A)
CO2H
CH3
(B)
(I)
NH2
(I)
(II)
NH2
NH2
(II)
NH2
CH3
CH3
(C)
(D)
(I)
(I)
(II)
(a) A - I, B - II, C - I, D - II
(c) A - II, B - II, C - II, D - II
(II)
(b) A - II, B - I, C - I, D - II
(d) A - I, B - II, C - I, D - I
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17.
Several factors (steric, electronic, orbital interactions etc.) can affect the inversion barrier of
an amine. In the given pair which data is correctly placed ?
i – Pr
Me
(a)
Me
|
|
N
N
Me
vs
i – Pr
Me
+
DG = 7.9 kcal/mol DG = 0.2 kcal/mol
vs
N
N
Me
Me
DG = 20.5 kcal/mol DG = 7.0 kcal/mol
Me
Cl
|
|
vs
N
N
Me
Me
(c)
Cl
Cl
(b)
+
+
DG = 7.9 kcal/mol
+
+
DG = 22.9 kcal/mol
(d) All of these
18.
Select the response that correctly identifies the number of carbon atoms of each type of
hybridization in the compound given below
H 2C == C == CH — CH == O
(a)
(c)
19.
sp 3
sp 2
sp
2
0
2
3
0
1
(b)
(d)
sp 3
sp 2
sp
1
1
3
2
0
1
Circle represents most basic atoms in these molecule. Which of the following is correct
representation ?
N–N
H
N
N
(a)
(b)
N
O
H2N
CN
(c)
20.
H2N
NH2
(d) All of these
Circle represent most acidic hydrogens in these molecules. Which of the following is correct
representation ?
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O
OH
MeO2C
OH
(a)
HO
(b)
CF3
CO2H
S
(c)
21.
(d) All of these
F
Arrange the following in decreasing order of their acidic strengths.
Å
O
|
Å
N
|
H
H
H
CH3
(B)
(A)
N
|
OH
(C)
(D)
(a) A > C > B > D
(b) A > D > B > C
(c) A > D > C > B
Cyclopropane
Cyclobutane
Cyclopentane
(I)
(II)
(III)
(d) D > A > C > B
22.
The correct order of heats of combustion of above compounds is :
(a) I > II > III
(b) II > I > III
(c) III > II > I
23.
(A)
(B)
(C)
Compare carbon-carbon bond rotation across A, B, and C
(a) A > B > C
(b) A > C > B
(c) B > A > C
24.
(d) III > I > II
(d) B > C > A
Which of the following acids would have a STRONGER CONJUGATE BASE ?
(A)
H2S
vs
1
H2O
2
O
O
NH
NH
(B)
3
(C)
O
4
CH 3C ºº CH vs CH 3CH == CH 2
5
(a) 2, 4, 6
vs
(b) 1, 3, 5
6
(c) 2, 3, 5
(d) 1, 3, 6
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KH
25.
; Major products of the reaction is (are):
¾¾
¾® A
-H 2
*
14
(C = C )
¯
H 2O
Major
Product
(a)
26.
(b)
(c)
(d) both (b)& (c)
Which of the following compound is most stable ?
C8H17
C9H19
(a)
(b)
AcO
AcO
C9H19
C8H17
(c)
(d)
AcO
27.
AcO
Selected bond angles for six hydrocarbons are shown below. Arrange these hydrocarbons
according to their pK a values, from the lowest to the highest.
H
128º
H
109.5º
H
H H
H
115º
H
H
H 108º
H
H
H
117º
(II)
(I)
H
H
H
H
120º
(VI)
(V)
(a) V < I < VI < II < III < IV
(c) II < IV < I < VI < V < III
28.
(IV)
(III)
180º
(b) IV < I < II < III < V < VI
(d) I < V < IV < III < II < VI
Which statement about the following equilibrium is true ?
OH + K+OH ¯
O¯ K+ + H2O
t-butoxide
pKa
= 15.7
pKa
= 18
(a) The equilibrium favours the products
(b) t-Butoxide is the dominant anionic species in the equilibrium
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(c) Water is the weaker acid
(d) t-Butoxide is stabilized by resonance
29.
Consider the following reaction involving two acids shown below : formic acid and HF.
O
O
K +F - + H
O-K+
H
OH
+
pKa = 3.8
Which of the following statements about this reaction are true ?
(A) Formic acid is the strongest Bronsted acid in the reaction
(B) HF is the strongest Bronsted acid in the reaction
(C) KF is the strongest Bronsted base in the reaction
(D) KO2CH is the strongest Bronsted base in the reaction
(E) The equilibrium favours the reactants
(F) The equilibrium favours the products
(G) Formic acid has a weaker conjugate base
(H) HF has a weaker conjugate base
(a) A, D and F
(b) B, D, and H
(c) A, C, and H
30.
(b)
(c)
(a)
CH2Cl
(d)
(c)
HN
CH3
(d)
H3C
H3C
C(CH3)3
NH
CH3
CH3
(b)
H3C
H3C
C(CH3)3
C(CH3)3
C(CH3)3
Rank the following substances in order of decreasing heat of combustion (maximum ®
minimum).
1
2
(a) 1 > 2 > 4 > 3
(c) 2 > 4 > 1 > 3
CH3
CH3
CH3
33.
ClCH2
ClCH2
CH2Cl
CN
HO
NC
Which one of the following has the smallest heat of combustion ?
CH3
32.
(d) B, D, E and H
Which one of the following compounds has non zero dipole moment?
OH
CN
(a)
31.
HF
pK a = 3.2
CH3
4
3
CH3
(b) 3 > 4 > 2 > 1
(d) 1 > 3 > 2 > 4
Which of the following has lowest pK a value ?
CH
(a)
(b)
CH
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(c)
34.
(d)
Arrange the following (w, x, y, z) in decreasing order of their boiling points:
OH
(w)
O
N
|
CH3
(x)
(y)
(a) w > x > z > y
(c) w > z > y > x
35.
(z)
(b) w > x > y > z
(d) w > z > x > y
Arrange the following in increasing order of their acidic strength.
O
O
O
(I)
(II)
O
(III)
O
O
OCH3
(IV)
O
(b) II < I < IV < III
(d) II < III < I < IV
O
(a) III < I < IV < II
(c) I < III < IV < II
36.
N
|
H
O
How many degrees of unsaturation are there the following compound ?
OH
O
OH
(a) 6
37.
(b) 7
(c) 10
(d) 11
The heat of hydrogenation for 3-methylbutene and 2-pentene are –30 kcal/mol and –28
kcal/mol respectively. The heats of combustion of 2-methylbutane and pentane are – 784
kcal/mol and –782 kcal/mol respectively. All the values are given under standard
conditions. Taking into account that combustion of both alkanes give the same products,
what is DH (in kcal/mol) for the following reaction under same conditions ?
(a) 0
(b) – 4
(c) – 2
(d) 2
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38.
Which of the following s-bonds participate in hyperconjugation ?
V
I
H
CH3
H
II
IV
H
III
(a) I and II
(b) I and V
(c) II and V
(d) III and IV
OH (y)
39.
HO
(w)
HO
(z)
OH
(x)
Decreasing order of acidic strength of different (–OH) groups is :
(a) w > x > y > z
(b) w > z > x > y
(c) z > w > x > y
(d) z > x > w > y
40.
Arrange the following alcohols in decreasing order of the ease of ionization under acidic
conditions.
O
(a) I > III > II
41.
OH
OH
OH
(I)
(II)
(III)
(b) I > II > III
(c) II > III > I
(d) II > I > III
Among the isomeric amines select the one with the lowest boiling point.
H
|
CH3
N
|
N
(a)
(b)
(d)
NHCH (c)
NH2
3
CH3
42.
Which one of the compounds shown below, is not an isomer of the others ?
(a)
(b)
(c)
(d)
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43.
Arrange the anions (p) CH 3 , (q) NH 2 , (r) OH - , (s) F - , in decreasing order of their basic
strength.
(a) p > q > r > s
(b) q > p > r > s
(c) r > q > p > s
(d) r > p > q > s
44.
One among the following compounds will not give effervescence with sodium carbonate:
OH
SO3H
NO2
NO2
(a) C 6H 5CO 2H
45.
46.
(c) C 6H 5OH
The carboxylic acid which has maximum solubility in water is:
(a) phthalic acid
(b) succinic acid
(c) malonic acid
(d)
NO2
(d) salicylic acid
Among the following compounds, the most basic compound is :
(a)
(b)
N
H
47.
(b)
x H
(c)
N
H
(d)
O
H
z
N
H
y
H
H
Arrange the (C – H) bonds x , y and z in decreasing order of their bond dissociation energies
in homolysis.
(a) y > x > z
(b) z > x > y
(c) z > y > x
(d) y > z > x
48.
23 g of sodium will react with methyl alcohol to give :
(a) one mole of oxygen
(b) 22.4 dm 3 of hydrogen gas at NTP
(c) 1 mole of H 2
(d) 11.2 L of hydrogen gas at NTP
49.
Which of the following is most polar?
Q
(a)
(b)
(c)
(d)
Q
50.
N–H;
NH ;
N;
O
(x)
(y)
(z)
The correct order of decreasing basic strengths of x, y and z is :
(a) x > y > z
(b) x > z > y
(c) y > x > z
(d) y > z > x
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51.
Which of the following is the strongest Bronsted acid ?
NH2
(a)
52.
53.
OH
NH2
(b)
OH
(c)
(d)
Which of the following is the strongest Bronsted base ?
H
NH2
H
N
N
(a)
(b)
(c)
H
H
H
N
(d)
Which of the following is polar aprotic solvent ?
(a) DMSO
(b) Crown ether
(c) DMG
(d) All of these
54.
Some pairs of acids are given below. Select the pair in which second acid is stronger than first
(a) CH 3CO 2H and CH 2FCO 2H
(b) CH 2FCO 2 H and CH 2ClCO 2H
(c) CH 2ClCO 2H and CH 2BrCO 2H
(d) CH 3CH 2CHFCO 2H and CH 3CHFCH 2CO 2H
55.
H — C ºº C — C ºº C — CH 3 ;
b
a
Compare the bond lengths a and b:
(a) a = b
(b) a > b
56.
(c) b > a
(d) a >>> b
Which (isomeric) amine has lowest boiling point ?
(a) 1º amine
(b) 2º amine
(c) 3º amine
(d) cannot predict
Cl
2SbCl
5
¾¾¾
¾
® P ; P will be :
57.
Cl
(a)
(c)
58.
2–
(b)
2+
2SbCl Q
6
(d) mixture of (a) and (b)
Which of the following substances is not an isomer of 3-ethyl 2-methyl pentane ?
(a)
(b)
(c)
(d) All are isomers
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59.
Which of the following is an isomer of compound 1 ?
O
||
CH 3CH 2CHO CH 3 — C — CH 3 CH 3 — CH == CH — OH CH2 — CH — CH3
(2)
( 3)
(1)
O
(4)
(a) 2
(b) 4
(c) 2 and 3
(d) all are isomers
Br
AgNO
3
¾¾¾®
(A) ;
60.
Which statement is incorrect in respect of the above reaction ?
(a) Product is aromatic
(b) Product has high dipole moment
(c) Product has less resonance energy
(d) Product is soluble in polar solvent
61.
Some pairs of ions are given below. In which pair, first ion is more stable than second?
Å
Å
(a) CH 3 — C H — CH 3 and CH 3 — C H — OCH 3
Å
Å
(b) CH 3 — CH 2 — C H — CH 3 and CH 2 == CH — CH 2 — C H 2
CH2
CH2
and
(c)
CH3
CH
CH3
(d)
CH2
62.
C
CH3
and
CH3
N
CH3
CH3
C
CH3
Among the given pairs in which pair, first compound has higher boiling point than second ?
(a) CH 3 — CH 2OCH 3 and CH 3 — C H — CH 3
|
OH
(b) CH 3 — CH 2 — CH 2 — CH 3 and CH 3 — CH 2 — CH 3
CH 2 — CH 3
|
(c) CH 3 — CH 2 — CH 2 — CH 2 — CH 3 and CH 3 — CH — CH 2 — OH
(d) CH 3 — CH 2 — CH 2 — CH 3 and CH 3 — CH 2 — CH 2 — Cl
63.
Which of the following alcohols is the least soluble in water ?
(a) Ethanol
(b) 1-Propanol
(c) 1-Butanol
(d) 1-Pentanol
64.
Which of the following alcohols is expected to have a lowest pK a value ?
(a) Ethanol
(b) 1-propanol
(c) 2, 2, 2-trifluorethanol
(d) 2-chloroethanol
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65.
66.
Which of the following alkenes is the most stable ?
(a)
(b)
(c)
(d)
Bond X is made by the overlap of which type of hybridized orbitals ?
X
3
67.
2
(a) sp and sp
(b) sp and sp
(c) sp 2 and sp 3
Increasing order of acidic strength of given compounds is :
OH
H3C
H3CO
NC
(II)
(III)
(a) III < I < IV < II
(c) I < III < IV < II
69.
(IV)
(b) II < I < IV < III
(d) I < III < II < IV
COOH + NaHCO3 ¾¾® CO2 +
(a) CO 2
OH
OH
OH
(I)
68.
(d) none of these
(b)
COONa, C is with the product :
COONa (c) both
(d) none of these
Rank in the order of increasing acidity.
(I)
OH
(II)
(III)
NH2
(a) III < I < II
(c) III < II < I
OH
(b) I < III < II
(d) II < I < III
70.
Which compound has the highest value of pK a ?
(a) Cl — CH 2 — CH 2 — COOH
(b) CH 3 — CH 2 — COOH
Cl
|
(c) CH 3 — C H — COOH
(d) CH 3 — C — COOH
|
|
Cl
Cl
71.
Consider the hydrogen atoms attached to three different carbon atoms (labeled 1, 2 & 3).
Rank the attached hydrogen atoms in order from most acidic to least acidic.
O
O
3
O
(a) 2 > 1 > 3
2
1
(b) 1 > 2 > 3
(c) 2 > 3 > 1
(d) 3 > 2 > 1
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72.
Decreasing order of acidic strengths of following compounds is :
H
(x)
(y)
(a) x > y > z
73.
(z)
(b) y > x > z
(c) z > y > x
OH
OH
&
(c)
CH3
Which of the underlined atoms in the molecules shown below have
sp-hybridization ?
(u) CH 2CHCH 3
(v) CH 2 CCHCl
(w) CH 3 CH 2+
(x) H — C ºº C — H (y) CH 3 CN
(a) x and z
(c) u, w and x
76.
OH
&
(d)
CH3 — C == O
75.
(d) z > x > y
Among the given pairs, in which pair second compound is more acidic than first ?
O
O
||
||
(a) BrCH 2NO 2 and CH 3CH 3
(b) CH 3 — C CH 2CN and CH 3 — C — CH 3
OH
74.
CN
(z) (CH 3 ) 2 CNNH 2
(b) x, y, and z
(d) v, x and y
Which of the following, is the product of the reaction between AlCl 3 and CH 3OCH 3 ?
Cl
Cl
CH3
CH3
|
|
Cl
—
Al
—
O
Cl
—
Al
—
O
(a)
(b)
CH3
|
CH3
|
Cl
Cl
Cl
Cl
CH3
|
|
Cl
—
Al
—
O
Cl
—
Al
— CH3OCH3
(c)
(d)
CH3
|
|
Cl
Cl
Which of the following compounds contain at least one secondary alcohol ?
H
OH
HO
H
O
OH
HO
(I)
(a) I, II, IV, VI
CH3
OH
HO
(II)
H
(III)
(b) I, III
OH
OH
O
(IV)
(c) I, II, III, V
CH3
HO
H
(V)
H
(VI)
(d) I, III, V
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77.
Which of the following has the most negative heat of hydrogenation ?
(a)
78.
(b)
(d)
Which of the following options is the correct order of relative stabilities of cations I, II and III
as written below (most stable first) ?
+
CH 3
CH2
|
+
+
(I)
(II) H 2C == CH — CH 2 — C H — CH 3
(III) H 3C — C — C H 2
|
CH 3
(a) I > II > III
79.
(c)
(b) II > III > I
(c) III > I > II
(d) I > III > II
What is the decreasing order of stability (most stable ® least stable) of the following
carbocations ?
+
+
1
+
+
+
4
3
2
(a) 3 > 2 > 1 > 4 > 5
(c) 1 » 4 > 2 » 5 > 3
5
(b) 3 > 2 > 5 > 4 > 1
(d) 3 > 1 » 4 > 2 » 5
H
80.
the hydrogen indicated by arrow will be easily removed as :
(a) H +
(b) H Q
(c) H ·
81.
Rank the bond dissociation energies of the bonds indicated with the arrows. (from smallest
to largest).
H
|
2
CH2
1
H
3
H
(a) 1 < 2 < 3
82.
(d) H -2
(b) 3 < 2 < 1
(c) 2 < 3 < 1
(d) 3 < 1 < 2
Rank the following compounds in order of decreasing acid strength (most acidic ® least
acidic) .
OH
OH
OH
OH
NO2
NO2
1
(a) 2 > 4 > 1 > 3
2
(b) 1 > 3 > 4 > 2
3
4
(c) 3 > 1 > 2 > 4
(d) 3 > 1 > 4 > 2
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83.
Rank the following compounds in order of increasing acidity (weakest acid first).
Cl
Cl
CH3
OH
H3C
OH
Cl
84.
NO2
3
2
(b) 3 < 1 < 2
(c) 1 < 2 < 3
(d) 2 < 1 < 3
Which of the following phenols has the largest pK a value (i . e. , is least acidic) ?
(a) Cl
(b)
OH
(c) H3C
85.
OH
O2N
CH3
1
(a) 2 < 3 < 1
NO2
(d) N
OH
O2N
OH
C
OH
Among the given sets, which represents the resonating structures ?
(a) H — C ºº N — O
and H — O — C ºº N
(b) H — O == C == N
and H — O — C ºº N
O
(c) H — C ºº N — O
86.
and H — C — N
(d) H — O — C ºº N
and H — N == C == O
Identify each species in the following equilibrium according to the code :
SA = stronger acid ; SB = stronger base ; WA = weaker acid ; WB = weaker base.
The pK a of (CH 3 ) 2 NH is 36 ; the pK a of CH 3OH is 15.2.
CH 3OH + (CH 3 ) 2 NH
1
(a) WA
(e) WA
1
2
2
WB
WA
1
(b) WB
+
º
CH 3 — O - + CH 3 — NH — CH 3
|
H
2
1
2
1 2
WA
(c) SA SB
(d) SB SA
87.
The hydrogen bonding is strongest in which one of the following set ?
(a) F — H - - - F
(b) O — H - - - S
(c) S — H - - - F
(d) F — H - - - O
88.
Intermolecular hydrogen bonding is strongest in :
(a) methylamine
(b) phenol
(c) formaldehyde
O
a
d O
O–H
89.
H
(d) methanol
SH
OH
OH
c
b
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18
Identify most acidic hydrogen in given compound.
(a) a
(b) b
(c) c
90.
Which of the following compounds would you expect to be strongest carbon
acid ?
O
91.
(d) d
O
O
(a)
(b)
(c) CH2(CO2Et)2
(d) CH3COCH2COOC2H5
O
5-Bromo-2-cyclopropyl cyclohex-2-enol have correct structure is:
Br
OH
(a)
(b)
HO
Br
OH
Br
(c)
(d)
OH
Br
92.
Rearrange the following in the increasing order of acidic strength.
(i) benzoic acid
(ii) p-methoxybenzoic acid
(iii) o-methyoxybenzoic acid
(a) i < ii < iii
(b) iii < i < ii
(c) ii < i < iii
(d) iii < ii < i
93.
In the following acid-base reaction, in which can backward reaction if favoured?
(a) EtO +
(b) KH + EtOH
OH
O
(c) Me3CO + H 2O
94.
95.
(d)
+ CH3OH
Which compound posses highest dipole moment ?
(a) naphthalene
(b) phenanthrene
(c) anthracene
(d) azulene
H2
¾
¾
¾®
catalyst
(E1 )
H
2
¾(E
¾¾
®
)
2
H
2
¾(E
¾¾
®
)
3
(E = activation energy)
Relation between activation energies of above reactions is :
(a) E 2 > E 1 > E 3
(b) E 3 > E 1 > E 2
(c) E 3 > E 2 > E 1
(d) E 1 > E 2 > E 3
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19
96.
Rank the following solvents in decreasing order of ability to dissolve given compound.
Solvent
Et2O
H2O
EtOH
¾®
Solute
(b) H 2O > EtOH > Et 2O
(d) Et 2O > EtOH > H 2O
(a) Et 2O > H 2O > EtOH
(c) H 2O > Et 2O > EtOH
Me2N:
:NMe2
97.
1, 8-Bis (dimethylamino)
naphthalene is after referred
so as (Proton sponge)
Its basic strength is 1010 more than 1-dimethyl amino naphthalene.
Reason for high basic strength is :
(a) resonance
(b) steric inhibitation of resonance
(c) ortho effect
(d) hyperconjugation
98.
In the given pair of compounds, in which pair second compound has higher boiling point
than first compound ?
(a)
O
OH and
O and
(b)
(c) HO — CH 2 — CH 2 — OH and CH 3 — CH 2 — CH 2 — OH
CH3
|
(d)
N
Me
NH
and
Me
Me
N
Me
N
Me
99.
Me
,
;
Me
Me
NO2
NO2
(A)
(B)
(a) (A) = 6.87D, (B) = 4.11D
(c) (A) = 4.11 D , (B) = 4.11 D
100.
Dipole moments of given compound will be :
(b) (A) = 4.11 D , (B) = 6.87 D
(d) (A) = 6.87 D, (B) = 6.87 D
Order of decreasing basic strengths of halides is :
(a) F - > Cl - > I - > Br (b) F - > Cl - > Br - > I (c) I > Br > Cl > F
(d) I - > Cl - > Br - > F -
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20
101.
Among the xylenes, which is thermodynamically most stable ?
(a)
(b)
(c)
(d) All are equally stable
102.
Heat of combustion of two isomer x and y are 17 kJ/mol and 12 kJ/mol respectively. From
this information it may be concluded that :
(a) isomer x is 5 kJ /mol more stable
(b) isomer y is 5 kJ/mol less stable
(c) isomer y has 5 kJ/mol more potential energy
(d) isomer x is 5 kJ/mol less stable
103.
Rank the following substances in decreasing order of heat of combustion (most exothermic
¾® least exothermic)
(A)
(a) B > A > C
(C)
(B)
(b) A > B > C
(c) C > A > B
(d) C > B > A
104.
(1)
(2)
(3)
(4)
Choose the statement that best describes given compounds.
(a) 1, 3, 4 represent same compound
(b) 1 and 3 are isomer of 2 and 4
(c) 1, 4 are isomer of 2 and 3
(d) All the structure represent the same compound
105.
Decreasing order of acid strengths is :
Å
Ph — OH ,
(A )
Ph — CH 2 — OH ,
( B)
(a) B > A > C > D
(c) C > A > D > B
106.
Ph — CO 2H ,
(C)
Ph — CH 2 — N H 3
(D )
(b) C > A > B > D
(d) C > B > A > D
Rank the following in decreasing order of basic strength is :
(A) CH 3 — CH 2 — C ºº C (B) CH 3 — CH 2 — S (C) CH 3 — CH 2 — CO -2
(D) CH 3 — CH 2 — O -
(a) B > A > D > C
(c) A > D > B > C
(b) D > A > B > C
(d) A > D > C > B
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107.
Among the given compound choose the two that yield same carbocation on ionization.
Br
Br
Br
(A)
(C)
(B)
(a) A, C
108.
Br
(b) B, D
Oxalic acid
pK 1
Malonic acid
pK 2
Heptanedioic acid
pK 3
(D)
(c) A, B
(d) B, C
where pK 1 , pK 2 , pK 3 are first ionization constants. Correct order is :
(a) pK 1 > pK 2 > pK 3 (b) pK 1 < pK 2 < pK 3 (c) pK 3 > pK 2 = pK 1 (d) pK 3 > pK 1 > pK 2
109.
In sets a – d, only one of the set is incorrect regarding basic strength. Select it :
NH2
(a) Ph — NH — Ph 1 < Ph — NH 2 <
(strong base)
H
|
N
(b)
N
|
<
<
N
H
NH2
NH2
NH2
N
(c)
N
>
N
H
<
(b)
(c)
1°
3°
(d)
O
3°
(b) Et 2NH > Et 3H > EtNH 2 > NH 3
2°
CH3
O
O
Correct order of basic strengths of given amines is :
(a) Me 2NH > MeNH 2 > Me 3N > NH 3 (Protic solvent)
2°
<
NO2
Dipole moment of which ketone is maximum ?
O
(a)
111.
(d)
N
|
|
H
110.
>
(Protic solvent)
1°
(c) Me 3N > Me 2NH > Me - NH 2 > NH 3 (Gas phase)
(d) All are correct
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22
NH2
CH3
112.
113.
114.
Order of basic strength Ph — NH 2 , Ph — NH — Me , Ph — N — Me,
|
(A)
(B)
Me
(C)
(D)
(a) A > B > C > D (b) B > A > C > D (c) C > B > A > D (d) C > B > D > A
Carbon-carbon double bond length will be maximum in which of the following compounds ?
(a) CH 3 — CH == CH 2
(b) CH 3 — CH == CH — CH 3
(c) CH 3 — C == C — CH 3
(d) CH 2 == CH 2
|
|
CH 3 CH 3
Which has maximum dipole moment ?
(a)
(b)
O
O
||
||
C
C
(c)
115.
(d)
(i) Et 3N
(ii)
(iii)
N
N
N
Compare the basic strengths of compounds given:
(a) (i) > (ii) > (iii)
(b) (ii) > (i) > (iii)
(c) (ii) > (iii) > (i)
(d) (iii) > (ii) > (i)
116.
For the following two reactions, which statement is true ?
E
E
reactants
reactants
products
Reaction A
(a)
(b)
(c)
(d)
products
Reaction B
Reaction A is faster and less exergonic than B
Reaction B is faster and more exergonic than A
Reaction A is faster and less endergonic than B
Reaction B is faster and more endergonic than A
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23
O
117.
a
Å
H
¾¾
¾®
b
c
d
N
|
CH3
Identify the site, where attack of H + is most favourable.
(a) a
(b) b
(c) c
118.
119.
Rank the following alkenes on order of increasing l max .
(1)
(2)
(3)
(a) 1 < 2 < 3
(b) 1 < 3 < 2
(c) 2 < 1 < 3
Which of the following cyclic amine has lowest
(a)
120.
(d) d
N – CH3 –Me (b)
N – n-Bu
DG#
(c)
(d) 2 < 3 < 1
for inversion ?
N – t-Bu
Rank in the order of increasing acidic strength:
O
O
EtO2C
CO2Et
CO2Et
(d)
N – Ph
CO2Et
O
O
CO2Et
121.
(A)
(B)
(C)
(a) A < B < C
(b) A < C < B
(c) B < A < C
(d) B < C < A
Which one of the following dienes would you expect to be the most stable ?
(a)
(b)
(c)
(d)
122.
Which metal catalyzed reaction would release the maximum amount of heat per CH2 unit ?
(a) cyclopropane + H 2 ® propane
(b) cyclobutane + H 2 ® butane
(c) cyclopentane + H 2 ® pentane
(d) cyclohexane + H 2 ® hexane
O
O
O
123.
(A)
–
(B)
(C)
–
Compare basic strengths of the above compounds:
(a) A > B > C
(b) B > A > C
(c) C > A > B
–
(d) C > B > A
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24
124.
On reaction with acid, 4-pyrone gives a very stable cationic product. Which of the following
structures shows the protonation site in that product ?
O
4-Pyrone
O
O
O
(a)
125.
H
H
Å
O
O
(c)
H
(d)
O
O
H
Which of the following is the most stabilized carbocation ?
(b)
Å
O
H
OMe
OMe
Å
(a)
Å
(c)
Å
OMe
Å
(d)
Which carbocation is the most stable ?
(a)
(b)
Å
(c)
127.
H
Å
(b)
OMe
126.
ÅO
Å
Å
(d)
Å
128.
Consider a positively charged C 2H 3 species in which the positively charged carbon is sp hybridized, the uncharged carbon is sp 2 -hybridized and an empty p-orbital is perpendicular
to the p system. What it the best description of this cation ?
(a) vinyl
(b) allenyl
(c) alkyl
(d) allyl
Which of the following reactions is not exothermic ?
(a) CH3 — Cl + CH3 — CH3
CH4 + CH3 — CH2 — Cl
¾®
(b) CH3 — Cl + (CH3)3 C — H
CH4 + (CH3)3 C — Cl
¾®
(c) CH3 — Cl + CH2 == CH — CH3 ¾®
CH4 + CH2 == CH — CH2 — Cl
(d) CH3 — Cl + CH2 == CH2
CH4 + CH2 == CHCl
¾®
129.
List the following carbocations in order of decreasing stabilization energies.
+
+
(I)
(II)
(a) II, III, I, IV
130.
(b) III, IV, II, I
+
(III)
(c) III, IV, I, II
+
(IV)
(d) I, II, IV, III
For the following two acid-base reactions, which statement is true ?
(I) CH 3CH -2 +
CH 3NH 2
(II) F -
H 2O
pK a = 15.7
+
pK a =35
CH 3CH 3 + CH 3NH pK a =50
HF
pK a =3.2
+ HO -
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131.
(a) I is favoured to the right, II is favoured to the left
(b) I is favoured to the left, II is favoured to the right
(c) I is favoured to the right, II is favoured to the right
(d) I is favoured to the left, II is favoured to the left
Rank the hydrogen atoms (H a , H b , H c ) in the following molecules according to their acidic
strengths:
Ha
Hc
Hb
(a) a > b > c
(c) b > c > a
In which of the following reactions, backward reaction is favoured ?
(a) H — C ºº C — H + Li+ –CH2CH3
H — C ºº C :Q Li+ + H3C — CH3
O
O
OH
F 3C
+ –OCH2CH3
F3C
- + HOCH2CH3
O:
:
(b)
Å
+
&& - H
CH 3CH 2SH + CH 3CH 2 O
(c) CH 3CH 2 SH 2 + CH 3CH 2OH
|
H
+
NH3
+
NH2
OH
OH2
+
+
(d)
133.
(d) a > c > b
:
132.
(b) b > a > c
Which carbocation is the most stabilized ?
Å
(a)
(b)
(c)
Å
(d)
Å
Å
Taking into account of hybridization and resonance effects, rank the following
bonds in order of decreasing bond length.
:O:
(II)
(I)
: :
:
134.
O
O
: :
(III)
(a) I > II = III
135.
(b) II > III > I
(c) I > III > II
(d) II = III = I
Which one among the following carbocations has the longest half-life ?
+
+
(a)
C
(b)
C
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26
+
136.
+
C
(c)
(d)
Rank the following alkenes in order of decreasing heats of hydrogenation (largest first)
1
(b) 2 > 4 > 3 > 1
4
(c) 1 > 3 > 4 > 2
(d) 1 > 4 > 3 > 2
Which of the following reactions is most exothermic ?
hv
+ Cl2 ¾¾
®
(a)
Cl + HCl
hv
+ Cl2 ¾¾
®
(c)
138.
3
2
(a) 2 > 3 > 4 > 1
137.
CH 3 — C — CH 3
|
CH 3
hv
+ Br2 ¾¾
®
(b)
Cl + HCl
Br + HBr
hv
+ Br2 ¾¾
®
(d)
Br + HBr
Which energy diagram best represents the given reaction ?
CH3
hn
H3C
(a)
139.
E
(b)
E
(c)
Which one of the following is most stable ?
H Br
H Br
H
H
H
H
+
(a)
(b)
H
+
H
:NH2
140.
H3C
H
CH3
E
(d)
E
Br
H Br
(c)
H
(d)
H
H
+NH
:NH2
H
H
H
H
H
H
+
H
:NH2
2
Which of the following is strongest acid ?
H
H
+
(a) H - N +- H
N –H
(b)
H
H
+
H +H
N
H
N
(c)
(d)
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141.
Compare relative stability of the following resonating structure.
O
O–
O
(i)
142.
(ii)
C
(iii)
C
N
N
N
(a) (i) > (ii) > (iii) (b) (ii) > (i) > (iii) (c) (i) > (iii) > (ii)
Compare relative stability of the following resonating structure.
O
O
(p)
(q)
CH3
(a) p > q > r
(r)
N
N
(b) q > p > r
(b)
(c) q > r > p
(d) p > r > q
(c)
(d)
Which of the following has the lowest barrier to rotation about the indicated bond ?
(a)
145.
O
Which of the following isomeric hydrocarbons is most acidic ?
(a)
144.
(d) (ii) > (iii) > (i)
C
N
143.
C
(b)
(c)
(d)
Use the following data to answer the question below.
H2
Ni
( DH = - 28.6 kcal mol -1 )
excess H2
(Ni)
( DH = - 116.2 kcal mol -1 )
Anthracene
146.
Calculate the resonance energy of anthracene:
(a) 84 kcal mol
(b) 100 kcal mol
(c) 110 kcal mol
(d) 116 kcal mol
How many double bond equivalents does a compound of molecular formula
C 6 H 12O 6 possess?
(a) 0
(b) 1
(c) 2
(d) 3
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147.
How many double bond equivalents does amoxycillin (shown below) possess ?
NH2 H
N
S
O
HO
O
amoxycillin
148.
N
CO2H
(a) 5
(b) 6
(c) 7
(d) 9
What is the oxidation state of osmium in 7B and 7C, respectively ?
O
O
O
O
Os
Os
+
O
7A
(a) 6, 8
O
O
Ha
(b) 8, 6
7B
O
O
O
7C
(c) 6, 6
(d) 8, 8
Hb
149.
N
N
| Hd |
H
He
150.
Hc
Identify most acidic hydrogen present in the above compound:
(a) a
(b) b
(c) c
Which of the following compounds has most acidic hydrogen ?
O
(a)
(b)
CH
S
CH
O
151.
S
H
|
N
(c)
O
(d)
CH
CH
N
N
|
H
H
Acetic acid, (CH3COOH), has a pK a of 4.8. Ethanol, (CH 3CH 2OH), has a pK a of 16.0. What
are the major species present, when acetic acid and ethanol are added to water and the pH is
adjusted to 7.0 ?
(a) CH 3CO 2H and CH 3CO 2OH
(b) CH 3CH 2O - and CH 3CH 2OH
(c) CH 3CO 2H and CH 3CH 2O -
152.
(d) d
(d) CH 3CO -2 and CH 3CH 2OH
O
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The most stable canonical structure of given molecule is:
Q
Q
Å
Å
O
O
(a)
(b)
O
(c)
Q
Å
O
(d)
Å
In the potential energy diagram to the right, the point X represents :
Potential energy
153.
Q
X
W
Y
Electronic Reorganization
(a) a transition state
(c) a resonance hybrid
CH3
154.
(b) a reaction intermediate
(d) a reactant
CH2
(I)
(III)
(II)
Which of the following orders is correct for heat of hydrogenation of these compounds ?
(a) I > III > II
(b) III > II > I
(c) III > I > II
(d) II > I > III
CH3
CH3
CH2
155.
(I)
CH3
CH3
(II)
CH3
(III)
Which of the following orders is correct for heat of hydrogenation of these compounds ?
(a) I > II > III
156.
CH 2 == O ¬¾®
(b) III > II > I
Å
CH 2 — O
Q
¬¾®
(c) II > III > I
Q
CH 2 — O
(d) III > I > II
Å
(I)
(II)
(III)
Which of these structures is practically not a valid canonical structure for formaldehyde ?
(a) I
(b) II
(c) III
(d) None of these
157.
CH 2 == CH — CH == CH — ÅNH 3 ;
(I)
Å
Å
CH 2 —CH ==CH —
Q
CH —
Å
NH 3
(II)
CH 2 — CH == CH — CH == NH 3
(III)
Which of these structures is not a valid canonical structure ?
(a) I
(b) II
(c) III
(d) none of these
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O
||
C
158.
¨
Q
CH2
H
OQ
|
C
Å
¨
CH2
H
(I)
Q
O?Q
|
C
CH2
H
(II)
(III)
The correct order of stability for the given canonical structures is :
(a) I > III > II
(b) III > I > II
O
O
Å
(I)
(II)
(c) II > III > I
(d) II > I > III
Å
O
Å
159.
(III)
The most stable canonical structure among the given structure is :
(a) I
(b) II
(c) III
(d) all are equally stable
160.
OCH3
(I)
(II)
OCH3
OCH3
(III)
For the given compounds the correct order of resonance energy is :
(a) III > I > II
(b) II > I > III
(c) I > II > III
(d) III > II > I
Å
161.
O–H
||
CH3 – C – N
(I)
CH3
OH
|
CH3 – C – N
Å
(II)
CH3
CH3
CH3
OH
|
Å
CH3 – C = N
(III)
The correct stability order of the given canonical structures is :
(a) I > II > III
(b) III > I > II
(c) I > III > II
CH3
CH3
(d) II > III > I
O
162.
In the above compound, how many sites are available for the attack of CH 3O - ?
163.
(a) 1
CH2 == CH2
(I)
(b) 2
CH3O – CH == CH2
(II)
(c) 3
(d) 4
CH3O – CH == CH – C – OEt
||
O
(III)
Which of the following orders of rotation barrier about the C = C bond, as indicated, is
correct ?
(a) I > II > III
(b) III > II > I
(c) III > I > II
(d) II > I > III
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164.
CH
CH2
CH
(I)
CH
(II)
CH
CH
OCH3
(III)
Which of the following orders of rotation barrier about the C == C bond, as indicated, is
correct?
(a) I > II > III
(b) III > II > I
(c) III > I > II
(d) II > I > III
165.
Which of the following compound is not resonance stabilized ?
(a)
166.
167.
s
O
(b)
O
O
Homologous compound have same:
(a) General formula
(c) Structural formula
Most acidic is:
OH
(a)
s
(c)
(d)
s
O
(b) Emperical formula
(d) Molecular formula
OH
OH
(b)
OH
(c)
(d)
NO2
CH3
NO2
168.
Which of the following substituents will decrease the acidic strength of phenol?
(a) —NO 2
(b) —CN
(c) —CH 3
(d) —CHO
169.
Which of the following structures possesses a cross-conjugated system?
(a) CH 2 == CH — CH == CH — CH 2
(b) CH 2 == CH — C == CH 2
|
CH 2CH 3
(c) CH 2 == CH — CH — CH == CH 2
(d) CH 2 == CH — C == CH 2
|
|
CH == CH 2
CH == CH2
170.
Examine the following resonating structures of formic acid for their individual stability and
then answer the question given below.
O
O–
O–
O+
+
+
–
H—C—OH¬¾®H—C== O—H¬¾®H—C—OH¬¾®H—C—OH
I
II
III
IV
Which of the following arrangements gives the correct order of decreasing stability of the
above-mentioned resonance contributors?
(a) II > I > III > IV
(b) I > II > III > IV
(c) IV > III > I > II
(d) IV > III > I > II
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171.
Which of the following is not resonating structure of each other?
(a) CH 3 — N == C == S and CH 3 — S — C ºº N
+
+
(b) CH 3 — C == O and CH 3 — C ºº O
O
O|
||
+
(c) CH 3 — C — OH and CH 3 — C == O — H
+
(d) CH 2 == CH — C ºº N and CH 2 — CH == C == N 172.
In the molecule CH 3C ºº CCH == CH 2 , the maximum number of carbon atoms
arranged linearly is:
(a) 2
(b) 3
(c) 4
(d) 5
173.
The stability order of the following carbocations is:
174.
+
+
+
I
II
III
IV
(a) II > IV > III > I
(b) IV > II > III > I
(c) II > III > I > IV
(d) I > III > II > IV
Total number of a-hydrogen in given compound is:
(a) 4
175.
+
(b) 5
In which pair second ion is more stable than first?
s
r
r
s
(i)
r
(d) 7
OH
r
r
CH3
s
(ii)
(iv)
(iii)
(a) (i) and (ii)
(c) (ii) and (iv)
176.
(c) 6
(b) (ii) and (iii)
(d) (iii) and (iv)
Which one is the most stable cation in the following ?
OH
OH
OH
(a)
r
(b)
r
(c)
OH
r
(d)
r
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The most reactive amine towards dilute hydrochloric acid is ________.
CH2NH2
CONH2
(b)
NH
(c)
(d)
:
(a)
NH2
:
177.
178.
179.
180.
N
H
How many resonance structures are there for anthracene ?
(a) 6
(b) 5
(c) 4
(d) 2
Which base is strong enough to convert (CH 3 ) 3 COH into (CH 3 ) 3 CONa in a reaction that
goes to completion ?
(a) NaNH 2
(b) CH 3CH 2Na
(c) NaOH
(d) CH 3CO 2Na
(e) More than one of the above
Based upon an understanding of product stability, predict the product formed when the
following dianion reacts with one equivalent of acid
Os
Os
Hr
OH
s
O
(a)
Os
OH
O
s
O
(b)
Os
O
(c)
(d)
O
sO
(e)
181.
Rank the following alkyl radicals in order of increasing stability (least < < < most).
Ph
1
182.
2
3
(a) 4 < 2 < 1 < 3
(b) 3 < 1 < 2 < 4
(c) 1 < 3 < 4 < 2
Among the given cations, the most stable carbonium ion is ?
(a) sec-butyl
(b) tert-butyl
(c) n-butyl
4
(d) 2 < 4 < 3 < 1
(d) None of these
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183.
184.
185.
186.
Cyclohexadiene contains ____ vinylic and _____ allylic hydrogen atoms ?
(a) 2 and 2 respectively
(b) 4 and 4 respectively
(c) 2 and 4 respectively
(d) 4 and 2 respectively
The dipole moments of halo compounds are in the order
(a) CHCl 3 > CCl 4 > CHCl 2 > cis - CHCl = CHCl
(b) cis - CHCl = CHCl > CHCl 3 > CH 2Cl > CCl 4
(c) cis - CHCl = CHCl > CH 2Cl 2 > CHCl 3 > CCl
(d) CHCl 3 > CHCl 2 > cis - CHCl = CHCl > CCl 4
The pka value in H 2O of picric acid, acetic acid and phenol are in the order :
(a) Picric acid 0 .4, acetic acid 4 .75, phenol 10 .0
(b) Acetic acid 0 .4, picric acid 4 .75, phenol 10 .0
(c) Picric acid 0 .4 phenol 4 .75, acetic acid 10 .0
(d) Phenol 0 .4, acetic acid 4 .75 picric acid 10 .0
The preferred sites of protonation in the following compounds are:
O1
CH3
NHCH3
2
NH2
N
3
(i)
187.
(a) 1 and 3
Among i-iii
4
(ii)
(b) 2 and 4
(c) 1 and 4
(d) 2 and 3
OH
OH
OH
OH
188.
189.
OH
(i)
(ii)
(iii)
the boiling point follows the order
(a) (ii) < (i) < (iii) (b) (iii) < (ii) < (i) (c) (i) < (ii) < (iii)
The number of C — C sigma bonds in the compound
O
(d) (ii) < (iii) < (i)
(a) 16
(b) 14
(b) 18
(d) 11
The correct order of dipole moment for the following molecules is
F
F
F
F
F
F
Cl
F
F
F
(I)
(a) IV > I > III > II
(II)
(b) I > IV > III > II
(III)
(IV)
(c) III > I > II > IV
(d) II > III > IV > I
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190.
Curved arrows are used in Organic Chemistry to show the movement of electrons in the
mechanism of a reaction. The correct product of the following reaction is
O
(a)
191.
O
O
O
(b)
(d)
Which of the following will form carbocation most readily ?
O
O
HClO4
(a)
Cl
OH
(c)
HClO4
(b)
O
192.
O
(c) H
HClO4
(d)
AlCl3
Observed heat of hydrogenation for cyclohexa-1,4-diene and cyclo
hexa-1,3-diene is x & y kcal/mol respectively, calculate the resonance energy of
cyclohexa-1,3-diene :
3x
2x
(b)
(a)
-y
-y
2
2
3y
2y
(c)
(d)
-x
-x
2
2
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ANSWERS – LEVEL 1
1.
(c)
2.
(d)
3.
(d)
4.
(a)
5.
(d)
6.
(d)
7.
(b)
8.
(c)
9.
(b)
10.
(c)
11.
(b)
12.
(b)
13.
(a)
14.
(b)
15.
(b)
16.
(b)
17.
(d)
18.
(c)
19.
(d)
20.
(d)
21.
(c)
22.
(c)
23.
(c)
24.
(a)
25.
(d)
26.
(d)
27.
(d)
28.
(a)
29.
(d)
30.
(a)
31.
(c)
32.
(c)
33.
(d)
34.
(d)
35.
(d)
36.
(d)
37.
(b)
38.
(b)
39.
(a)
40.
(c)
41.
(c)
42.
(d)
43.
(a)
44.
(c)
45.
(c)
46.
(d)
47.
(b)
48.
(d)
49.
(b)
50.
(b)
51.
(d)
52.
(d)
53.
(d)
54.
(a)
55.
(c)
56.
(c)
57.
(b)
58.
(b)
59.
(d)
60.
(c)
61.
(b)
62.
(b)
63.
(d)
64.
(c)
65.
(d)
66.
(c)
67.
(a)
68.
(a)
69.
(d)
70.
(b)
71.
(a)
72.
(d)
73.
(d)
74.
(d)
75.
(a)
76.
(d)
77.
(a)
78.
(a)
79.
(b)
80.
(a)
81.
(d)
82.
(d)
83.
(d)
84.
(c)
85.
(b)
86.
(a)
87.
(a)
88.
(b)
89.
(a)
90.
(d)
91.
(b)
92.
(c)
93.
(d)
94.
(d)
95.
(d)
96.
(d)
97.
(b)
98.
(d)
99.
(a)
100.
(b)
101.
(b)
102.
(d)
103.
(a)
104.
(a)
105.
(c)
106.
(c)
107.
(c)
108.
(b)
109.
(c)
110.
(c)
111.
(d)
112.
(c)
113.
(c)
114.
(c)
115.
(c)
116.
(a)
117.
(a)
118.
(d)
119.
(c)
120.
(c)
121.
(c)
122.
(a)
123.
(c)
124.
(c)
125.
(d)
126.
(b)
127.
(a)
128.
(d)
129.
(b)
130.
(a)
131.
(c)
132.
(d)
133.
(c)
134.
(d)
135.
(a)
136.
(d)
137.
(c)
138.
(d)
139.
(c)
140.
(c)
141.
(a)
142.
(d)
143.
(b)
144.
(c)
145.
(a)
146.
(b)
147.
(d)
148.
(b)
149.
(a)
150.
(b)
151.
(d)
152.
(b)
153.
(a)
154.
(a)
155.
(c)
156.
(c)
157.
(c)
158.
(b)
159.
(c)
160.
(c)
161.
(b)
162.
(c)
163.
(a)
164.
(a)
165.
(c)
166.
(a)
167.
(d)
168.
(c)
169.
(d)
170.
(b)
171.
(a)
172.
(c)
173.
(c)
174.
(c)
175.
(b)
176.
(b)
177.
(c)
178.
(c)
179.
(e)
180.
(d)
181. (c)
182.
(b)
183.
(b)
184.
(c)
185.
(a)
186.
(a)
187.
(a)
188.
(b)
189. (b)
190.
(c)
191.
(c)
192.
(b)
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37
Level - 2
1.
Rank in order of radical stability (1 = most stable).
(a)
(b)
*
2.
(c)
*
(d)
*
*
Predict the acidity order for the three phenols shown below :
Acidity order : 1 (most) to 3 (least)
OH
(a)
(b)
Me
OH
OH
O
(c)
Me
Me
||
O
Acidity order : ...........
...........
............
3. Comprehension
OH
OH
O2N
(A)
OH
NO2
(B)
(C)
NO2
NO2
CH3
OH
OH
OH
H2N
(D)
NH2
(E)
(F)
NO2
NH2
C
O
CH3
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38
A.
Which of the phenol derivatives above is the strongest acid ?
*
*
B.
*
*
Compound A
Compound D
*
*
Compound B
Compound E
Compound C
Compound F
Which of the phenol derivatives above is the weakest acid ?
*
*
C.
*
*
Compound B
Compound E
Compound C
Compound F
Which of the mono-nitrophenol derivatives above is the strongest acid ?
*
D.
*
*
Compound A
Compound D
*
Compound A
Compound D
Which of the carbon-substituted phenol derivatives above is the strongest acid ?
*
4.
*
Compound C
Compound F
The following questions refer to the twelve compounds given below. You may enter as many
as six choices in each answer box.
O
(a)
(b)
(c)
N
(d)
H3C
O — C2H5
OH
CH3
CH3
(e)
H —F
(f)
CH3
O
O
(g)
O
(h)
(i)
O—H
O
NH2
(j)
H3C
(k)
(l)
N
O
A.
Which compound may serve only as H-bond donors ?
B.
Which may serve both as H-bond donors and acceptors?
C.
Which compounds will not participate in H-bonding ?
5.
Consider the following compounds and answer A and B.
(I)
(II)
N
|
H
A.
(III)
N
|
H
(IV)
O
O
O
O
N
|
H
O
Which of the compounds is the strongest Bronsted acid ?
(a) I
(b) II
(c) III
(d) IV
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B.
Which of the compounds is the strongest Lewis base ?
(a) I
6.
(b) II
(c) III
(d) IV
Rank the non-bonding electrons indicated by the arrows in order of increasing energy.
B
C
..
N
–
A
H3C
H3C – . .
N
..
N — CH3
O
7.
In each of the following sections four nitrogen containing compounds are listed. In the box
under each formula write a number (1 to 4) indicating the order of base strength.
N—H
(a)
N — CH3
N
O2N
O
NH2
O
NH2
N—H
O2N
(b)
NH2
N—H
O
N—H
N(CH3)2
N—H
(c)
N
N—H
N — CH3
H
H3C
(d)
H3C
N—H
C ºº N
N—H
N
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8.
For the two sets of acids shown below, rank their acidity most acidic to least acidic.
Br
O
Br
O
OH
OH
(a)
O
O
OH
OH
Br
Br
(i)
(ii)
(iii)
O
O
(iv)
O
O
Br
(b)
(i)
9.
OH
OH
Br
(ii)
OH
Br
OH
Br
Br
Br
(iii)
(iv)
In each of the following sections four compounds are listed. In the box under each formula
enter a number (1 to 4) indicating the order of acid strength (1 is strongest & 4 is weakest).
(a)
(b)
CH 3CH 2CH 2CO 2H
CH 3CH 2CHBrCO 2H
ClCH 2CH 2CH 2CO 2H
CH 3CCl 2CO 2H
C 6H 5CH 2OH
C 6H 5CO 2H
C 6H 5OCH 3
C 6H 5OH
OH
O
CO2H
O
(c)
NH2
(d)
N—H
N — CH3
O
N—H
O
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10.
In the two questions below, you are asked to rank the relative strengths of illustrated acids
and bases. Use your knowledge of resonance and inductive to answer this.
A.
For the series of bases shown below, rank the set from strongest to weakest.
Strongest
N
(i)
N
H
N
(a)
N
H
N
(c)
(b)
Weakest
(d)
Strongest
N
(ii)
N
OMe
(a)
B.
N
N
(c)
(b)
Weakest
(d)
For the series of acids shown below, rank the set from strongest to weakest.
HO
OMe
(ii)
(c)
(b)
Weakest
(d)
Strongest
HO2C
HO2C
HO2C
NO2
NO2
OMe
(a)
CN
NO2
(a)
HO2C
Strongest
HO
HO
HO
(i)
11.
N
NMe2
(c)
(b)
(d)
Weakest
In each of the following sections four compounds are listed. (Decreasing order of acidic
strength, 1 is strongest & 4 is weakest).
(a)
(b)
(c)
CH 2(CO 2C 2H 5 )2
CH 3COCH 2CO 2C 2H 5
(CH 3CO)2 CH 2
RC ºº CH
RCH 2NO 2
RSO 2CH 3
(C 6H 5 )3 CH
RCOCH 3
CH 2(C ºº N)2
CH 2(NO 2 )2
HC ºº N
RCH 2CO 2C 2H 5
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42
O
S
CH2
(d)
CH2 ;
CH2
CH2
S
O
12.
Rank in the order of increasing basic strength.
NH2
A. (a)
N
(b)
H
(c)
N
O
O
O
H
H
H
N
N
B. (a)
(b)
(c)
(d)
N
H2N
H
H
H
N
||
C
C. (a)
H2N
13.
N
||
C
(b)
H2N
NH2
H
H
N
||
C
(c)
CH3
H2N
N
||
C
(d)
H3C
OH
CH3
Compare acidic strength of the following (Write your answer in box).
OH
OH
OH
A.
(a)
(b)
(c)
OH
OH
OH
H3CO
H2N
B.
F3 C
(a)
(b)
(c)
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Cl
F
Br
OH
Cl
OH
Cl
OH
F
C.
F
Br
Br
(a)
(b)
O
(c)
O
O
O
O
D.
O
O
O
(a)
O
(b)
O
O
(c)
(d)
O
O
O
O
E.
O
(a)
O
(b)
(c)
H
H
H
F.
(a)
14.
(b)
(c)
Arrange the hydrogens in increasing order of their acidic strengths.
O
A.
Ha
O
F
B.
O
|
Hb
O
Hc
F
Hc
H
Hb
O
O
Ha
H
H
Hd H
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44
15.
The compounds whose structures are shown below, incorporate a variety of functional
groups. The question on the right ask you to identify which compounds have a specific
functional group. For each compound that has the designed group, enter the appropriate
number. The aromatic rings should not be counted as double bonds.
CH2
O
H3 C
CH3
H3C
CH3
CH3
N
CH2
1. limonene
H
O
CH3
N
CH3
CO2H
5. camphor
4. ibuprofen
3. nicotine
2. muscone
O
CH3
O
OH
H3C
OH
HO
O
O — CH3
O—H
6. vanillin
CH3
H3C
O
N
H
O
H3C
7. aspirin
A.
Which have carbon-carbon double bonds ?
B.
Which have a ketone carbonyl group ?
C.
Which have an aldehyde carbonyl group ?
D.
Which have aromatic rings ?
E.
Which have a hydroxy group ?
F.
Which have ether groups ?
G.
Which have an ester group ?
H.
Which have an amide group ?
I.
Which have a carboxylic acid group ?
CH3
8. geraniol
9. acetaminophenol
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45
16.
Problem
A
B
O
C
CO2H
1
D
O
CH2OH
OH
OH
OCH3
OH
2
O2N
O
3
N— H
N— H
N— H
N — CH3
O
O
H
H
4
C
H
A.
(c) C
(d) D
(b) B
(c) C
(d) D
(b) B
(c) C
(d) D
(b) B
(c) C
(d) D
(b) B
(c) C
(d) D
(b) B
(c) C
(d) D
(c) C
(d) D
(c) C
(d) D
Which is the strongest acid in 4 ?
(a) A
H.
(b) B
Which is weakest acid in 3 ?
(a) A
G.
CO2H
Cl
Which is the strongest acid in 3 ?
(a) A
F.
H
Cl
C
Which is weakest acid in 2 ?
(a) A
E.
CO2H
Which is the strongest acid in 2 ?
(a) A
D.
C
CO2H
Which is weakest acid in 1 ?
(a) A
C.
CO2H
Cl
Which is the strongest acid in 1?
(a) A
B.
H Cl
(b) B
Which is weakest acid in 4 ?
(a) A
(b) B
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17.
For each of the six structural formulae (A through F), shown below, five questions are posed.
The answer to each is a number that should be entered in the appropriate answer box.
CH2
—C
N
C—CO2H
N
O
H3C
CH2
A
B
C
CH3
O
S
N— H
H2C
C
N
CH—C
N—CH3
OH
H3 C
H3C
D
A.
E
D.
F
(i) Number of sp 3 carbons : B. Number of sp 3
.................
CH3
C. Number of sp 3
carbons : ..................
carbons : ............
(ii) Number of sp 2 carbons :
Number of sp 2 carbons :
Number of sp 2 carbons :
..................
(iii) Number of sp carbons :
..................
(iv) Number of carbon-carbon
s -bonds : ...............
(v) Number of p-bonds to
carbon : .....................
..................
Number of sp carbons :
..................
Number of carbon-carbon
s -bonds : .................
Number of p-bonds to
carbon : ....................
..................
Number of sp carbons :
................
Number of carbon-carbon
s -bonds : ..................
Number of p-bonds to
carbon :.......................
(i) Number of sp 3 carbons : E. Number of sp 3
...............
F. Number of sp 3 carbons :
carbons : ...............
2
2
(ii) Number of sp carbons :
Number of sp
...............
(iii) Number of sp carbons :
...............
(iv) Number of carbon-carbon
s-bonds : ...............
(v) Number of p-bonds to
carbon : ...............
carbons : ...............
Number of sp carbons :
...............
Number of carbon-carbon
s -bonds : ...............
Number of p-bonds to
carbon :...............
...............
Number of sp 2
carbons : ...............
Number of sp carbons :
...............
Number of carbon-carbon
s -bonds : ...............
Number of p-bonds to
carbon :...............
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47
18.
Match the column (I) and (II). (Matrix)
Column (I)
Column (II)
Molecule
Property
(a)
(p)
cis-compound
(b)
(q)
trans-compound
(c)
(r)
Highest heat of combustion
(d)
(s)
lowest heat of combustion
19.
Match the column (I) and (II).
Column (I)
Column (II)
pK a of Conjugate acid
Molecule
(a)
N
O
(p)
0.8
(q)
5.33
(r)
10.65
(s)
10.95
H
(b)
N
CH2 — CH3
(c)
N
(d)
N
O
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48
20.
The junctures centred on atoms A, B and C on the given structure.
B
A
2
A.
(b) B
(c) C
(d) Cannot be predicted
Of the carbon-carbon bonds, (shown above) numbered from 1 to 4, which represent the most
favourable site for H 2 addition ?
(a) 1
21.
4
Which juncture has the greatest deviation from planarity ?
(a) A
B.
C
3
1
(b) 2
(c) 3
(d) 4
Select the most stable structure in each of the following
Part (A)
(a)
(b)
(c)
(d)
(b)
(c)
(d)
Part (B)
(a)
Part (C)
22.
(a) H 2C == CH — CH == CH — CH 3
(b) H 2C == C == CH — CH 2 — CH 3
(c) H 3C — CH == C == CH — CH 3
(d) H 2C == CH — CH 2 — CH == CH 2
Match the column I and II. (Matrix)
Column (I)
(a)
23.
Column (II)
—NO 2
–
(p)
- m effect
(q)
+ m effect
(b)
—O
(c)
— O — CH 3
(r)
+ I effect
(d)
— C ºº N
(s)
- I effect
Match the column I and II. (Matrix)
Column (I)
Column (II)
(a)
H 3C — CH == CH — CH 3
(p)
Dipole (cis > trans)
(b)
H 3C — CH == CH — CN
(q)
Dipole (trans > cis)
(c)
H 3C — CH == CH — Cl
(r)
Melting point ((trans > cis)
(d)
Cl — CH == CH — Cl
(s)
Boiling point (cis > trans)
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24.
Identify the most stable structure in each of the following :
Part (A)
CH3
CH 3
C
(a)
H
(c)
(b)
CH3
H
CH3
(d)
C
H
H
H
C
H
Part (B)
CH3
H
(a)
C
H
C
C
(d) H
CH2
C
H
H
CH3
H
C
C
H
H
CH3
H
H
C
C
H
(c)
C
(b)
H
CH2
C
CH3
Part (C)
CH2
(c)
(b)
(a)
(d)
Part (D)
(a)
(b)
(c)
(d)
Part (E)
CH 3
(a)
H
C == C
H
(c)
(b)
CH 2 — CH 2 — CH 3
H
H
H
C == C
H
CH 3
C == C
H
CH 3
H
CH 3
C == C
(d)
H
H
CH 3
Part (F)
CH2
CH2
(a)
(b)
CH2
(c)
(d)
CH2
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Part (G)
H
H
H
H
+
(a) CH2
H
H
H
O
H
H
CH3
(b)
H
+
H
H
O
H
H
H
25.
H
H
H
H
H
H
(c) H
H
H
H
H
H
(d) H
O
H
H
H
O
H
H
H
H
Identify the most basic compound in the following.
Part (A)
O
NH
O
NH
(a)
NH
(b)
NH
NH
(c)
NH
(d)
O
Part (B)
NH2
NH — CH3
NH2
(a)
N
(b)
(c)
(d)
(b) NaOOCCH 3
(c) NaOCH 3
(d) NaNH 2
Part (C)
(a) NaOH
Part (D)
NH2
NH2
(a)
(b)
NH2
(d)
(c)
NO2
NH2
OCH3
Cl
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51
26.
Identify the most acidic hydrogen containing compound from the following.
Part (A)
(b)
(a)
(c)
CH3
(d)
H
NMe3
H
PMe3
Part (B)
O
O
(d)
O
O
CO2Et
(a)
O
(c)
(b)
O
C — O — Et
O
Part (C)
OH
OH
OH
(c)
(b)
(a)
OH
(d)
NO2
CH2CH3
NH — CH3
NO2
Part (D)
O
O
O
(b)
(a)
O
O
(c)
O
(d)
O
O
Part (E)
OH
O
CH2 — NH3
(a)
C — OH
(c)
(b)
CH2OH
(d)
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Part (F)
(a) CH 3CH 2OH
(b) CH 3CH 2NH 2
(c) CH 3 — C ºº CH
(d) CH 3 — CH == CH 2
Part (G)
NH3
NH3
(b) CH 2 — CO 2H
|
NH 3
Å
(a) CH 3 — CO 2H
(c)
(d)
Part (H)
OH
OH
OH
OH
NO2
(b)
(a)
(c)
(d)
NO2
NO2
NO2
NO2
NO2
Part (I)
CH
CH
(d)
(a)
(c)
(b)
27.
N
1
C
O1
H
CH2
C3
C2
H
H
Give the type of hybridization present at each atom.
(i) N —...................
(iv) O 1 —...................
(ii) C 1 —...................
(v) CH 2 —...................
(iii)C 2 —...................
(vi) C 3 —...................
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28.
Predict the direction of the following equilibrium. Write your answer in the box given below.
H
(a)
Å
+ Ph 3 C Br
H
(A)
º
+ CH 4
Br –
+ Ph 3 CH
(C)
£
(D)
º
K+
H
H
(B)
(b)
29.
–
Å –
+
H
K CH 3
£
H
Match the column I and II. (Matrix)
Column (I)
Column (II)
O
(a) NaHCO 3 will react with
OH
(p)
OH
O
Squaric acid
O
(b) Na will react with
(q)
(c) NaOH will react with
(r)
C — O — H
OH
O
(d) NaNH 2 will react with
S — O — H
(s)
O
30.
Match the column I and II.
Column (I)
Column (II)
Acid
(a) CH 3 — CO 2H
Å
(b) (CH 3 )3N CH 2CO 2H
pK a
(p)
5.69
(q)
4.27
(r)
1.83
(s)
4.80
Å
(c) (CH 3 )3 N(CH 2 )4CO 2H
–
(d) O 2 C — CH 2 — CO 2H
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31.
Match the column I and II.
Column (I)
Column (II)
O
(a)
C — O — H + NaHCO3¾®
NH 3
(p)
14
O
14
(b)
C — O — H + NaHCO 3¾®
14
(q)
CO 2
O
(c)
C — O — H + Na
¾®
(r)
CO 2
(s)
H2
O
S — O — H + NaNH2
(d)
O
CO2H
SO3H
14
NaH CO
NaHCO
3
3
¾ ¾¾¾
® ( A) + ( B ) ¾ ¾¾¾
® ( C ) + ( D)
32.
gas
OH
gas
CH — OH
C
CH
Sum of molecular mass of gas (A + C) is :
(a) 88
33.
(b) 90
(c) 92
(d) 40
O
||
NaHCO 3
®( A) gas
Ph — C — O — H ¾ ¾¾¾
Na
Ph — C ºº CH ¾ ¾
¾®( B ) gas
NaNH
2
®(C ) gas
Ph — OH ¾ ¾¾¾
NaH
R — O — H ¾ ¾¾®( D) gas
Sum of molecular mass of gas A + B + C + D is :
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34.
Match the column I and II.
Column (I)
Column (II)
Molecule
O
Rotational free energy barrier
Ph
(a)
Ph
(p)
180 kJ mol
(q)
88.3 kJ mol
(r)
21 kJ mol
(s)
Negative barrier
O
Ph
Ph
(b)
Ph
Ph
Ph
(c)
Ph
Cl
Cl
Cl
Cl
Ph
Ph
H
(d)
C == C
H
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35.
Consider the following reaction of boron trifluoride (BF3 ) and acetone :
O
+
BF3
A.
¾®
CH3
What is the critical HOMO (nucleophile) of this reaction ?
(a) non-bonding orbital on boron
(c) p-orbital of acetone
B.
(b) s-orbital of acetone
(d) non-bonding electron pair orbital on oxygen
What is the critical LUMO (electrophile) of the reaction ?
(a) p-orbital of BF3
(c) p * orbital of acetone
C.
Product
CH3
(b) s-orbital of BF3
(d) non-bonding electron pair orbital on oxygen
Which of the following is the correct product of this reaction ?
(Lone electron pairs are not shown explicitly).
O
BF3
O
(a)
(b)
CH3
36.
O
BF3
O
(c)
BF3
(d)
CH3
CH3
BF3
Rank the following carbocations according to stability (1 = most stable, 5 = least stable).
..
:OCH3
+
+
A
+
B
C
+
+
D
E
Put the answer in the boxes.
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57
37. Among the given molecules, identify aromatic, anti-aromatic and non-aromatic molecules.
Q
(1)
+
Å
(2)
(3)
(4)
+
Q
(5)
(6)
(7)
Q
Q
O
(8)
Å
(9)
(10)
(11)
(12)
B
|
H
(13)
O
O
B
|
H
(14)
(15)
O Å O
(16)
S
O
Å
(17)
(18)
(19)
N
|
H
O
Q
Å
(21)
(20)
O
(22)
(23)
O
(24)
O
O
O
O
O
N
(25)
(26)
(27)
O
N
|
H
(28)
N
O
N
H
N
(29)
N
(30)
(31)
N
Å
(32) N
N—H
N
H
H
Q
(33)
Å
M—N
N—H (34)
N
N—H
(35)
(36)
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CH3
|
B
(37)
(38)
(39)
(40)
Q
N
N
|
H
N
(41) N
:S:
(42)
(43)
N
O
N
N
H
N
(44)
N
B
H–N
(45)
(46)
B
N–H
N
|
H
(47)
B
(48)
Q
Borazole
Å
Q
CH2
(49)
CH2
(50)
(51)
O
O
(52)
(53)
(54)
(55)
N
O
(56)
N
(57)
(60)
H
CH2
(58)
(59)
(61)
Q
(62)
I
(63)
(64)
(65)
(66)
D
D
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59
38.
Among the given pairs, which is more reactive towards AgNO 3 (or) toward hydrolysis.
Compound (A)
O
Compound (B)
O
Br
Put the
Answer
here
Br
1.
Br
Br
2.
O
I
I
Br
Br
3.
4.
Cl
5.
6.
CH 3 - O - CH 2 - Cl
Cl
CH 3 - CH 2 - CH 2 - Cl
Br
CH2–Br
7.
Br
Br
8.
Br
Br
9.
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60
CH2–Cl
Cl
10.
39. Put the answer in boxes given as directed.
S.No.
Property
A.
highest boiling
point
B.
highest boiling
point
C.
most soluble
in water
D.
highest
solubility in
benzene
Name of
force
Correct responsi
Answer ble for
the
property
Molecules
NCl3 ClNH2
NH4Cl NH3
CH3
OH
NH
OH
SH
OH
SH
NH
40. Circle any conjugated portions of these molecules.
CH2 = C = CH – CH = CH2
CH3O
(A)
(B)
(C)
(D)
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41. Arrange in the order as directed A.
The given alkenes in the order of their stability (1- most stable, 3-least stable).
A
B
C
B. Arrange the following in the order of their acidic strength (1-most acidic, 4-least acidic)
OH
A
B
O
C
D
C. Arrange the following molecules in order of expected boiling point. (1=highest bpt ;
4=lowest bpt.)
OH
OH
A
D.
O
B
C
D
Arrange the following alkenes in order of their stability. (1 = most stable ; 5 = least stable).
A
B
C
D
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62
42. Match the column. (Matrix)
Column (I)
Column (II)
Compounds
Number of Benzylic hydrogen
(a)
(p)
2
(q)
3
(c)
(r)
4
(d)
(s)
5
CH2–CH3
CH3
(b)
CH3
43. Identify (+M) mesomeric & (–M) group of following.
+M
–M
–I
+I
N
N
O
O
||
C – NH – CH3
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O
||
C – NH – CH3
O
||
C – CH3
NO2
OCH3
CH = O
O = C – OH
NH – CH3
44. Identify the following solvents as polar protic (PP), polar aprotic (PA), non-polar protic
(NPP) or non-polar aprotic (NPA).
O
||
S
O
||
S
A
B
O
H
NH2
C
N
D
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64
45. Identify the stronger nucleophile in each pair.
(i)
(iii)
A
B
O
O
A
(ii)
Q
NH
B
A
O
B
NH
Q
NH
(iv) NH 3
A
CH 4
B
46. Encircle the molecule as directed :
(a) Which has higher boiling point : HBr or HCl
(b) Which has a higher boiling point : CH 3 – CH 2 – OH or CH 3 – CH = O
(c) Which is more miscible with methanol (CH 3 OH) : CH 3 – CH 2 – CH 2 – CH 2 – CH3
or CH 3 – CH 2 – CH 2 – CH 2 – CH 2 – CH3
(d) Which has a higher melting point : CH 4 or CH 3 – CH 2 – CH 3
CH3
|
(e) Which has a higher boiling point : CH 3 – CH 2 – CH 2 – CH 2 – CH3 or CH —CH —CH
3
2
3
|
47. Encircle the molecule as directed :
CH3
(a) Which is more stable : BH 3 or BF3
(b) Which is a stronger base : HO - or H 2O
(c) Which is a stronger base : HO - or HS (d) Which is a stronger acid : HCl or HI
(e) Which is a stronger acid : HOCl or HCl
48. Explain why A has lower boiling point than B ?
F3C–CF2
CF3
F
CF3
(B)
b.p. = 67ºC
(A)
b.p. = 58ºC
49. Arrange the protons shown in the decreasing order of their approximate bond energies.
Hc
Hb
Ha
Hd
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50. Consider the H-atoms in the molecule given below and answer the following.
Hb
He
Hd
Hc
Ha
(A) Identify the type (1° , 2° or 3° alkyl, vinyl, allyl etc.) of these H-atoms.
(B) Arrange them in the decreasing order of their case of abstraction (easiest first)
51. Consider the molecule shown below and answer with respect to H a ¾® H e
He
Hd
Ha
Hc
Hb
(A) Identify the type of H-atom (1°, 2°, 3° alkyl, vinyl or allyl)
(B) Arrange them in decreasing order of their bond energy.
52. Rank the following carbocations in order of stability (1 = most stable).
2º
3º
3º
+3º
+ 3º
+ 2º
2º
A
2º +
B
C
D
53. Rank the following alkenes according to energy (1 = lowest energy).
A
B
C
D
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66
54. Match the column:
Column (I)
Column (II)
(Compounds)
(Double bond equivalent value)
(a)
(p)
11
(b)
(q)
12
(r)
13
(s)
14
(t)
15
O
(c)
O
O
(d)
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67
Subjective Problems
1. How many 2º carbon in the following ?
C ==C ==C
2. Find out the double bond equivalent (DBE) value of the given following compound:
O
O
NH2
ºº N
O
3. Total number of functional groups present in the given following compound :
O
O
4. Total number of a-hydrogen in the given following compound is:
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68
5. How many carbon atom present in the parent chain in the given following compound?
O
CH3
6. Total number of DBE value in :
7. How many isomers of C 4H 10O reacts with Na metal to evolve H 2 gas ? (excluding
stereoisomer)
8.
O
O
O
O O
[x]-crown-[y]-ether.
x +y
value of
=?
3
9. Which of the given following compound will react with NaHCO 3 or soluble in NaHCO 3 ?
O
OH
(a)
OH
(b)
C—OH
(c)
OH
O ==S ==O
(d)
(e) CH 3 — C ºº CH
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69
10. How many compound are stable after deprotonation ?
N
(a)
(e)
OH
(b)
(f)
O
O
(c)
(d)
r
O
O
OH
NH2
11.
O
N
Sum of types of functional group and DBE value for given compound is X so the value of
X - 10 is
12. P = Number of anti-aromatic compound, so the value of x is :
CH 3
O
N
N
O
Q = Total number of resonating structures of carbonate ion [CO 23 ]
H3C r CH3
R = Number of a-hydrogen in given carbocation
S = Total number of geometrical isomers of CH 3 — CH == CH — CH == CH 2
T = Number of compound more acidic then CH 3CH 2OH
OH
OH
,
, CH 3COOH , CH 3SO 3H
NO2
Sum of ( P + Q + R + S + T ) - 15 is :
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13. x = number of ( +M ) group attached with phenyl ring, so the value of x is.
OH
(a)
NH2
(b)
O
C—CH 3
NO2
(c)
(d)
NH—CH3
OCH3
(e)
(g)
(f)
O
O
S—OH
C—H
O
(h)
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ANSWERS — LEVEL 2
1.
a – 4; b – 3; c – 2; d – 1
2.
a – 3; b – 2; c – 1
3.
A – B; B – E; C – A; D – F
4.
A – a, c, f, g, k, l; B – b, d, h, j; C – e, i
5.
A –d; B – a
6.
C<B<A
7.
a – 2, 1, 4, 3; b – 1, 2, 3, 4 ; c – 3, 4, 1, 2; d – 3, 2, 4, 1
8.
a – iv > ii > i > iii; b – iii > iv > i > ii
9.
a – 4, 2, 3, 1; b – 3, 1, 4, 2; c – 2, 1, 3, 4; d – 2, 3, 4, 1
10.
A (i) – d > b > c > a;
(ii) – c > a > b > d
B (i) – c > d > b > a;
(ii) – b > d > c > a
11.
(a) 3 2 1 4; (b) 2 1 4 3;
12.
A – c < a < b; B – b < a < c < d; C – d < b < c < a
13.
A – c < a < b; B – a < b < c; C – c < b < a; D – d < c < a <b; E – c < a < b; F – a > b > c
14.
A – Hc < Ha < Hb; B – Hd < Hc < Hb < Ha
15.
A – 1, 3, 4, 6, 7, 8, 9; B – 2, 5; C – 6; D – 3, 4, 6, 7, 9; E – 6, 8, 9; F – 6; G – 7; H – 9; I – 4,7
16.
A – b; B – a; C – d; D – b; E – a; F – d; G – d; H – a
17.
(c) 3 1 2 4; (d) 3 4 1 2
(i)
(ii)
(iii)
(iv)
(v)
A
6
4
0
10
2
B
0
7
2
9
6
C
5
1
0
5
1
D
1
3
1
3
4
E
2
3
0
2
2
F
10
0
0
10
0
18.
a – q; b – p, r; c – p, s; d – q
19.
a – p; b– r; c – s; d – q
20.
A – c; B – d
21.
A – b; B – b; C – a
22.
a – p, s; b – q, r; c – q, s; d – p, s
23.
a – p, r, s; b – q, r; c – q, r; d – p, r, s
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24.
A – b; B – c; C – a; D – c; E – a; F – b; G – d
25.
A – d; B – a; C – d; D – c
26.
A – c; B – b; C – b; D – b; E – b; F – a; G – b; H – c; I – b
27.
i. – sp; ii – sp; iii –sp 2 ; iv – sp 2 ; v – sp 3 ; vi – sp 3
28.
a – forward
29.
a – p. q, s; b – p, q, r, s; c – p, q, r, s; d – p, q, r, s
30.
a – s; b – r; c – q; d – p
31.
a – r; b – q; c – s; d – p
32.
b
33.
65
34.
a – q; b – r; c – s; d – p
35.
A – d; B – a; C – a
36.
A - 3; B - 1; C - 5; D - 2; E - 4
37.
Aromatic— 3, 4, 5, 9, 12, 13, 15, 16, 17, 19, 22, 24, 25, 26 ,27, 28, 29, 31, 32, 33, 34, 35, 37,
38, 39, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51 , 53, 54, 56, 57, 58, 61, 62, 63, 66
b – backward
Non-aromatic— 1, 6, 7, 8, 18, 20, 23, 30, 40, 55, 64, 65
Anti-aromatic— 2, 10, 11, 14, 21, 36, 52, 59, 60
38.
1 - B; 2 - A; 3 - B; 4 - A; 5 - A; 6 - A; 7 - B; 8 - B; 9 - A; 10 - A
39.
A. NH 4 Cl, cation-anion interactoin
B.
CH3, van der Waals’ forces
OH
C.
, H-bonding (Also dipole-dipole)
D.
NH, Aromatic stacking
OH
CH2 = C = CH – CH = CH2
40.
CH3O
41.
42.
A. A - 3, B - 2, C - 1,
B.
A - 1, B - 3, C - 2, D - 4
C. A - 3, B - 1, C - 4, D - 2
D.
A - 1, B - 2, C - 3, D - 4
a - s; b - r ; c - q; d - p
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43.
+M
(1)
(2)
N
N
O
–M
–I
+I
×
×
×
×
O
||
C – NH – CH3
(3)
×
×
×
×
×
×
O
||
C – 3CH
(4)
NO2
(5)
OCH3
(6)
×
×
CH = O
(7)
×
×
×
×
O = C – OH
(8)
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NH – CH3
(9)
×
44.
A - PA; B - PP; C - NPA; D - PA
46.
(a) HBr ;
(d)
45.
(b) CH3 – CH 2 – OH ;
CH3 – CH2 – CH3
;
×
(i) B, (ii) B, (iii) B, (iv) A
(c) CH3 – CH2 – CH2 – CH2 – CH3 ;
(e) CH3 – CH2 – CH2 – CH2 – CH3
47.
(a) BF3 ;
48.
In A, highly electronegative F-atoms are present at the periphery. In liquid term these
F-atoms will repel each other due to partial negative charge and thus A will have lower b.pt.
49.
Hd > Ha > Hb > Hc
50.
A– H a =1° alkyl; H b = 2° alkyl; H c =2° allyl; H d = vinyl; H e = 3° allyl
(b) HO¯ ;
(c) HO¯ ;
(d) HI ;
(e) HOCl
B– Easiest to abstract: H e > H c > H b > H a > H d Hardest to abstract
51.
A– H a = 2° alkyl; H b = 2° allyl; H c = vinyl; H d = 3° allyl; H e = 1° alkyl
B– H c > H e > H a > H b > H d
52.
A–2; B–1; C–3; D–4
54.
a-r; b-t; c-t; d-s
53. A–1; B–4; C–3; D–2
Subjective Problems
1. 21
9. 2 (c, d)
2. 11
3. 3
4. 6
10. 3 (a, c, f)
5. 4
6. 13
7. 4
8. 7
11. 7
12. P = 3, Q = 3, R = 7, S = 2 , T = 4 = 19 - 15 = 4
13. 4
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2
ISOMERISM
(Structural & Stereoisomerism)
Level - 1
replace Ha with D and Hb with H
CH3
1.
Ha
Hb
H
Br
replace Hb with D and Ha with H
CH3
(Y)
Relation between (X) and (Y) is :
(a) enantiomers
(c) E and Z isomer
2.
(X)
(b) diastereomers
(d) constitutional isomer
Which of the following cyclopentane derivative is optically inactive ?
OH
H
(a)
OH
H
(b)
H
H
OH
H
(e)
OH
CH3
OH
H
H
CH3
CH3
(d)
CH3
(c)
H
H
H
CH3
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76
3.
Which is the most stable conformer along the 2, 3 C – C bond axis of the compound ?
F
HC
3
F
H
(a)
CH3 H
4.
H
CH3
H
HC
3
F
H
CH3
CH3
CH3 (b) H
H3C
H
CH3
H3C
F
(d) H3C
H
H
H
CH3 (c) F
CH3 CH3
H3C
Assign double bond configurations to the following :
COOH
NC
CH2OH
CN
H2N – H2C
(a) E
5.
(b) Z
(c) E, E
(d) Z, Z
Allegra, a common prescription drug with the structure shown below, is given for the
treatment of seasonal allergies. How many stereogenic carbon does Allegra possess ?
CH3
COOH
CH3
H
N
OH
HO
(a) 1
6.
7.
(b) 2
(c) 3
(d) 4
How many meso isomers of C4H8Cl2 will be ?
(a) 0
(b) 1
(c) 2
(d) 3
The stable form of trans-1, 4-dimethylcyclohexane is represented as:
CH3
CH3
(a)
(b)
CH3
(c)
H3C
CH3
CH3
CH3
(d)
CH3
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8.
9.
Which of the following compound is non-resovable (meso) compounds ?
OH
Br
Br
H
Br
OH
Me
Br
H
H
H
(a) H
(b)
(c) H
(d) All of these
Br
H
H
H
Br
HO - CH 2 - CH 2 - F
( 2)
( 3)
Which conformer of above compound is most stable across C 2 - C 3 ?
(a) staggered
(b) eclipsed (partially)
(c) gauche
(d) fully eclipsed
10.
The following molecule is fluorometholone, a steroidal anti-inflammatory agent. How many
stereogenic centers does it contain ?
O
H3C
HO
CH3
OH
H
H3C
F
H
fluorometholone
O
CH3
(a) 5
11.
(b) 6
(c) 7
How many chiral carbons are there in Reserpine (an antipsychotic drug) ?
O
N
O
O
N
H
O
O
(a) 9
O
O
O
12.
(d) 8
(b) 8
O
(c) 7
(d) 6
How many chiral centers are in the following compound ?
O
O
(a) 4
13.
(b) 5
(c) 6
(d) 7
Among the following, the optically inactive compound is:
O
S
N
(a) H3CH2C
(b)
CH3
H3C
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H3C
CH3
(c)
(d)
H
COOH
HO
O
OH
*
traces of base
14.
(A) ; Unknown compound (A) is :
14
(C = C )
O
15.
O
*
(a)
OH
OH
O
*
(b)
O
OH
(c)
(d)
Which of the following compounds might be useful to the chemist trying to
increase the optical purity of the (d) sample ?
HO2C
CO2H
(a)
(b)
CO2H
HO
HO2C
CO2H
(c)
16.
(d)
CO2H
Which of the following molecules is (are) chiral ?
H
CH3
Cl
H
C
(II)
(I)
O
(III)
O
O
(V)
(a) I and II
(IV)
H
H3C
O
H
H
CH(CH3)2
Br
H
H3C
H
(VI)
(b) III and IV
(c) II, IV and VI
(d) I, II, III and VI
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17.
The structure of (S)-2-fluorobutane is best represented by :
F
F
C–H
|
H
C
(b) 3
(a) CH 3 C HCH 2CH 3
CH2CH3
H
CH3
C–F
(c) H3C
18.
(d)
CH2CH3
How are the following compounds related ?
Br
H3C
Br
H
19.
20.
H
CH2CH3
CH3
Br
(a) Diastereomers
(c) Meso compounds
H
(b) Enantiomers
(d) Identical
Which one of the following is chiral ?
(a) 1, 1-Dibromo-1-chloropropane
(c) 1, 1-Dibromo-3-chloropropane
(b) 1, 3-Dibromo-1-chloropropane
(d) 1, 3-Dibromo-2-chloropropane
Among the following, the Newmann projections of meso-2, 3-butanediol are :
Me
Me
Me
Me
OH
OH
H
Me
HO
Me
H
H
H
HO
Me
P
(a) P, Q
21.
Br
F
OH
H
Me
Q
(b) P, R
HO
H
H
R
(c) R, S
H
OH
OH
S
(d) Q, S
The binaphthol (Bnp) is:
OH
OH
(a)
(b)
(c)
(d)
an optically active compound having chiral centre
an optically inactive compound
a meso compound
an optically active compound without having chiral centre
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22.
Which of the following pairs of compounds is a pair of enantiomers ?
Br
Br
(a)
(b)
Cl
Cl
Cl
(c)
(d)
Cl
23.
Br
Determine the absolute configurations of the labeled carbons (a and b):
(a) a = R ; b = R
(c) a = S ; b = R
b
Cl
(b) a = R ; b = S
(d) a = S ; b = S
Which of the structures (a – d) will be produced if a “ring flip” occurs in the following
compound in chair form ?
(a)
(b)
(c)
(d)
Which of the following compounds is most stable ?
(a)
28.
(d) 16
(b) diastereomers
(d) none of the above
a
27.
Cl
The following pair of compounds is best described as :
Cl
26.
Cl
Br
(c) 10
(b) 8
(a) identical
(c) enantiomers
25.
Cl
The maximum number of stereoisomers that could exist for the compound below ?
Br Br
(a) 6
24.
Cl
(b)
(c)
(d)
Which is the most stable chair form of this compound ?
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(a)
29.
(b)
(c)
Ph
Ph
(I)
H
CO2–
CH3
CH3
H
NH3
H
NH3
(II) H
Ph
–
Ph
Ph
(III) NH3
COO
CH3
CH3
CH3
H
(IV) Ph
CH3
–
CO
CH3
(b) I & III
(c) I & II
The following compounds differ in respect of :
OH
O
HO
HO
31.
H
COO–
(d) II & IV
OH
O
HO
OH
HO
(a)
(b)
(c)
(d)
CH3
H
2
(a) I & IV
Ph
NH3
Ph
H
30.
(d)
Which pairs of the salts would have identical solubilities in methanol ?
OH
OH
OH
their chemical and physical properties
nothing
the direction in which they rotate plane of polarized light
their interactions with molecules
Indicate whether each of the following pairs are identical, or ?
F
Br
(I)
H
H
CH3
H
H3C
CH3
Br
Br
(III) CH3
H
H
(a)
(b)
(c)
(d)
Cl
CH2CH3
CH3 Cl H
H
I
enantiomers
identical
enantiomers
enantiomers
(II)
F
H
CH3
Br
H
CH2Br
Cl
H
H
Cl
CH3 CH CH
2
3
H
CH3
Br
II
diastereomers
enantiomers
diastereomers
identical
III
enantiomers
enantiomers
identical
identical
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32. Which of the following is achiral ?
33.
(a)
(b)
(c)
(d) a molecule of 3-methylheptane
Which of the following compounds are meso forms ?
CH3
CH3
H
OH
H
Cl
H
OH
Cl
H
CH2CH3
CH3
CH3
CH3
1
3
2
(a) 1 only
(c) 1 and 2
(b) 3 only
(d) 2 and 3
34.
The separation of a racemic mixture into pure enantiomers is termed as :
(a) Racemization
(b) Isomerization
(c) Resolution
(d) Equilibration
35.
Rank of the following groups in order of R, S precedence (IV is highest) :
– CH(CH3)2
– CH2CH2Br
– CH2Br
– C(CH3)3
1
2
3
4
I
II
III
IV
I
II
III
IV
(a) 3
(c) 3
3
1
36.
2
4
4
1
1
2
(b) 1
(d) 3
4
4
2
2
Which of the following is a meso compound ?
H
(a)
(d)
Cl
H
H3C
Cl
H3C
Cl
H
Cl
Cl
CH3
H
CH3
(b)
(e)
H3C
Cl
H
Cl
H
CH2CH3
H
Cl
H3C
Cl
(c)
H
H3C
CH2CH3
H
Cl
CH2Cl
H
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37.
Among the following structures, select E isomers (arrows indicate the bonds to be
considered) ?
CH3 Cl
Br
Br
CH3
CH3
Cl H C
3
H
C
Br
3
O
F
D
O
H3C
H 3C
H3C
CH
CH3
3
CH 3
O
O
H
CH3
H
H3C
(1)
(2)
(3)
(4)
(a) 1 and 2
38.
39.
40.
(b) 1 and 3
(c) 1 and 4
Which of the following compounds has a zero dipole moment ?
Cl
Cl
Cl
Cl
Cl
(a)
(b)
(c)
(d)
Cl
Cl
Cl
Cl
On Pluto, where everything is frozen, astronauts discovered two forms of butane gauche and
anti. Assuming that there are no rotations around single bonds, which statement about the
two forms is correct ?
(a) They are enantiomers
(b) They are diastereoisomers
(c) They are meso compounds
(d) The gauche form has two stereogenic centers, and the anti has only one
Which of the following will show optical activity ?
COOH
OH
H
(A)
(B)
(C) H
H
HO
H
COOH
(E) 50/50 mixture of C and D
(a) A, D and E
(b) A and E only
41.
42.
(d) 2 and 3
CH2CH3
CH2CH3
OH (D) HO
HO
OH
H
CH2CH3
(c) B, C and D
H
CH2CH3
(d) All except C
Among the structure shown below, which has lowest potential energy ?
(a)
(b)
(c)
(d)
Which of the following molecules is/are chiral ?
OH
Br H Br H
(I)
(a) I
Cl (II)
(b) II
OH
OH
COOH
H
(III) HO
H
COOH
(c) III
(d) I, II
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43.
A compound was synthesized by a student, but its structure was not identified.
However, his wonderfully helpful instructor told him that it was a meso
compound with 5 carbons and 2 stereogenic centers. Which of the following
structures should the student consider as possibilities for his compound ?
Br
OH CO2H
(I) Br
(II) HO2C
Br
Br
OH OH
(V) Br
(IV)
(a) I, II, IV
44.
Br
(b) II, IV
(c) I, III, V
(d) II, IV, V
How many isomers are possible for the following molecule ?
H
CHCH = CHCOOH
H3C
(a) 1
45.
(III)
OH
(b) 2
(c) 3
(d) 4
Which of the following molecules are chiral ?
CH3
(I)
HO
CH3
HO
H
(II)
H
Cl
Cl
(III)
(IV)
F
Br
(a) I, II, III and IV
46.
(b) II, III and IV
Cl
Cl
Cl
(c) II and IV
(d) I and II
Which equilibrium is not rapid at room temperature ?
(a) Cl
Cl
Me
Br
Me
Me
(b)
Cl
Cl
Me
Br
CH
H 3
(c)
H3C
H
CH
H3C 3
(d)
H
H
H
H
H
H
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85
47.
Which is the lowest energy conformation of butane ?
CH
H 3
H3C
H
(a)
48.
H
H3C
H
H
(b)
CH3
CH3
CH3
H
H
H
H
H3C
H
(c)
(d)
H
H
H
H
H
H
CH3
Which of the structures given below are chiral ?
H
CH3 O
(I) O
Cl
O
H
CH3
H3C
O
(II) Cl
O
H
H
CH2OH
CH2OH
CH2OH
HO
H
(III) HO
HO
H
CH2OH
(IV)
H
HO
H
HO
H
HO
H
CH2OH
CHO
Fischer projections
(V)
CH3
(a) I, II, III
49.
(b) II, III, V
(c) II, III
(d) I, II
Which of the following carboxylic acids could be resolved by reaction with an
enantiomerically pure chiral amine ?
CO2H
NO2
(a)
(b)
O2N
O2N
NO2
HO2C
CO2H
CO2H
CO2H
(c)
(d)
HO2C
50.
CO2H
O2 N
NO2
NO2
What is the relationship between the molecules in the following pairs ?
CHO
H
H
HO
H
OH
OH
H
OH
CH2OH
CH2OH
and
HO
H
HO
HO
H
OH
H
H
CHO
(Fischer projections)
(a) enantiomers
(b) diastereomers
(c) identical
(d) structural isomers
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51.
What are the correct designations for the structure below ?
Cl
CO2H
(a) E, E
(c) E, Z
52.
(b) Z, E
(d) No geometrical isomers are possible
Which of the following molecules are chiral ?
OH
OH
(I)
(III) HO
(II)
(IV)
(V)
(a) I and III
(b) I and V
H
H
HO
OH
OH
53.
CH3
CH3
(c) II and III
(d) II, III, IV
Which one of the following isomeric structures has the lowest energy ?
(a)
(b)
(c)
(d)
(e)
54.
The following compounds are identical with respect to :
CH3
CH3
Cl
Cl
(a) molecular composition
(c) melting point
55.
(b) boiling point
(d) IUPAC name
Among the following, the most stable isomer is :
OH
OCH3
(a)
(b)
OMe
HO
(c)
56.
OMe
(d)
OH
OH
OMe
The most stable conformation of the following compound is :
Me
Me
t-Bu
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Me
Me
Me
(a) t-Bu
(b)
t-Bu
Me
Me
(c)
(d)
t-Bu
H
57.
H
Me
Me
Which of the following molecules have non-zero dipole moments ?
(I) gauche conformation of 1, 2-dibromoethane
(II) anti conformation of 1, 2-dibromoethane
(III) trans-1, 4-dibromocyclohexane
(IV) cis-1, 4-dibromocyclohexane
(V) tetrabromomethane
(VI) 1, 1-dibromocyclohexane
(a) I and II
(c) II and V
58.
Me
t-Bu
(b) I and IV
(d) I, IV and VI
What is the maximum number of stereoisomers possible for discodermolide ?
O
||
O–C–NH2
HO
O
O
OH
OH
OH
(a) 2 14
59.
(b) 2 15
(c) 2 16
(d) 2 17
An aqueous solution containing compounds A and B shows optical activity. A and B are
stereoisomers. Which of the following possibilities cannot be correct ?
(a) A has two chiral centers, but B does not have any because it has a symmetry plane
(b) A and B are enantiomers
(c) A and B are diastereomers
(d) A and B are not present in equal amounts
60.
Which of the following structures represents the lowest-energy form of (1S, 2S,
4R)-trimethyl -cyclohexane ?
(a)
(b)
(c)
(d)
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61.
Which one of the following is a diastereomer of (R)-4-bromo-cis-2-hexene ?
(a) (S)-4-bromo-cis-2-hexene
(b) (S)-5-bromo-trans-2-hexene
(c) (R)-4-bromo-trans-2-hexene
(d) (R)-5-bromo-trans-2-hexene
62.
The structural formula of cocaine is shown below. How many stereogenic carbon atoms are
there in this molecule ?
CH3
O
N
OCH3
O
O
(a) 1
63.
(b) 2
(c) 3
(d) 4
Which of the following statements best describes the stereochemical relationships of
compound I, II and III shown below ?
CHO
CHO
CHO
(I)
H
H
H3C
H
H
CH3
H
H
(II)
H
H
H
CH3
H3C
H
H
H
CHO
(a) All compounds are chiral
(III)
H
H
H
CH3
H
CH3
H
H
CHO
CHO
(b) None of the compounds is chiral
(c) I and II are meso compounds
(d) I and II are diastereomers, and III is a meso compound
(e) I and II are chiral
64.
What is the absolute configuration of the following molecules ? (NS = the molecule has no
center) Note : For the purpose of this question only, the order of stereocenters is not
specified ; i.e., R, S = S, R.
Cl
O
HO
O
(I)
(II)
H2C=N
(III)
O
CH=NH
O
Cl
F
(IV) Br
Br
F
Cl
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I
(a) R
(c) R
65.
II
III
R, S R
R, S NS
I
(b) R
(d) R
II
R, R
R, S
III
S
R
IV
R, R
R, S
The number of all the possible stereoisomers formed by the given compound is :
(a) 2
66.
IV
NS
NS
(b) 3
(c) 32
(d) 64
The relationship among the following pairs of isomers is:
O
O
(I)
(II)
Br
Br Br
H
H
H
Br
CHO
OH HO
H
H
CH2OH
H
CH2OH
(IV)
(III)
I
A: Constitutional
II
B: Configurational
III
C: Conformational
IV
D: Optical
(a) I - A,II - B,III - B,IV - D
(c) I - B,II - A,III - B,IV - D
67.
CHO
(b) I - A,II - A,III - B,IV - D
(d) I - B,II - B,III - A,IV - B
The structural formula of sativene is shown below. How many stereogenic centers are there
in this molecule ?
(a) 2
(c) 4
(b) 3
(d) 5
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68.
Which of the following is the least stable conformer of cyclohexane ?
(a)
(b)
(Boat)
(Chair)
(c)
(d)
(Twist boat)
69.
(Half-chair)
The S- enantiomer of ibuprofen is responsible for its pain-relieving properties. Which one of
the following structures shown below is (S)-ibuprofen ?
O
H
C – OH
C
(a)
C
(b)
CH3
H3C
H
C
C
(d)
C – OH
H3C
O
70.
O
O
||
C – OH
CH3
H
(c)
OH
C
H
Which of the following depict the same ?
Br
(a) 1 and 2
(c) 2 and 3
C
Cl
CH2CH3
CH3
CH2CH3
CH3CH2
C
Cl
H3C
C
CH3
Br
Cl
1
2
3
Br
(b) 1 and 3
(d) 1, 2, and 3
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71.
A naturally occurring substance has the constitution shown below. How many may have
this constitution ?
O
CH2OH
HO
HO
(a) 2
72.
CH == CHCH == CHCH2CH2CH3
(b) 8
(c) 16
(d) 64
The absolute configurations of the two centers in the following molecule are :
1
COOH
H 2 Br
H 3 CN
OH
(a) 2(R), 3(S)
(b) 2(R), 3(R)
(c) 2(S), 3(S)
(d) 2(S), 3(R)
73.
The total number of stereoisomer possible for 2, 3-dichloro butane :
(a) 2
(b) 3
(c) 4
(d) 5
74.
Which of the following structure is not meso-2,3-butanediol ?
OH
H
(a) H
CH3
H
CH3
(b) H
CH3
OH
OH
H
CH3
OH
CH3
H
HO
(c)
H
CH3
OH
(d)
OH
CH3
H
HO
CH3
75.
A solution of optically active 1-phenylethanol racemizes in acidified aqueous medium. It is
due to :
(a) enolization
(b) carbonium ion formation
(c) carbanion formation
(d) reversible oxidation-reduction
76.
The most stable conformation of ethylene glycol is :
(a) Anti
(b) Gauche
(c) Partially eclipsed (d) Fully eclipsed
CH3
H
H
OH
CH3
HO
77.
Br
H
C2H5
78.
C2H5
H
Br
The molecules represented by the above two structures are :
(a) identical
(b) enantiomers
(c) diastereomers
(d) epimers
The correct order of priority of groups -SCH 3 (I), —NO 2 (II), — C ºº CH (III) and
— CH 2C 6 H 5 (IV), on the basis of CIP classification, is (increasing order) :
(a) I, III, II, IV
(b) IV, III, II, I
(c) II, IV, I, III
(d) III, IV, II, I
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79.
The configuration at C-2 and C-3 of the compound given :
CH3
H
Cl
Cl
H
C2H5
(a) 2R, 3S
80.
(b) 2S, 3R
(c) 2S, 3S
(d) 2R, 3R
Amongst the following amino acids, the (R) - enantiomer is represented by :
COOH
CH
3
NH2
(b) H
COOH
(a) H2N
CH3
H
COOH
NH2
(c)
81.
H3C
H
(d) H3C
COOH
Which of the following is a meso compound ?
CH3
CH2 – CH3
H
H
Br
H
OH
Br
OH
(a) H
(b) H
(c)
CH2 -CH3
CH3
OH
NH2
H
H
(d) All of these
OH
82.
Predict stereochemistry of product when d and l-amine reacts with l-acid:
(a) Diastereomers
(b) Meso
(c) Racemic
(d) Pure Enantiomer
83.
How many chiral center (excluding N centres) are there in morphine?
HO
O
H
N
H
(a) 4
84.
85.
HO
(b) 5
CH3
(c) 6
Which dimethylcyclobutane is optically active ?
(a) trans-1, 2
(b) cis-1, 2
(c) trans-1, 3
(d) More than 6
(d) cis-1, 3
Which of the following is the enantiomer of the compound shown below ?
H
Me
Br
Br
H
Me
OH
Et
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(a)
H
Br
H
Br
HO
86.
87.
88.
(b)
Me
Br
Br
H
Br
(c) Br
Me
Me
90.
H
(d) H
Et
Me
Me
Br
Me
Et
Et
OH
Et
How many different stereoisomers are possible for the following compound ?
H
|
ClHC == HC — C — CH == CHCl
|
Cl
(a) 1
(b) 2
(c) 3
(d) 4
The following compounds are best described as :
( R )-PhCH(OH)CH 3 and (S)-PhCH(OH)CH 3
(a) enantiomers
(b) diastereomers
(c) not stereoisomers
(d) conformational isomers (differing by single bond rotation)
Rank the following substituent groups in order of decreasing priority according to the
Cahn-Ingold-Prelog system :
-CH(CH 3 ) 2
-CH 2Br
-CH 2CH 2Br
2
3
(a) 2 > 3 > 1
(b) 1 > 3 > 2
(c) 3 > 1 > 2
(d) 2 > 1 > 3
Compare the stabilities of the following two compounds :
A : cis-1-Ethyl-3-methylcyclohexane
B : trans-1-Ethyl-3-methylcyclohexane
(a) A is more stable
(b) A and B are of equal stability
(c) B is more stable
(d) No comparison can be made
What, if anything, can be said about the magnitude of the equilibrium constant
K for the following equilibrium ?
H
H
H3C
CH(CH3)2
H
H
CH3
91.
Br
Me
HO
OH
1
89.
H
H
H
Me
CH(CH3)2
(a) K = 1
(b) K < 1
(c) K > 1
(d) No estimate of K can be made
What is the relationship between the two structures shown ?
Cl
CH3
Cl
(a)
(b)
(c)
(d)
CH3
Constitutional isomers
Stereoisomers
Different drawing of the same conformation of the same compound
Different conformation of the same compound
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92.
Which of the following statements is true ?
(a) van der Waals’ strain in cis-1, 2-dimethylcyclopropane is the principal reason for its
decreased stability relative to the trans isomer
(b) Cyclohexane gives off more heat per CH 2 group on being burned in air than any other
cycloalkane
(c) The principal source of strain in the boat conformation of cyclohexane is angle strain
(d) The principal source of strain in the gauche conformation of butane is torsional strain
93.
Ph — CH == NO 2H ¾ isomerises
¾¾¾
¾®
3days
(x) , Isomer (x) is :
( 50 - 50%)
(a) Ph — NO — CH 2OH
(c) Ph — NH — CO 2H
(b) Ph — CH 2 — NO 2
(d) None
94.
Which of the following will not show geometrical isomerism ?
(a) CH 3 — C == CH — CH 2 — CH 3
(b) CH 3 — CH — CH == CH — CH 2 — CH 3
|
|
CH 3
CH 3
(c) CH 3 — CH == CH — CH 3
(d)CH 3 — CH 2 — CH == CH — CH 2 — CH 3
95.
The two compounds shown below are :
H
H
O
O
and
H
(a) diastereomers
96.
(b) enantiomers
H
(c) epimers
(d) regiomers
The molecular formula of diphenylmethane,
CH2
, is C 13H 12 ;
How many structural isomers are possible when one of the hydrogen is replaced by a
chlorine atom ?
(a) 6
(b) 4
(c) 8
(d) 7
97.
Correct configuration of the following molecule is :
CH3
H
OH
CH3
OH
H
(a) 2S, 3S
98.
(b) 2S, 3R
(c) 2R, 3S
Maximum enol content is in :
O
(a)
O
O
(b)
O
(c)
(d) 2R, 3R
O
H
(d) Ph
O
Ph
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99.
Which of the following will have one of the stereoisomer meso ?
(a) 2-chlorobutane
(b) 2, 3-dichlorobutane
(c) 2,3-dichloropentane
(d) 2-hydroxypropanoic acid
100.
The correct decreasing order in the enol content of following molecules is :
O
O
O
O
O
O
(II)
(I)
101.
102.
103.
104.
105.
(III)
(a) I > II > III
(b) II > I > III
(c) III > II > I
(d) II > III > I
Total number of stereoisomers of the compound 1-bromo-3-chlorocyclobutane is:
(a) 0
(b) 1
(c) 2
(d) 3
Total number of stereoisomers of the 1,3-dichlorocyclohexane is:
(a) 0
(b) 1
(c) 3
(d) 4
Total number of stereoisomers of the compound 1, 4-dichlorocyclohexane is :
(a) 0
(b) 1
(c) 2
(d) 4
Total number of stereoisomers of the compound 2-4-dichloroheptane is:
(a) 0
(b) 2
(c) 3
(d) 4
In which of the following keto form is more dominating than enol form:
O
(a)
106.
107.
(b) O
O
(c)
O
(d) all of these
O
O
Among the following compounds, which will give maximum enol content in solution :
O
O
O
O
||
||
||
||
(a) C 6 H 5 — C — CH 2 — C — C 6 H 5
(b) CH 3 — C — CH 2 — C — CH 3
O
O
||
||
(c) CH 3 — C — CH 2 — CH 2 — CH 3
(d) CH 3 — C — CH 2 — COOC 2H 5
Which of the following has unstable enol form ?
O
O
O
(a)
(b)
O
||
O
O
(c)
(d)
O
108.
Calculate enantiomeric excees of mixture containing 6g of (+) 2-butanol and 4g of
(–) -2-butanol.
(a) 10%
(b) 20%
(c) 40%
(d) 33%
109.
Which of the following pair represent pair of diastereomers ?
(a) Meso tartaric acid and (l) tartaric acid
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CO2H
H
(b) H O
CO2H
OH
HO
H
H
HO
H
CO2
CO2
CH2–CH3
(c)
H
O
CH3
O
C
and
H
CH2 – CH3
O
||
C
H
OH
H
O
CH3
OH
CH3
CH3
(d) All of these
110.
The stereochemistry of this molecule is :
H
CH3
Cl
H
(a) 1R, 3R
(b) 1R, 3S
(c) 1S, 3S
(d) 1S, 3R
111.
Pure (S)-2-butanol has a specific rotation of +13.52 degrees. A sample of 2-butanol
prepared in the lab and purified by distillation has a calculated specific rotation of +6.76
degrees. What can you conclude about the composition ?
(a) 50% (S), 50% impurity
(b) 50% (S), 50% (R)
(c) 50% (S), 50% racemic
(d) some other mixture
112.
Determine the absolute configurations of the chiral centres in the following compound.
a
O
b
Br
(a) a = R; b = S
113.
(b) a = R; b = R
(c) a = S; b = S
(d) a = S; b = R
Total number of stereoisomers possible for following compound is :
CH == CH — CH2CH3
CH == CH2
(a) 8
114.
(b) 16
(c) 32
(d) 64
Which is the correct structure of D-glyceraldehyde ?
CHO
(a) H
OH
CH2OH
H
(b) HO
CH2OH
CHO
CH2OH
(c) HO
H
(d) All of these
CHO
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115.
O
||
HO — CH 2 — CH 2 — C — H
( 3)
( 2)
(1)
Which conformer of above compound is most stable
(consider conformer across (C 2 — C 3 )
(a) Staggered
(b) Gauche
(c) Fully eclipsed
CHO
CH2 – OH
CH2 – OH
H
116.
117.
118.
119.
HO
OH
HO
H
H
H
HO
H
H
(d) Partially eclipsed
OH
CH2OH
CHO
CHO
OH
(a)
(b)
(c)
(D) & (L) Configuration of above carbohydrate is :
(a) L, L, D
(b) L, D, L
(c) L, L, L
(d) L, D, D
How many isomers have the name bromomethylcyclopentane ? (ignoring chirality)
(a) 4
(b) 5
(c) 6
(d) 7
Which of the following compound can show geometrical isomerism ?
CH3
Br
Cl
C
C == C
(a)
(b)
CH3
I
Cl
CH3
CH3
F
Et
C
C == C
(c)
(d)
CH3
CH3
Cl
Et
Which of the following structure represent meso-compound ?
H
Me
H
H
OH
Br
Me
(a) Me
(b)
O
Br
H
CH2OH
OH
(c)
H
(d)
CH2OH
H
Me
CO2H
120.
H
121.
CH3
How many representations of lactic acid are possible in Fischer projection (d & l) ?
(a) 8
(b) 12
(c) 24
(d) 36
Total number of stereoisomer formed by the given compound is :
(a) 2
OH
(b) 3
(c) 4
(d) 8
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122.
H
The number of stereoisomers formed by the given compound is :
(a) 2
(c) 4
(b) 3
(d) 5
CH3
N
O
O
N
CH3
H
123. Which of the following compound does not undergo base - catalyzed exchange
in D 2O even though it has an a-hydrogen?
O
O
(a)
(b)
O
(c)
(d) both (b) & (c)
O
OH
O
-
2O OH
¾ D¾¾¾
¾® Product
124.
long time
O
Identify the product formed in the above reaction:
OH
OD
D D
D D
O
(a)
O
(b)
D
D
O
D
D
D
O
D
OH
D D
O
(c)
(d) None of these
D
D
O
H
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99
125. In 3-methyl-2-cyclohexenone which hydrogen cannot undergo deuterium exchange when it
reacts with CH 3O Q /CH 3OD ?
O
H5
H1
H4
CH2–H2
H3
(a) H 1 , H 4
O
(b) H 4
(c) H 3 , H 2
(d) H 5 , H 3
(c) both I and III
(d) none of these
O
OH
126.
(II)
(I)
(III)
The tautomer of II is :
(a) I
(b) III
O
Ha
127.
Hb
Hg
In the enolization of the given molecule, the H-atom involved is :
(a) a-H
(b) b-H
(c) g-H
O
O
O
(d) cannot be enolized
128.
O
O
O
(II)
(I)
(III)
Among the given structure which can exhibit tautomerism ?
(a) I only
(b) II only
(c) III only
O
O
O
CH3
CH3
129.
CH3
CH3
(I)
(II)
CH3
CH3
Identify the which can exhibit tautomerism ?
(a) I only
(b) II only
(c) III only
130. CH 3 – CH = O
CH2 = CH – OH
(I)
(d) none of these
O
CH3
CH3
(III)
(d) all of these
(II)
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100
Between the two tautomers which is more stable ?
(a) I
(b) II
(c) I = II
OH
OH
O
(d) none of these
131.
(I)
(III)
(II)
Correct stability order of the given tautomers is :
(a) I > II > III
(b) III > II > I
(c) II > I > III
OH
(d) II > III > I
OH
O
132.
(I)
(III)
(II)
Correct stability order of the given tautomers is :
(a) I > II > III
(b) III > II > I
(c) II > I > III
O
O
O
OH
O¯
133.
x% ;
2+
O
(d) II > III > I
OH
y%
O
O¯
OH
z%
OH
O
The correct order of enol contents x, y, z is :
(a) x > y > z
(b) z > y > x
(c) y > x > z
O
134.
(d) x > z > y
OH
x% ;
O
O
O
O
O
y%
OH
z % ( x , y , z represent enol content)
O
The correct order of x, y, z is :
(a) x > y > z
(b) z > y > x
O
OH
(c) y > x > z
(d) x > z > y
O
O
CH3
135.
(I)
(II)
CH3
(III)
Among the given ketones, the one which does not enolize is :
(a) I
(b) II
(c) III
(d) none of these
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101
CH3
C=O
|
H
136.
D2O
ODQ
Product
The product of this reaction should be :
CD3
O
(a)
CH3
CH3
(c)
D
(b)
H
O
H
O
(d) All of these
D
O
137.
O
O
O
O
(I)
(II)
(III)
Among the given compounds, the correct order of enol content is :
(a) I > II > III
(b) III > II > I
(c) II > I > III
(d) II > III > I
O
O
O
O
138.
(I)
O
O
(II)
(III)
Among the given compounds, the correct order of enol content is :
(a) I > II > III
(b) III > II > I
(c) II > I > III
(d) II > III > I
O
O
O
139.
(I)
(II)
(III)
Among the given compounds, the correct order of enol content is :
(a) I > II > III
(b) III > II > I
(c) III > I > II
(d) II > I > III
140.
How many geometrical isomers are possible for the above compound ?
(a) 3
(b) 4
(c) 6
(d) 8
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102
141. Which of the following compound will not show geometrical isomerism across the p-bond ?
Cl
Cl
Me
C
(a)
Me
Cl
H
CH3
Cl
(c)
H
142.
Br
F
Br
F
I
I
(d)
Br
Br
l1
C=C=C
l2
H
H
H
Choose the correct relation between l1 and l 2 ?
(a) l1 = l 2
(b) l1 > l 2
(c) l1 < l 2
H
143.
(b)
l1
C=C=C=C
l2
(d) l 2 = 2l1
H
H
H
Choose the correct relation between l1 and l 2 ?
(a) l1 = l 2
(b) l1 > l 2
(c) l1 < l 2
(d) l 2 = 2l1
CH3
144.
CH3
How many geometrical isomers are possible for the above compound ?
(a) 0
(b) 2
(c) 3
(d) 4
CH3
145.
C2H5
How many geometrical isomers are possible for the above compound ?
(a) 0
(b) 2
(c) 3
(d) 4
CH3
146.
CH3
How many geometrical isomers are possible for the above compound ?
(a) 0
(b) 2
(c) 3
(d) 4
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103
CH3
147.
Br
How many geometrical isomers are possible for the above compound ?
(a) 0
(b) 2
(c) 3
(d) 4
CH3
148.
CH3
CH3
How many geometrical isomers are possible for the above compound ?
(a) 0
(b) 2
(c) 3
(d) 4
CH3
CH3
149.
How many geometrical isomers are possible for the above compound ?
(a) 0
(b) 2
(c) 3
(d) 4
l2
H
l1
CH3
CH3 CH3
C
=
C
=
C
=
C
C=C=C=C
150.
H
CH3
H
H
(II)
(I)
I and II are geometrical isomers of each other because
(a) l1 = l 2
(b) l1 > l 2
(c) l 2 > l1
(d) l1 and l 2 cannot be compared.
151. CH 2 = CH - CH = CH - CH = CH 2
How many geometrical isomers are possible for this compound ?
(a) 2
(b) 3
(c) 4
(d) 8
152. CH 3 - CH = C - C = CH - CH 3
| |
Br Cl
How many geometrical isomers are possible for this compound?
(a) 2
(b) 3
(c) 4
(d) 6
153. CH 3 - CH = C - C = CH - CH 3
| |
Br Br
How many geometrical isomers of this compound are possible ?
(a) 2
(b) 3
..
(d) 6
N – OH
R
R
N
N
|
OH
..
..
154. HO
(c) 4
R
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(a) chiral
(c) Optically active
Cl
(b) C 3 axis of symmetry
(d) All of these
Cl
Cl
Br
Br
Cl
155.
Br
(A)
(B)
Br
Relationship between above pair (A) & (B) is :
(a) Enantiomer
(b) Diastereomers
(c) Identical
(d) Structural isomer
CH3
H
H
Me
156.
O
O
NH2
(B)
(A)
NH2
(C)
(D)
From the above compound (A), (B), (C) & (D) chiral compound is :
(a) A
(b) B
(c) C
(d) D
157. Which of the following compound is achiral ?
CH2
CH2
(a)
CH2
CH2
CH2
CH2
(b)
CH2
CH2
CO2H
CO2H
CH2
CO
2H
CH2
(c)
(d)
CH2
CH2
CO2H
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105
CH2–O–CH2–CH3
CH3—(CH2)4
CH2–CH2–O–CH2–CH3
158.
O
(CH2)5–CH3
CH
CH3—(CH2)4
CH
CH3
(A)
(B)
R and S configuration of compound (A) & (B) will be :
(a) R, R
(b) R, S
(c) S, R
159. Which of following compound has center of symmetry?
Br
CH2
H
CH2
(b) CH3
(a)
CH2
CH2
(d) S, S
O
||
NH – C
CH3
H
C – NH
||
O
Br
CH3 H
Cl
(c)
H
(CH2)5–CH3
(d) All of these
Cl
CH3
160. Which mixture of structure in each beaker would rotate plane polarized light ?
CH3
H
H
HO
H
H
(a)
CH3
H
H
(&)
OH
(b)
Cl
H
OH
OH
CH3
CH3
Cl
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106
CH3
H
H
(c)
OH
OH
CH3
(d) All of these
CH3
H
H
OH
H
CH3
161. Which of following compound will rotate the plane polarized light at room
temperature?
(a)
(b)
(c)
(d)
162. Which of the following having plane of symmetry ?
H
H
H
(a)
(c)
H
H
(b)
H
H
H
H
H
H
H
(d) All of these
163. Which of following compound is achiral ?
Me
O
(a)
O
(b)
Me
O
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107
(c) H
(d) All of these
H
Br
Cl
Cl
164. Which of the following compound has plane of symmetry ?
,
R = - CH - Cl
S = - CH - Cl
|
|
CH 3
Br
S
R
(a) R
(b) S
R
R
S
(c) S
S
R
165. Which of following is E isomer ?
(a)
(d) None of these
S
R
P
(b)
O
S
P
S
S
O
O
(c)
O
C=C
O
O
O
OH
Among the given pairs, in which pair second compound has less enol content than first
compound?
O
(a)
O
O
O
O
(b)
O
(c)
167.
(d)
O
O
166.
S
O
C=C
(d) none of these
Which of the following is incorrect relation between given pairs ?
NH2
+
NH2
O
= Resonance
(a)
(b)
OH
= Tautomers
–
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108
S
(c)
168.
169.
170.
S–
H
–
O
R
+
R + O
R
= Tautomers
O
H
R
= Resonance
O+
(d)
H
O
||
Q
Ph — CH — C — H ¾ HO
¾¾® (B) ; (A) and (B) are isomer and isomerization effectively
H 2O
|
OH
( A)
carried out by trace of base (B). Identify (B).
O
O
||
||
(b) Ph — C — O — CH 3
(a) Ph — CH 2 — C — O — H
O
O
||
||
(d) H — C — CH 2 — O — Ph
(c) Ph — C — CH 2 — OH
CH 3 — CH == CH — CH == CH — CH 3 ; total number of geometrical isomer is :
(a) 2
(b) 3
(c) 4
(d) 6
Identify most stable enol form of terric acid:
O
O
H
O
H
CH3
O
O
OH
O
O
(b) O
(a) O
CH3
O
OH
O
O
O
OH
(d)O
(c) O
OH
O
171.
Which structure is most stable ?
O
O
(a)
O
OH
OH
(b)
OH
(c)
OH
O
(d)
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172.
Identify conformer of 2-methly pentane :
H
CH3
H
H
H
(a)
(b)
H
H
CH2CH3
CH3
Et
H
(c)
CH3
CH3
(d)
H
Et
H
CH3
H
H
173. The lowest energy conformer of
H
H
H
is:
CH3
(a)
CH3
H
H
H
(b)
H
(c)
(d)
Cl
174.
Cl
How many atoms will be bisect during plane of symmetry ?
(a) 2
(b) 4
(c) 6
(d) 8
175. The number of all types of isomers of chlorobutane is :
(a) 2
(b) 4
(c) 6
(d) 5
176. Which of the following pairs of compounds are not positional isomers ?
CH3
HO
OH
and
(a)
(b)
CH3
CH2OH
(c)
and
OH
OH
CH3
CH3
OCH3
(d) All of these
and
177. Which of the following pairs of compounds are functional isomers ?
and
(a)
O
O
(b)
OH
O
and
O
(c)
OH
and
O
(d)
O
and
O
O
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110
178.
The isomeric alcohol which has a chiral carbon atom is:
(a) n-butyl alcohol
(b) iso-butyl alcohol (c) sec-butyl alcohol (d) tert-butyl alcohol
179.
The pair of enantiomers among the following compound is:
H
CH3
CH3
CH3
Ph
H
Br
I
(a) I and IV
180.
181.
Br Ph
H
Ph
II
(b) II and IV
Which of the following is chiral?
(a) Cell phone
(b) Spiral staircase
Br
CH3
Br
Ph
H
III
IV
(c) II and III
(d) I and II
(c) Scissor
(d) All of these
In which of the following compound, possess plane of symmetry as well as centre of
symmetry?
CH3
Cl
CH3
Cl
(a)
(b)
(c)
(d)
CH3
Cl
182.
Which of the following compound has one of the stereoisomers as a meso compound?
(a)
183.
CH3
(b)
(c)
(d)
For the following Newman projection
H
H
H
(a)
Cl
H
H
H
(b)
Cl
H
H
Cl
Cl
H
H
H
H
H
Cl
H
Cl
(c)
Cl
Cl
H
H
H
(d)
H
Cl
Cl
H
H
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184.
Which of the following is correct for the given compound?
O
O
O
(a) It possess centre of symmetry
(c) It possess plane of symmetry
(b) It possess C 4 axis of symmetry
(d) Compound is chiral
185.
Which of the following molecules has axis of symmetry and a coaxial plane of symmetry?
O
H
H
Cl
Cl
C
H
(a) H
(b)
(c)
(d)
Cl
Cl
(e) All of these
186.
Number of diastereomer of given compound :
CH3
Cl
H
Cl
H
H
Cl
CH3
(a) 2
187.
(b) 3
(c) 4
(d) 6
Which of the structures is/are diastereomer of A ?
O
(A)
O
(1)
(2)
(3)
O
||
O
(4)
||
O
(5)
||
O
(a) 3
(b) 1 and 4
(c) 2 and 3
(d) 5
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112
188.
Identify which of the structures below are meso structures ?
O
O
(1)
O
(2)
(3)
O
O
O
||
O
O
O
||
(5)
O
190.
Find the sum of all the stereocenters that are present in below compounds :
CH3
CH3
CH3
CH3
H
H
H
H
CH3
CH3
CH3
(a) 8
H
CH3
(II)
(b) 9
(III)
(c) 10
CH3
CH3
CH3
H
(I)
193.
||
O
(c) 1,3 and 4
(d) 2 and 5
O
||
How many enol form is possible for CH 3 — CH 2 — C — CH 2 — CH 2 — CH 3 (including
stereoisomers) will be ?
(a) 2
(b) 3
(c) 4
(d) 5
H
192.
O
(b) 1,3 and 5
H
191.
||
O
O
O
(a) 1 and 3
189.
(4)
CH3
(IV)
(d) 11
A pair of stereoisomers might be classified in various ways. Which of the following statement
are true with respect to pairs of stereoisomers ?
(a) They might be configurational isomers (b) They might be diastereomers
(c) They might be constitutional isomers
(d) They might be tautomers
(e) They might be conformational isomers (f) They might be enantiomers
(g) They might be positional isomers
(a) a, b, c, e
(b) b, d, e, f, g
(c) a, b, f
(d) a, b, c, f
Ignoring specific markings, which of the following objects are chiral ?
(I) a shoe
(II) a book
(III) a pencil
(IV) a pair of shoes (consider the pair as one object)
(V) a pair of scissors
(a) I only
(b) I & V
(c) I, IV, V
(d) III, IV, V
Calculate the total number of stereoisomers when alkene having trans configuration :
O
(a) 2
(b) 3
(c) 4
(d) 8
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113
O
||
194.
-
2O / DO
¾ D¾¾¾
¾® ( B )
Prolonged
treatment
(A)
After prolonged treatment of ( A) by D 2O DO - , the difference in molecular weights of
compounds ( A) and ( B ) is :
(a) 2
(b) 3
(c) 4
(d) 8
195.
196.
Cl2
A mixture of all isomers possible from the mono-chlorination of
the structure is subjected to fractional distillation, then how many fractions will be obtained?
(a) 2
(b) 3
(c) 4
(d) 5
Br
O
O
Number of optically active isomer is/are :
hn
Br
197.
(a) 0
(b) 1
At normal temperature, X and Y
(c) 2
O
OH
X
198.
(a) resonance structures
(c) functional isomers
Two possible stereoisomers for
H
HO
199.
(d) 3
OH
Y
O
(b) tautomers
(d) positional isomers
COOH
H
are
(a) enantiomers
(b) diastereomers
(c) conformers
(d) rotamers
The configurations of the carbon atoms C 2 and C 3 in the following compound are
respectively
COOH
H
OH
H
OH
CHO
(a) R, R
200.
(b) S, S
The compound that is chiral is
(a) 3-methyl-3-hexene
(c) 2-phenylpentane
(c) R, S
(d) S, R
(b) 4-chloro-1-methycyclohexane
(d) 1, 3-disopropylbenzene
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114
201. Number of optically active tartaric acid is/are possible :
(a) 1
(b) 2
(c) 3
(d) 4
Br
O
O
202.
Number of optically active isomer is/are :
Br
(a) 0
(b) 1
(c) 2
203. Correct relationship b/w pair of compounds.
(1)
and
(2)
and
(d) 3
and
(3)
(a)
(b)
(c)
(d)
1-Conformer ; 2-Conformer ; 3-Conformer
1-Conformer ; 2-Stereoisomers (GI) ; 3-Stereoisomers (GI)
1-Conformer ; 2-Stereoisomers (GI) ; 3-Conformer
1-Stereoisomerism (GI) ; 2-Stereoisomerism (GI) ; 3-Conformer
CH3
204. Number of diastereomers possible for
CH–CH3
(a) 1
BrH2C
205.
H
(b) 2
CH2–Br
C
C
H
Br
Br
H3C
H
H
C
Br
Sum X + Y = ?
(a) 1
C
H
(c) 4
(d) 0
No. of enantiomer = X
No. of diastereomers = Y
CH3
(b) 3
(c) 4
(d) 0
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115
ANSWERS – LEVEL 1
1.
(b)
2.
(c)
3.
(b)
4.
(c)
5.
(a)
6.
(b)
7.
(c)
8.
(d)
9.
(c)
10.
(d)
11.
(b)
12.
(c)
13.
(a)
14.
(b)
15.
(b)
16.
(d)
17.
(c)
18.
(a)
19.
(b)
20.
(b)
21.
(d)
22.
(b)
23.
(c)
24.
(d)
25.
(a)
26.
(b)
27.
(d)
28.
(b)
29.
(a)
30.
(c)
31.
(c)
32.
(a)
33.
(b)
34.
(c)
35.
(c)
36.
(d)
37.
(c)
38.
(d)
39.
(b)
40.
(a)
41.
(a)
42.
(d)
43.
(a)
44.
(d)
45.
(a)
46.
(b)
47.
(c)
48.
(b)
49.
(c)
50.
(c)
51.
(d)
52.
(d)
53.
(e)
54.
(a)
55.
(d)
56.
(c)
57.
(d)
58.
(b)
59.
(a)
60.
(a)
61.
(c)
62.
(d)
63.
(e)
64.
(d)
65.
(b)
66.
(b)
67.
(d)
68.
(d)
69.
(d)
70.
(d)
71.
(d)
72.
(a)
73.
(b)
74.
(a)
75.
(b)
76.
(b)
77.
(a)
78.
(b)
79.
(c)
80.
(b)
81.
(d)
82.
(a)
83.
(b)
84.
(a)
85.
(a)
86.
(d)
87.
(a)
88.
(d)
89.
(a)
90.
(b)
91.
(a)
92.
(a)
93.
(b)
94.
(a)
95.
(b)
96.
(b)
97.
(a)
98.
(d)
99.
(b)
100. (a)
101.
(c)
102.
(c)
103.
(c)
104. (d)
105. (d)
106. (a)
107.
(c)
108. (b)
109. (d)
110. (a)
111.
(c)
112.
(c)
113. (a)
114. (d)
115. (b)
116. (b)
117.
118. (d)
119. (b)
120.
(c)
121. (a)
122. (b)
123. (d)
124. (b)
125. (b)
126.
127.
(c)
128. (b)
129. (d)
130. (a)
131.
(c)
132. (d)
133. (d)
134. (d)
135. (b)
136. (b)
137.
(c)
138. (a)
139. (d)
140. (b)
141. (b)
142. (a)
143.
144. (b)
145. (b)
146. (b)
147. (b)
148. (a)
149. (b)
150.
(c)
151. (a)
152.
153. (b)
154. (d)
155.
(c)
156. (a)
157.
158. (d)
159. (d)
160. (d)
161. (b)
162. (d)
163. (d)
164. (d)
165. (d)
166.
(c)
167. (d)
168.
(c)
169. (b)
170.
(c)
171.
(c)
172. (d)
173. (b)
174.
(c)
175. (d)
176.
(c)
177. (b)
178.
(c)
179.
(c)
180. (d)
181. (d)
182. (b)
183. (b)
184.
(c)
185.
(e)
186. (b)
187. (b)
188. (a)
189.
190.
191.
192. (b)
193.
(c)
194.
195. (b)
196. (a)
197. (b)
203.
204. (d)
205. (d)
201. (b)
(c)
202. (a)
(c)
(c)
(c)
(c)
(c)
(c)
198. (a)
(c)
(c)
199. (a)
200.
(c)
(c)
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116
Level - 2
1.
Match the Column (I) and (II).
(a)
Column (I)
Column (II)
Reaction
Stereoisomers
CH 3 — CH == CH — CH == N — OH
(b)
2.
(p)
2
(q)
4
(c)
CH 3 — CH == CH — CH == CH — CH == CH — CH 3
(r)
6
(d)
CH 3 — CH == CH — CH == CH — CH == CH - Ph
(s)
8
Match the Column (I) and (II).
R
Keq
R
Column (I)
Column (II)
Group
Equilibrium Constant
(a)
R == — H
(p)
38
(b)
R == — CH 3
(q)
23
(c)
R == — Et
(r)
18
(d)
R == — CH — CH 3
\
CH 3
(s)
1
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117
3.
Match the Column (I) and (II). (Matrix)
Column (I)
Column (II)
Molecule
Nature
H
CO2CH2CH2OH
(a)
(p)
Chiral
(q)
Achiral
(r)
Meso
(s)
Compound containing even
number of chiral centers
CO2H
H
H
H
CO2CH2CH2O2C
(b)
H
CO2CH2CH2O2C
OH H
(c)
CO2H
H
H
(d)
HO
H
CO2H
OH
CO2H
CO2H OH
H
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118
4.
Match the Column (I) and (II). (Matrix)
Column (I)
Column (II)
Compound
Isomerism
CH3
H
(a)
H
Et
CH3
Et
(b)
H
(p)
Geometrical isomerism
(q)
Optical isomerism
(r)
Compound containing plane of symmetry
(s)
Compound containing center of symmetry
H
D
CH3
(c)
Et
H
H
H
CH3
CH3
(d)
H
H
CH3
H
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119
5.
Match the Column (I) and (II).
Column (I)
Column (II)
Molecules
Relationship
Cl
(a)
Cl
and
CH3
Cl
(b)
Cl
and
CH3
Cl
(c)
CH3
and
(q)
Enantiomer
(r)
Diastereomer
(s)
Structural Isomerism
Cl
Cl
and
CH3
(d)
Identical
CH3
CH3
Cl
(p)
CH3
CH3
6.
Match the Column (I) and (II). (Matrix)
Column (I)
Column (II)
Compound
Nature
CH3 Br
(a)
CH3
HO
(d)
(p)
cis-compound
CH3
(q)
trans-compound
(r)
Optically active
(s)
Optically inactive
OH CH3
CH3
CH3 HO
(c)
CH3
Br
Br
(b)
OH CH3
Br
CH3
CH3
CH3
CH3
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120
7.
Match the Column (I) and (II). (Matrix)
Column (I)
Column (II)
Molecule
Property
H
H
C == C == C
(a)
Cl
(p)
Chiral centers containing compound
(q)
Presence of stereocenter
(r)
Optically active compound
(s)
Compound containing plane of symmetry
Cl
H
(b)
CH 3
CH3
H
Cl
Br
(c)
F
I
CH3
(d)
OH
C == N
Et
8.
Match the Column (I) and (II). (Matrix)
Column (I)
Column (II)
Molecule
Property
F
H
C == C == C == C
(a)
H
F
Polar molecule
(q)
Optically active
(r)
Optically inactive
(s)
Plane of symmetry
H
C == C == C
(b)
H
(c)
(p)
F
F
F
F
H
H
F
H
H
(d)
H
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121
9.
Match the Column (I) and (II). (Matrix)
Column (I)
Column (II)
Molecule
Property
Me
H
(a)
Me
Me
Meso compound
(q)
Achiral
(r)
Chiral compound
H
(b)
Me
(p)
H
H
(c)
H
Me
Me
(d)
H
Me
Me
H
(s) Compound will show geometrical isomerism
H
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122
10.
Match the Column (I) and (II).
Column (I)
Column (II)
Modified Newmann Projection
Conformers
CH3CH3
(a)
H H
(p)
Fully eclipsed
(q)
Partially eclipsed
(r)
Gauche
(s)
Staggered
H H
H CH3
(b)
H H
CH3 H
CH3
H
H
(c)
H
H
CH3
CH3
H
CH3
(d)
H
H
H
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123
11.
Match the Column (I) and (II).
Column (I)
Column (II)
Newmann Projection
Name of the Compound
CH3
H
CH3
(a)
(p)
3-methyl pentane
(q)
n-butane
(r)
Methyl-cyclopentane
(s)
1,2,4-trimethyl cyclohexane
H
H
CH3
CH3
CH3
(b)
H
H
H
H
CH3
H
(c)
H
H
CH3
H
H
H
H
H
(d)
CH3
CH3
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124
12.
Match the Column (I) and (II). (Matrix)
Column (I)
Column (II)
Molecule
Property
(a)
(p)
Rotates plane polarized light
(q)
Cannot rotate plane polarized light
(r)
Plane of symmetry
(s)
Centre of symmetry
Cl
(b)
Br
Cl
Br
(c)
AsMe3
(d)
CH3
I
C == C == C
CH3
13.
Cl
Match the Column (I) and (II).
(a)
Column (I)
Column (II)
Molecule
Stereocenters
CH 3 — CH == CH — CH— CH 3
|
(p)
1
(q)
2
(c)
O
||
Ph — S — CH == CH — CH — CH 3
|
CH 3
(r)
3
(d)
Ph — CH — Et
|
Cl
(s)
4
(b)
Br
H — C ºº C — CH == CH — CH— CH— CH 3
|
Br
|
Br
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125
14.
Match the Column (I) and (II).
Column (I)
Column (II)
Molecule
Stereoisomers
H
C
COMe
C
(a)
(p)
2
(q)
0
(r)
4
H
C
COMe
C
(b)
H
C
COMe
C
(c)
H
C
C
(d)
COMe
(s)
8
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15.
Match the Column (I) and (II). (Matrix)
Column (I)
Column (II)
Molecule
Property
O
C — Me
Me
(a)
Me
(p)
Meso Compound
(q)
Compound having even no. of
chiral centres
(r)
Optically active compound
(s)
Compound having odd no. of
chiral centres.
O
Me2N
OH
Me
C ºº C — Me
(b)
O
O
H
(c)
O
H
O
N
H
COOH
(d)
H
H
OH
OH
COOH
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16.
Match the Column (I), (II) and (III). (Matrix)
Column (I)
Column (II)
Column (III)
Property
Molecule
No. of Chiral Center
Optically active
(w)
0
(x)
1
(r) Plane of symmetry (y)
2
Centre of
symmetry
3
CHDCl
CH3
C == C
(a)
H
(p)
H
CH3
(b)
(q) Optically inactive
CH3
Os
|
CH 3 — Å N — HCl s
|
Et
(c)
H
H
(d)
(s)
Cl
Cl
(z)
17.
H
CH3
CH3
(a) H3C
O
(b)
(c)
O
H
(d)
H
(e)
C == C == C
H
H
C == C == C
H
H
(h)
Br
H
CH3
H
CH3
H
(f)
H
OH
CH3
Br
(g)
CH3
CH3
CH3
H
CH3
OH
CH3
CH3
OH
From the above compounds select :
(A) two of which are chiral and contain chiral centre :
(B) two of which are achiral and contains chiral centre :
(C) two of which are chiral and does not contain chiral centre :
(D) two of which are achiral and does not contain chiral centre :
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18. Comprehension
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
(P)
(Q)
(R)
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
(S)
(T)
(U)
Consider the given structures and answer A, B & C.
A.
Which of the compound is optically active ?
(a) P
B.
(b) R
(d) T
(c) T
(d) U
Which of the isomer is most stable ?
(a) R
19.
(c) S
(b) S
Identify relationship between following pairs :
OH
CO2H
H
H
CO2H
OH
(a)
Cl
(b)
Cl
OH
CO2H
HO
Cl
CO2H
F
Br
Br
H
H
Cl
F
H
OH OH
(c)
CH3
F
(d)
F
H3C
H
CH3
H
F
CH3
C—C
F
H
If they are enantiomer answer will be 1, if they are diastereomers answer will be 2, if they are
constitutional isomers answer will be 3 and if they are identical present 4 as the answer. Sum
of answer of each part a + b + c + d is : . . . . . . . .
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20.
In each of the following three questions a hydrocarbon is named. For each select from among
the sixteen conformational structures (a through p) all structures that represent possible
conformers of that compound. Write letters (a through p), corresponding to your selections,
in each answer box.
A.
2-methylbutane
B.
2,3-dimethylpentane
C. 1-ethyl-1, 3-dimethyl cyclohexane
H
C H3
C H3
H
(a)
C H3
C 2H5
H3C
(e)
CH3
H
H
H
H
C H3
C H3
(g)
(h)
C 2H5
H
C H3
H
(j)
C2H5
H
H
H
CH3
H
C2H5
(p)
CH3
H
C2H5
(m)
H
C H3
H
H3C
CH3
H
CH3
H
H
H
C2H5
C 2H5
H
(f)
H
CH3
C 2H5
C H3
H3C
CH3
C 2H5
(i)
CH3
C H3
H3C
C 2H5
(k) H C
3
C H3
C 2H5
CH3
(l)
CH3
C 2H5
CH3
(n)
C H3
C 2H5
(o) H3C
C 2H5
C H3
H
H
H3C
H3C
C H3
C H3
H
H
C H3
CH3
H
H3C
(c)
H
H
H3C
CH3
CH3
(b)
H
H
(d)
H
H
H
CH3
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21.
Examine structures a through j, shown below, with respect to their symmetry or lack of it.
Assume that the five-membered rings and the ring in compound g are planar. The
wedge-hatched bonds in b, c, d & e designate specific configurations. Also, for the acyclic
compounds assume stable anti conformations. Answer each of the following questions by
writing letters (a through j), corresponding to your selections, in each answer box. If there is
no structure that fits the description enter an x in the answer box.
A.
Which structures are chiral ?
B.
Which structures have a plane of symmetry ?
C.
Which structures have a center of symmetry ?
H
Br
OH
Br
(a)
(b)
Br
(c)
Cl
OH
Br
Br
Br
(d)
Br
(e)
(f)
H
O
(g)
(j)
22.
(h)
C 2 H 5 CHCl 2
(i)
C 2 H 5 CHClC 2 H 5
C 2 H 5 CHClCH 3
(i) 1,2-dichlorocyclopropane = w
(ii) 1,3-dimethyl-cyclobutane = x
(iii) 2-bromo-3-chlorobutane = y
(iv)1,3-dimethyl cyclohexane = z
Calculate total number of stereoisomer of the above compounds.
Sum of w + x + y + z = KK
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23.
Examine the following formulas and select those pairs that satisfy the following conditions :
Be sure to write two letters (and only two) in each answer box, unless you select f. In the
second and third parts more than one answer is possible.
C2H5
H
C H3
H
(a)
(b)
C H3
C 2H5
H
H3C
H
H
H
H3C
H
(c)
H
C H3
H3C
CH3
C H3
C H3
H
H
(d)
C2H5
H3C
24.
C H3
H
H3C
H
CH3
H
(e)
(f) No formulas meet the
designated condition
C H3
A.
Which are identical in all respects?
B.
Which are conformational isomers?
C.
Which are constitutional isomers?
Examine the following formulas and select those pairs that satisfy the following conditions :
Be sure to write two letters (and only two) in each answer box. In the second and fourth parts
more than one answer is possible.
H
Br
(a)
H
Br
(b)
Br
Br
H
H
(c)
Br
H
H
Br
Br
H
Br
(d)
H
Br
(e)
Br
H
H
Br
A.
Which are identical in all respects?
B.
Which are configuration isomers?
C.
Which are conformational isomers?
(f)
Br
H
H
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25.
Consider the following statements regarding the given projection (True or False).
CH2Cl
CH2Cl
H
Cl
(W)
Br
H
CH3
CH3
CH3 H
Br
(Y)
26.
H
CH2Cl
Cl
H
Cl
(Z)
Cl
H
H
Cl
Cl
H
(X)
CH2Cl
CH3
(a)
W and Y are diastereomers
(b)
Z is the projection of X
(c)
W, X, Y and Z are optically active
(d)
Y and Z are isomer
Examine the following structural formulas and select those that are chiral.
NH2
OH
(a)
CN
O
(b)
(c)
CO2H
CO2H
(d)
(e)
H
H
CN
OH
OH
(f)
H
HO
OH
CH3
OH
CH2 – CO2H
CH2 – CO2H
OH
(g)
SO3H
CH3
NO2
(h)
(i)
NO2
SO3H
CH3
CH3
C=C=C
H
H
CH3
(j)
Cl
Cl
H
H
CH3
Write your choice here
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27.
The configuration of eight compounds, a through h are shown below, using various kind of
stereo representations. To answer the question given below, write (a through h) indicating
your choice.
O
H
(a) CH3CH2 — C
OH
CH3
CºN
C—H
(b)
(c) HC º C — C
H
CO2H
CH3
— CH2 — C
(d)
Br
(e)
(f)
CH3 O
O
CH3
H
CH3
H
OH
H
OH
H
OH
CH3
CH3
(g)
(h)
CH2
CH(CH3)2
C2H5
O
H
C
CH3
CH3
O
A. Which of these configuration are achiral?
B. Which configuration has no stereogenic center?
C. Which configuration has more than one stereogenic center?
D. Which of these configuration are meso compound?
28.
The structural formula of ten compounds, (I) through (X) are drawn below, you may select
any one of these structure.
Answer the following question about that compound.
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CH3
HO
CH3
I
II
CH3
III
CH3
CH3
CH3
CH3
CH3
IV
V
VI
Et
CH3
CH3
OH
CH3
CH3
CH3
VII
VIII
IX
CH3
CH3
OH
OH
OH
OH
OH
CH3
X
CH3
OH
A.
B.
How many chiral centre are present in this compound ?
(a) 0
(b) 1
(c) 2
(e) 4
(f) 5
(d) 3
Is this compound chiral or achiral ?
(a) Chiral
(b) Achiral
C.
What symmetry element are present in this compound ?
(a) None
(b) Plane of symmetry
(c) Center of symmetry
29. The structure of one of the enantiomers of the amino acid cysteine is shown below.
1
H2N
3
COOH
H4 R
CH2SH
2
Classify this structure as :
(a) R or S
(b) D or L
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30. Identify the following double bonds either E, Z or None (N) in the compounds given below
either.
A.
1
3
4
2
O
H3CO
5
H3CO
6
7
O
B. (a) Bongkrekic acid is a toxic compound produced by Pseudomonas cocovenenans, and
isolated from a mold that rows on bongkrek, a fermented Indonesian coconut dish. (a) Label
each double bond as E, Z or neither (N).
COOH
COOH
2
COOH
3
4
OCH3
Bongkrekic acid
6
5
1
(b) How many total stereoisomers (including all types) are possible for bongkrekic acid ?
..........
(c) How many sites of unsaturation are present in bongkrekic acid ? .................
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31. Designate the following double bonds as E, Z or none (N) configuration in the boxes
provided below.
O
NH2
O
1
2
3
32. The following compounds may exist as two or more stereoisomers. These may be classified
as enantiomer pairs or meso compounds.
C6H5
C6H5
CO2H
(a)
CO2H
(b)
C6H5
HO2C
C6H5
truxillic acid
CO2H
truxinic acid
Cl Cl
CO2H
(c)
(d)
Cl
Cl
Cl
(e) C(CH 3 CHCl) 4
Cl
Cl
CHCO2H
Cl
CO2H
(f)
Cl
(g)
Cl
C = CHCO2H
(h)
Cl
Answer the following question about the above structure.
(A) Total number of stereoisomers :
(B) Number of enantiomeric pairs :
(C) Number of meso compounds :
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33. Identify axis of symmetry in the given compound.
Me
Et
Cl
Cl
Et
Me
Et
(1)
(2)
Me
Cl
Me
Et
Me
Et
O
N
O
O
O
O
(3)
Et
Cl
O
O
N
O
Me
Cl
Cl
(4)
Cl
O
N
Me
Br
Cl
Br
(5)
(6)
Cl
Br
Cl
N
N
Me3C
CMe3
N
CMe3
O
O
O
N
N
(7)
(8)
O
O
O
O
N
N
O
O
O
Cl
H
(9)
(10)
Cl
H
Cl
H
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Cl
Cl
O
(11)
(12)
O
(13)
34. For each of the following pharmaceutical compounds, identify all stereogenic (i.e., all
asymmetric carbon atoms) and label the configuration of each as being either (R) or (S).
O
OH
HO
O
HO
O
O
erythromycin
H
O
O
O
(1)
N(CH3)2
HO
OH
NCH3
(2)
OCH3
O
HO
morphine
F
O
S
OH
O
NH2
(3)
H
N
N
H H
O
O
OH
HO
H
(4)
F
HO
amoxicillin
O
H
flonase
F
HO
O
(5)
O
O
O
O
O
OSO2NH2
O
(6)
O
O
topomax
zocor
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35. Find relationship between given pair :
Identical Enantiomer Diastereomer
Constitutional
Isomer
1.
CO2H
CO2H
2.
OH
OH
3.
OH
OH
Et
CH3
OH HO
OH HO
H
H
4.
Et
H
H
CH3
H
CH3 CH3
CH3
H
H
5.
6.
CH3
H
CH3
CH3
CH3
CH3
H
H
H
H
C
H
C
CH3
CH3
H
7.
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8.
CH3
H
H
CH3
CH3
H
H
CH3
9.
10.
36. Comprehension
Structural formula of compound ( A) is following:
HO2C
CO2H
A.
The correct statement(s) about the compound ( A) is/are:
(a) The total number of stereoisomers possible for ( A) is 3
(b) The total number of mesoisomer possible for ( A) is 1
(c) The total number of pair of enantiomer possible for ( A) is 1
(d) All of these
B.
Number of plane of symmetry in cis-form of compound ( A) is:
(a) 0
(b) 1
37. Match the column. (Matrix)
(c) 2
(d) 3
Column (I)
Column (II)
No. of Carbon
No. of structural isomer
(a)
C 4H10
(p)
2
(b)
C 5H12
(q)
3
(c)
C 6H14
(r)
5
(d)
C7H16
(s)
9
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38.
Match the column. (Matrix)
Column (I)
Column (II)
Compound
% of enol content
(a)
(p)
100 %
(q)
76 %
(c)
O
O
||
||
CH 3 - C - CH 2 - C - CH 3
(r)
8%
(d)
O
O
||
||
CH 3 - C - CH 2 - C - O - Et
(s)
Keto-Enol is not possible
O
O
O
(b)
O
39. Draw a most stable conformation (N – C) bond in the following compound.
H
H
..
N—C = C
H
H
H
40.
Find total number of stereoisomers for each compound given below :
O
||
(1) Ph - S - CH = CH - CH 2 - CH = C = C = CH - CH = CH - CH 3
CH –
C H= I
CH3
Cl
(2)
H
Br
(3)
NO2 Cl
CH3
N–OH
(4) Ph – CH – CH – NH – CH3
|
|
OH CH3
O
O
||
||
(6) H – O – C – CH – CH – C – H
|
|
OH OH
(5)
O
N–H
O
(7)
OH
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41.
Cl
(8)
(9)
(10) CH3 – CH = CH – CH – CH3
|
Br
(11)
CH – CH = CH – CH 3
H
CH – CH 3
Find the total number of stereoisomer for each compound :
(1)
b ¾® a
b
a
(2)
a
b
¾® b
a
(3)
a
a
¾® c
(4)
a
b
a
a
(5)
¾® e
b
¾® d
(6)
d
a
a
¾® f
42. Match the column :
Column (I)
Column (II)
Pair
O
||
C—O
(a)
CH3
(b)
Isomeric Relationship
CH3
O
||
C—O
O
||
CH 3 - CH 2 - CH 2 - C - OH , CH 3 - CH - CH 3
|
CO 2H
(p)
Chain
(q)
Positional
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,
(c)
NO2
(r)
Functional
(s)
Metamers
NO2
CH2OH
OH
(d)
CH3
43. Find sum of stereoisomer of following compound.
Number of stereoisomers
O
CO2H
(a)
¾¾®
(a)
¾¾®
(b)
HO
OH
OH
CH3
(b)
HO
(c) HOCH2–CH–CH–CH–CH–CH2–CH–CH–CH–CH–CH2–OH ¾¾®(c)
OH
CH2–OH
OH
O
O
(d) HO
OH
OH
¾¾®
(d)
OH
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O
O
H
OH
44.
H
HO
OH
1
Prostaglandin E1
Prostaglandin E 1 1 is a compound produced by the body to regulate a variety of processes
including blood clotting, fever, pain and inflammation.
A.
Which of the following functional groups is not contained in 1 ?
(a) A ketone
(b) An alcohol
(c) A carboxylic acid (d) An alkene
(e) A nitrile
B.
How many asymmetric (stereogenic) centres are present in compound 1?
(a) 3
(b) 4
(c) 5
(d) 6
C.
How many sp 2 hybridised carbon atoms are present in compound 1 ?
(a) 1
D.
(b) 2
(c) 3
(d) 4
What is the geometric configuration about the double bond in compound 1?
(a) E
(b) Z
H3C
OH
H
H
45.
H
H
HO
Ethynylestradiol (1)
The synthetic steroid ethynylestradiol (1) is a compound used in the birth control pill.
A.
How many sp 3 hybridised carbon atoms are present in compound (1)?
(a) 8
B.
(c) 10
(d) 11 (e) 12
How many sp hybridised carbon atoms are present in compound (1) ?
(a) 4
C.
(b) 9
2
(b) 5
(c) 6
(d) 7
How many sp hybridised carbon atoms are present in compound (1) ?
(a) 2
(b) 4
(c) 6
(d) 8
(e) 8
(e) 10
D.
Which of the following functional group is contained in compound (1) ?
(a) A ketone
(b) An alcohol
(c) A carboxylic acid (d) An ester
E.
How many asymmetric (stereogenic) centres are present in compound (1) ?
(a) 2
(b) 3
(c) 4
(d) 5
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46.
Match the column.
Column (I)
Column (II)
(a) C 2-axis of symmetry
(p)
(b) C 3-axis of symmetry
(q)
H3C
(c) Plane of symmetry
CH3
(r)
H3C
(d) Centre of symmetry
(s)
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H3C
(t)
CH3
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Subjective Problems
1. Number of chiral isomers are:
Cl
Cl
(a)
Cl
H
H
(b)
H
H
Cl
Br
H
(c)
D
Br
H
Cl
(i)
H
H
Cl
H
(f) Cl
H
H
H
CH3
H
(e)
H
Cl
(d)
H
H
Cl
Cl
Cl
H
H
H
H
(g)
Consider only a
conformation with Me
group perpendicular
to the aromatic ring
CH3
(j)
(h)
CH3
CH3
CH3
(k)
Cl
O
CH2—OH
Cl
2.
Cl
Number of stereoisomer are
H
C
3.
(i)
CH3
H
(ii)
2
(D)
¾¾®
Ni
(Major)
CH3
(C)
Sum of number of stereoisomer (C) Degree of unsaturations in (D).
4. How many 5 membered parent chain alkane are possible for C 7 H 16 ?
5. Theoretical possible geometrical isomer of
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6. Total number of possible structural isomers of C 5H 11Br.
7. Total number of plane of symmetry present in given compound is
Cl
Cl
Cl
Cl
8. Total number of isomers for C 4H 6Br 2 containing cyclobutane ring are ( including
stereoisomer) ?
9. Total number of structural isomers of C 9H 18 containing cyclohexane ring.
10. How many structural isomer are possible for C 4H 10O (only alcohol).
11. Number of structural isomer of C 6H 14 is .
CH2—Cl
12. (a)
¾¾® (x) ( Number of plane of symmetry)
CH2—Cl
(b)
Cl
Cl
¾¾® (y) ( Number of mesoisomer of 1, 2-dichlorocyclopentane)
Sum of (x+y=?)
13. Find out the total number of stereocentre in the given compound.
CH3—CH ==CH—CH—CH—CH 3
Br Cl
14. Find out the total number of stereoisomers of the given following compound.
Cl
Cl—CH ==CH—C—CH==CH—Cl
H
15. Find the total number of isomers of C 7 H 14 (only 5-membered ring).
16. x = number of compounds which undergoes Tautomerisation to form an Aromatic product.
O
O
(a)
(b)
O
(c)
O
(d)
N
O
H
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O
O
O
O
(e)
(f)
(g)
(h)
N—O—H
17.
If molecule is pyramidal, X stereoisomers are possible for :
C abed
find the value of X.
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ANSWERS — LEVEL 2
1.
a – q; b – p; c – r; d – s
2. a – s; b – r; c – q; d – p
3.
a – p, s; b – q, r, s; c – q, r, s; d – p, s
4. a – p, q; b – p, q; c – p, q; d – p, r
5.
a – r; b – r; c – p; d – s
6. a – p, r; b – q, s; c – q, r; d – p, s
7.
a – q, r; b – q, s; c – p, q, r; d – q, s
8. a – r, s; b – p, q; c – r, s; d – p, r, s
9.
a – q; b – q, s; c – p, q, s; d – q, s
10. a – p; b – q; c – s; d – r
11.
a – p; b – q; c – r; d – s
12. a – q, r; b – p; c – p; d – q, r
13.
a – r; b – s; c – r; d –p
14. a – s; b – r; c – q; d – p
15.
a – q, r; b – r, s; c – q, r; d – p, q
16.
(a – p – x); (b – q, r – y); (c – p – x); (d – q, r – w)
17.
A – b,h; B – a, g; C – c, e; D – d, f
18.
A – d; B – a
19.
a + b + c + d = 13
20.
A – b, d, e; B – a, c, f, h; C – i, k, p
21.
A – e, f, j; B – a, c, d, g, h, i, b; C – None
22.
w + x + y + z = 12
23.
A – (c & e), (b & d); B – (a & b) or (a & d); C – (a & c) or (a & e), (b & c), (b & e), (c & d) and
(d & e)
24.
A – (a & c) (b & f); B – (a & d) or (c & d), (a & e) (c & d); C – (d & e)
25.
a – True; b – True; c – True; d – False
26.
b, e, f, g, h, i
27.
A – d, h; B – d; C – f, h; D – h
28.
Compound
A
B
C
I
c
a
a
II
c
b
b
III
c
a
a
IV
c
b
b
V
c
a
a
VI
c
a
a
VII
c
a
a
VIII
e
b
b
e
a
e
b
(b) L
a
b
IX
X
29. (a) R
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151
30A.
B.
31.
32.
1 – N; 2 – Z; 3 – E; 4 – Z; 5 – Z; 6 – E; 7 – N
(a) 1 – Z; 2 – E; 3 – E; 4 – Z; 5 – Z; 6 – E
(b) 2 9
(c) 10
1 – Z; 2 – N; 3 – E
(a) A – 10, B – 4, C – 2
(b) A – 5, B – 0, C – 5
(c) A – 4, B – 2, C – 0
(d) A – 2, B – 1, C – 0
(e) A – 5, B – 2, C – 1
(f) A – 4, B – 1, C – 2
(g) A – 4, B – 2, C – 0
(h) A – 4, B – 1, C – 2
Me
Cl
Et
C2
C3
Et
Cl
Me
Et
33. (1) Me
(2)
Cl
Cl
Me
Et
Et
Me
O
N
O
O
Et
O
(3)
O
O
C3
O
N
Cl
O
Cl
(4)
O
N
Cl
Me (C )
3
C3
Br
Cl
Br
N
Me3C
(5)
(6)
Cl
Br
C3
Cl
(7) C 3 axis, C 2 axis
N
CMe3
N
CMe3
(8) C 3 -axis
O
axis
(9) C3
Cl
(11)
(10)
Cl
(12) C 2 -axis
(13) C 2 -axis
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O
(R)
(R)
OH
(R)
HO
OH
(S)
(R)
(R)
O
O
34. (1)
(R)
(R)
(S)
(S)
O
(S)
(S)
O
(2)
O
(R)
OCH3
HO
(R)
(S)
(R)
NCH3
(R)
(S)
morphine
(S)
(S)
H
O
(R)
O
(S)
erythromycin
HO
N(CH3)2
HO
(R)
F
O
S
OH
O
NH2
(R)
(3)
(R)
N
H
N
O
(R)
(R)
(S) (S)
(S)
(S)
HO
amoxicillin
H
(R)
(4)
H H
O
OH
HO
O
F
(S)
(S)
(S)
(R)
H
flonase
F
HO
O
(R)
O
(R)
(5)
O
(S)
(R)
(S)
O
O
O
OSO2NH2
(R)
O
O
(6)
(S)
O
(S)
(S)
(R)
topomax
zocor
35.
Identical Enantiomer
(1)
×
CO2H
(2)
Diastereomer Constitutional
Isomer
×
×
CO2H
×
×
×
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OH
OH
(3)
OH
OH HO
OH HO
H
H
×
×
×
×
×
×
×
×
×
×
×
×
×
×
×
×
×
×
×
×
Et
CH3
(4)
×
OH
Et
H
H
CH3
H
CH3 CH3
H
(5)
CH3
CH3
(6)
H
H
CH3
H
H
CH3
CH3
CH3
H
H
C
H
C
CH3
CH3
H
(7)
(8)
CH3
H
H
CH3
(9)
CH3
(10)
H
H
CH3
×
×
×
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36. (A) - (d)
(B) - (b)
37. a – p; b – q; c – r; d – s
38. a – s; b – p; c – q; d – r
39. H
H
H
H
N
(Resonance)
H
H
N
H
p-(vacant-p-orbital)
40. (1) 16
(2) 4
(3) 16
(4) 4
(5) 4
(6) 4
(11) 2
(7) 4
(8) 3
(9) 4
(10) 4
41.
42.
43.
44.
45.
46.
a – 2, b – 4, c – 3, d – 4, e – 8,
a – s; b – p; c – q; d – r
a – 2 5, b – 2 5, c – 27 + 2 3,
d – 29
A – e; B – b; C – d; D – a
A – e; B – c; C – a; D – b; E – d
a – p, q, s, t; b – p, r; c – p, q, r, s, t;
f–2
d–p
Subjective Problems
1. 3 (c, f, h)
8. 6
9. 12
16. 4 (a, b, c, h)
2. 64
10. 4
3. 5
4. 5
5. 2
6. 8.
7. 3
11. 5
12. 4
13. 4
14. 4
15. 8
17. 6
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155
3
GRIGNARD REAGENT
Level - 1
1.
What is the major product of the following reaction ?
O
CH MgI
Et 2O
H OÅ
3
3
¾ ¾¾
¾® ¾ ¾¾
¾®
CH3
OH
(a)
(b)
CH2 – CH3
CH2 – OH
O
(c)
OH
CH3
(d)
CH3
CH3
C – OCH3
2.
CH3
PhMgBr
¾ ¾¾¾® (P). Product (P) is :
O
(1 equivalent)
CH2 – COCH3
O
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CH3 O
CH3 O
C — Ph
(a)
C — Ph
(b)
CH2 — COCH3
CH2 — COCH 3
O
O
CH3
(c)
CH3
C — Ph
CH3
O
CH2 — C — Ph
||
O
O
SH
O
C – Cl
HO
3.
(d)
O
CH2 — COCH 3
C — OCH3
Reaction- 1 ;
SH
1. x CH3MgBr
OH
2. H3OÅ
OH
| CH3
C
CH3
CH3
C
| CH3
OH
C – Cl
O
OH
O
C — O — Et
CH3 — C — CH
3
1. y CH3MgBr
Reaction- 2 ;
2. H3OÅ
CH3
CH2 — Cl
What is the ratio of (x y) in above problem ?
(a) 1.5
4.
(b) 2
(c) 2.5
(d) 3
In which of the following reaction 2° alcohol is obtained as a product ?
(1) CH MgBr
3
¾ ¾¾¾¾
¾®
(a)
(b) CH3
(2) H 2O
O
(1)
MgCl
O
(2) H 2O
O
(c)
5.
(1) CH MgBr
3
¾ ¾¾¾¾
¾®
(2) H 2O
(d) Both (a) and (b)
What product would you expect to obtain from Grignard reaction when an excess of
phenylmagnesium bromide reacts with dimethyl carbonate CH 3 OCOOCH 3 ?
OH
OH
O
OH
|
||
|
|
(d) CH 3 — C — Ph
(a) CH 3 — C — Ph (b) CH 3 — CH — Ph (c) Ph — C — Ph
|
|
Ph
Ph
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157
6.
In which of the following reactions product formed is same ?
O
MgX
MeMgX
(i)
P
(ii)
P
O
O
||
(iii)
MgBr
(a) (i) and (ii)
7.
¾¾® P
(b) (ii) and (iii)
(c) (i) and (iii)
(d) (i), (ii) and (iii)
Which of the following reaction sequences would be the best for synthesis of 2-pentanone ?
O
||
CH 3 MgI
H 3O Å
(a) CH 3 — CH 2 — CH 2 — C — H ¾ ¾¾
¾® ¾ ¾¾
¾®
Et 2O
(b)
CH 2 — CH 2
CH 3 MgI
H 3O Å
¾ ¾¾
¾® ¾ ¾¾
¾®
|
|
Et 2O
CH 3 — CH — O
H OÅ
CH MgI
3
3
(c) CH 3 — CH 2 — CH 2 — C ºº N ¾ ¾¾
¾® ¾ ¾¾
¾®
Et 2O
O
||
CH 3 MgI
H 3O Å
(d) CH 3 — CH 2 — C — H ¾ ¾¾
¾® ¾ ¾¾
¾®
Et 2O
(Propanal)
OH
CO2CH3
8.
CO2CH3
9.
x CH3MgI
C(CH3)2
; Dimethyl phthalate
H+
C(CH3)2
OH
Number of moles ( x) of Grignard reagent consumed in the above reaction is :
(a) 2
(b) 3
(c) 4
(d) 5
OH
|
Ph — C — CH 3
|
CH 2 - CH 3
Which of the following combinations can not be used to prepare alcohol given above ?
O
||
(a) PhMgBr + 2-butanone ¾ ¾¾
(b) EtMgBr + Ph - C -CH 3 ¾ ¾¾
¾®
¾®
NH 4Cl
NH 4Cl
O
O
||
||
(d) EtMgBr + Ph - C -CH 2 - CH 3 ¾ ¾¾
(c) CH 3 MgBr + Ph - C -Et ¾ ¾¾
¾®
¾®
NH 4Cl
NH 4Cl
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158
10.
O
(1) CH 3 MgBr
||
(excess)
¾® (A), Product (A) is :
Et — O — C — O — Et ¾ ¾¾¾¾
Å
(2) H 3O
O
||
(b) CH 3 — C — CH 3
O
||
(a) CH 3 — C — O — Et
OH
|
(c) CH 3 - C - CH 3
|
CH 3
(d) CH 3 — CH 2 — CH 3
O
O
11.
O
H+
¾¾
¾® (A). Product (A) is :
PhMgBr +
excess
O
||
(a) Ph — C — Ph
OH
|
(b) Ph— C — Ph
|
Ph
OH
|
(c) Ph – C
|
Ph
O
||
(d) Ph – C – O
O
¾ ¾¾¾
¾® ( P ) . Product (P) is :
CH 3 MgBr
C – NOCH3 +
5% HCl
> 90%
Methyl magnesium
|
H 2O
bromide 75 equivalent
CH3
12.
N-Methoxy-N-methyl
benzamide 1-equivalent
OH
|
(a) Ph— C — Ph
|
Ph
13.
OH
|
(b) Ph— C — CH 3
|
CH 3
O
||
(c) Ph — C— CH 3
O
||
(d) Ph — C — Ph
Point out the incorrect synthesis :
OH
MgBr
(a)
O
||
(1) CH 3 -C -CH 3
¾ ¾¾¾¾¾
¾®
+
( 2) H
OH
|
CH – Ph
Br
(1) Mg,ether
(b)
¾ ¾¾¾¾®
N
|
H
(2) Ph -CHO
(3) H 3O Å
N
H
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(c) PhMgBr +
CH2 – CH2
(1)
O
¾¾¾¾¾®
Ph —
(2) H+
CH 2 — CH 2 — OH
(1) HCHO
(d) PhMgBr + ¾ ¾¾
¾
® Ph — CH 2 — OH
+
(2) H
14.
O
14
||
NaH CO 3
(i) PhMgBr
® ( A) ¾ ¾¾¾¾® (B)
CH 3 — C — O — H ¾ ¾¾¾
( ii) H 3O Å
(gas)
O
14
||
(i) PhMgBr
NaH CO 3
® (C ) ¾ ¾¾¾¾® (D)
CH 3 — S — O — H ¾ ¾¾¾
( ii) H 3O Å
||
gas
O
Product (B) and (D) in the above reaction are :
O
O
O
O
||
||
||
||
(a) Ph — C— O — H, Ph — S — O — H
(b) Ph - C - O - H, Ph - S - O - H
14
||
O
O
O
O
O
||
||
||
||
(d) Ph — C — OH, Ph — S — O — H
(c) Ph — C— O — H, Ph — C — O — H
14
14
(1) MeMgBr,
THFOºC
OH
15.
OEt
OLi
(A); Product (A) in this sequence is :
(2)
O
(a)
(3) H+,
O
(b)
OH
OH (c)
(d)
OH
OH
O
CH MgBr
diethyl ether
NH Cl
H 2O
4
3
¾ ¾¾¾
¾® ¾ ¾¾
¾® Products.
16.
CH3
Comment on optical activity of the products. They are :
(a) racemic mixture
(c) meso forms
(b) diastereomers
(d) optically inactive due to absence of chiral centre
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160
17.
In which of the following reaction an acid-base reaction takes place ?
CH2MgCl
H
H
O
(a)
HBr in water
(b)
O
MgCl
Li
D
O
(c)
(d) All of these
H SO
(1) 2PhMgBr
2
4
¾ ¾¾¾¾
¾® A ¾ ¾¾
¾
® (B), Product (B) in this reaction is :
18.
(2) H 2O
O
O
D
18
(a)
(b)
O
19.
Ph
O
Ph (d)
Ph
O
18
O
18
Ph
Ph
All of the following compounds react with ethylmagnesium bromide. Alcohols are formed
from three of the compounds. Which one does not give an alcohol ?
O
O
(a)
(b)
CH
COCH3
O
||
(d) Ph - O - C - O - H
O
||
CH2OCCH3
(c)
20.
(c)
Ph
A student was carrying out a Grignard reaction between PhMgBr and ethyl benzoate. She ran
out of anhydrous ether just after the Grignard reagent was made. Which of the following
solvents can still be used to dissolve the ethyl benzoate for its reaction with already formed
PhMgBr ?
(a) acetone
(b) ethyl acetate
OH
MeO2C
21.
(c) absolute alcohol
H
N
Ph Ph
t–Bu
(1) x PhMgBr
¾ ¾¾¾¾
¾®
HO
(2) H 3O Å
(d) benzene
OH
H
N tBu
HO
HO
Number of equivalents of Grignard reagent ( x) used in reaction (1) is :
(a) 3 equivalent
(b) 4 equivalent
(c) 5 equivalent
(d) 6 equivalent
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OH
|
CH – Ph
Br
(1) Mg; ether
22.
¾ ¾¾¾¾®
(2) Ph -CHO
N
N
(3) H 3O Å
|
|
H
H
The given product can not be obtained in the above reaction. Identify the correct product
obtained.
OH
O
|
CH – Ph
CH – Ph
(a)
(b)
(c)
(d)
N
N
N
|
CH – Ph
|
OH
Which of the following gives two isomers of 3° alcohol, when treated with
phenyl magnesium bromide ?
CH – Ph
|
OH
N
|
H
23.
(a)
(b)
O
O
D
(c)
D
(d)
O
O
Me
O
H
MeMgBr
24.
¾ ¾¾¾® Product of the reaction is :
H Ph
Me
Me
Me
H
(a)
Me
H
(b)
HO
Ph
H
(c) Both (a) and (b) (d) None of these
H
Ph
OH
RMgBr
25.
¾ ¾¾
¾® Product; The product of the reaction is :
S
O
O
(a) HSO 2 — CH 2 — CH 2 — CH 2 — CH 2 — R
(b)H — SO 2 (CH 2 ) 3 — R
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(c)
SO2
26.
(d) H — SO 2 (CH) 3 — R
MgBr
When carboxylic acid reacts with organolithium reagents to give ketones, side reaction
sometimes occur. For example,
CH 3
O
|
||
NH 4Cl
( x ) CH 3 Li
¾® ¾ ¾¾
¾®
HOCH 2CH 2 CH CH 2 CH 2 C OH ¾ ¾¾¾
H2
tetrahydro furan
CH 3
O
|
||
HOCH 2CH 2 CH CH 2 CH 2 - C - CH 3 + compound (B)
Compound A 63%
37%
Value of (x) in above reaction is :
(a) 2
27.
(b) 3
(c) 4
(d) 5
Which of the following alcohol can not be prepared by the reaction of acid chloride with
excess of Grignard reagent followed by acidification ?
OH
OH
(a) Ph
Ph
(b) Ph
(c) Et
CH3
CH3
CH3
OH
OH
Et
CH3
Et
(d) CH3
Ph
O
H
(i) MeMgI
¾® ( B ) ;
¾ ¾¾¾
¾® (A) ¾ ¾
D
+
28.
(ii) NH 4Cl
(major)
Product (B) of the above reaction is :
CH2
||
29.
(a)
(b)
(c)
(d)
The reaction of elemental sulphur with Grignard reagent followed by
acidification leads to the formation of
(a) mercaptan
(c) thioether
(b) sulphoxide
(d) sulphonic acid
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THF
+ MgBrCH 2 CH 2 CH 2 CH 2 MgBr ¾(i)
¾¾
¾® product; Product of the reaction is :
30.
O
(ii) H 3O +
O
O
||
(a) HO — (CH 2 )3 — C — CH 2 — CH 2 — CH 3(b)
HO
(c) HO
O
(d)
CH — CH 2 — CH 3
|
OH
C — Cl
31.
HO
OH
|
C — CH3
|
CH3
(i) x CH3MgBr
(ii) H +
C — Cl
(CH2)3 — OH
CH2 — CH2 — CH3
C
OH
Me
Number of moles of CH 3 MgBr consumed in above reaction is :
Me
O
(a) 2
32.
(b) 4
(c) 6
(d) 8
End product of the given reaction is :
Cl
Mg
1.CH O
Et 2O
2. H 3O Å
¾ ¾¾® ( A) ¾ ¾¾2¾® (B)
OH
(a)
OH
(b)
OH
(c)
33.
(d)
Which of the following compound is not a suitable solvent for Grignard reaction ?
O
(a)
(b)
O
O
(THF)
(1, 4-dioxane)
(c) CH 3 — O — CH 2 — CH 2 — O — CH 3 (d)
Br
34.
(2 mole)
(a)
35.
Mg
¾ ¾¾® Predict major product of the reaction :
Et 2O
(b)
(c)
(d)
Which of the following reaction sequences would be the best for synthesis of t-butyl alcohol ?
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O
Et O
H 3O
2
(a) CH 3 CH 2 MgBr + CH2 – CH2 ¾ ¾¾
® ¾ ¾¾
¾®
CO
Et 2O
Å
H OÅ
2
3
(b) CH 3 CH 2 CH 2 MgBr ¾ ¾¾
® ¾ ¾¾
¾®
O
||
Et 2O
H 3O Å
(c) CH 3 MgBr + CH 3 — C — CH 3 ¾ ¾¾
® ¾ ¾¾
¾®
O
||
Et 2O
H 3O Å
(d) CH 3 CH 2 MgBr + CH 3 — C — H ¾ ¾¾
® ¾ ¾¾
¾®
36.
What is the major product of the following reaction ?
H OÅ
CH MgI
3
3
CH 3 — C ºº N ¾ ¾¾
¾® ¾ ¾¾
¾®
Et O
2
H
N
(b) CH3 – C – CH3
(a) CH 3 — CH 2 — NH — CH 3
O
||
(c) CH 3 — C — CH 3
H
C
37.
CH3
O
||
(d) CH 3 — CH 2 — C — OH
PhMgBr
(1)
¾ ¾¾¾¾® Products; Product obtained in this reaction are :
(2) H+
O
(a) diastereomers
38.
(b) racemic
(c) pure enantiomer (d) meso
CH 3 CO 2 Et + (CH 2 ) 5 (MgBr) 2 ¾ ¾¾¾
® C 7 H 14 O ; compound (A) will be :
+
(2) H
(A)
OH
OH
(a)
(b)
OH
O
||
(c) CH 3 — C — (CH 2 ) 4 — CH 3
(d)
O
C – Ph
39.
(1) PhMgBr CuCl
¾ ¾¾¾¾¾¾® ( A) ; A will be :
(2) H+
C19 H 20O
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OH
|
h
C –P
|
Ph
(a)
O
O
C – Ph
C – Ph
Ph
(b)
(c)
O
||
C – Ph
(d)
Ph
Ph
MeO
OMe
40.
n - Bu 2Cu Li
¾ ¾¾¾¾¾¾¾
¾® Product of the reaction will be :
(n - Bu = n - butyl group)
Br
MeO
OMe
MeO
(a)
OMe
(b)
n-Bu
n-Bu
OMe
OH
Bu
(c)
OH
(d)
Br
O
||
Cl -C -O - Me
Li
41.
Br
¾ ¾¾¾¾® (?) ; Product of this reaction is :
CO2Me
Cl
(a)
42.
(b)
(c)
Ethyl acetoacetate when reacts with one mole methyl magnesium iodide then product of
reaction will be :
O
O
||
||
(a) CH 3 — C — CH 2 — C — CH 3
OQMgBr
O
(b) CH3 — C — CH2 — C — CH3
CH3
O
||
(d) CH -2 — C — CH 2 — CO 2 Et
O
Q
(c) CH3 — C — CH — CO2Et
43.
(d)
MgBr
O
||
CH 3 MgBr + Et ¾ O ¾ C ¾ O ¾ Et ¾¾® ( A); Product A is :
( excess)
(2) H Å
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OH
O
OH
(a)
44.
(b)
OH
(c)
(d)
C H MgI
H 2O H
2 5
For the sequence of reactions, A ¾ ¾¾¾
® B ¾ ¾¾¾
® tert-Pentyl alcohol. The
ether
+
compound A in the sequence is :
(a) 2-Butanone
(b) Acetaldehyde
45.
(c) Acetone
(d) Propanal
O
||
(1) excess CH 3 - Li
¾
®
A
® (A)
PhMgBr + CH 3 - CN ¾ ¾¾
(
)
Ph
C - O - H ¾ ¾¾¾¾¾¾
Å
H 3O
(2) H 3O
Same product (A) will form in both reactions. A is :
OH
O
|
||
(c) Ph — C — CH 3 (d) Ph — CH 2 — CO 2 H
(a) Ph — C — CH 3 (b) Ph — CHO
|
CH 3
46.
47.
Which of the following Grignard reagent can be prepared ?
(a) Br — Mg — CH 2 — CH 2 — CH 2 — O — H (b) Br — Mg — CH 2 — CH 2 — SH
(c) BrMg — CH 2 — CH 2 — NH 2
(d) BrMg — CH 2 — CH 2 — N — CH 3
|
In the reaction sequence :
CH 3
O
(i) CH MgBr CuCl
3
¾ ¾¾¾¾¾¾
® (X), Product (X) will be :
+
(ii) H 2O H
CH3
O
OH
O
H
(a)
(b)
(c)
CH3
48. (C 2 H 5 O) 2 CO
CH 3 MgBr(excess)
¾ ¾¾¾¾¾
¾®
H 3O+
CH3
(d)
OH
CH3
A. A (alcohol) can also be obtained by :
(a) CH 3 CH 2 CHO ¾ ¾¾¾¾¾
¾®
O
||
CH 3 MgBr(2 mol)
(b) CH 3 C OC 2 H 5 ¾ ¾¾¾¾¾
¾®
+
O
||
CH 3 MgBr (1mol)
(c) CH 3 C CH 3 ¾ ¾¾¾¾¾
¾®
(d) as in (b) and (c)
CH 3 MgBr(2mol)
H 3O+
H 3O +
49.
OH
CH3
H 3O
The principal product of the reaction between methyl butanoate and 2 moles of CH 3 MgBr
after hydrolysis is :
(a) C 3 H 7 COCH 3
(c) C 3 H 7 CHOHCH 3
(b) C 3 H 7 C(OH)(CH 3 ) 2
(d) C 3 H 7 COCH(CH 3 ) 2
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50.
Which of the following compounds will form hydrocarbon on reaction with Grignard reagent ?
(a) CH 3 CH 2 OH
51.
(b) CH 3 CHO
(c) CH 3 COCH 3
(d) CH 3 CO 2 CH 3
What is the product ( B ) of the following reaction sequence ?
Br
Mg
¾ ¾¾® A
Et 2O
O
A +
CH3
(1) Et O
(2) H 3O
2
¾ ¾¾¾
®B
Å
O
OH
(a)
CH3
CH3
OH
(b)
CH3
OH
OH
(c)
(d)
CH3
OH
52.
Which, if any, of the following pairs of reagents could be used to prepare 2-phenyl-2-butanol?
O
O
||
||
(b) CH 3 CH 2 MgBr + C 6 H 5 CH 2 C H
(a) CH 3 CH 2 MgBr + Ph — C — CH 3
O
O
||
||
(d) C 6 H 5 MgCl + CH 3 C CH 2 CH 2 CH 3
(c) CH 3 MgI + C 6 H 5 CH 2 C CH 3
53.
What is the product of the following reaction?
1. diethyl ether
+ 2CH 3 MgBr ¾ ¾¾¾¾¾® Product
O
O
(a) HO – CHC H 2 CH 2 CH 2 CH – OH
|
|
CH 3
CH 3
CH 3
|
(c) HOCH 2 CH 2 CH 2 CH 2 C — OH
|
CH 3
Ph
54.
Br
Mg
ether
A
1. HCHO
2. H+
2. H 3O +
(b) CH 3OCH 2 CH 2 CH 2 CH 2 CHC H 3
|
OH
(d) HOCH 2 CH 2 CH 2 CH 2 CHO CH 3
|
CH 3
B
; Product (B) is :
Ph
(a)
CH2 — OH
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(b) Ph — C ºº C — CH 2 — CH 2 — CH 2 — OH
(c) Ph — C ºº C — CH 2 — CH 2 — OH
(d) Ph — CH 2 — C ºº C — CH 2 — CH 2 — OH
55.
What sequence of steps represents the best synthesis of 4-heptanol (CH 3 CH 2 CH 2 ) 2 CHOH ?
(a) CH 3 CH 2 CH 2 MgBr (2moles) + formaldehyde (H 2 C = O) in diethyl ether followed by
H 3O +
(b) CH 3 CH 2 CH 2 MgBr + butanol (CH 3 CH 2 CH 2 CH = O) in diethyl ether followed by H 3 O +
(c) CH 3 CH 2 CH 2 CH 2 MgBr + acetone [(CH 3 ) 2 C = O] in diethyl ether followed by H 3 O +
(d) (CH 3 CH 2 CH 2 ) 2 CHMgBr + formaldehyde (H 2 C = O) in diethyl ether followed by H 3 O +
O
Et
(1) MeMgBr
(2) NH 4Cl
¾ ¾¾¾¾® Comment on stereochemistry of products :
56.
H
Me
(a) diastereomers
(c) single stereoisomer
(b) racemic
(d) meso
CH2 — OH
|
57. CH —OH + CH 3 MgBr —® xCH 4
|
(Excess)
CH2 — SH
What is the value of x in the above reaction ?
(a) 1
58.
(b) 2
(c) 3
0.40 g of an organic compound (A), (M.F.- C 5 H 8 O) reacts with x mole of CH 3 MgBr to
liberate 224 mL of a gas at STP. With excess of H 2 , (A) gives pentan-1-ol. The correct
structure of (A) is :
(a)
(b)
(c)
(d)
CH 3 — C ºº C — CH 2 — CH 2 —OH
CH 3 — CH 2 — C ºº C — CH 2 — OH
H — C ºº C — CH 2 — CH 2 — CH 2 — OH
H — C ºº C — CH 2 — CH — CH 3
|
OH
59.
(d) 4
Br2
Mg
hn
(low conc.)
Dry ether
CH 3 — CH == CH 2 ¾ ¾¾¾¾® ¾ ¾¾¾
¾®
O
||
CH 3 -C -CH 3
¾ ¾¾¾¾
¾®
NH 4Cl
H+
¾¾
¾® ( X )
D
(major)
End product (X) of the above reaction is :
CH 2
||
(a) CH 2 == CH — CH 2 —C — CH 3
(b) H 2 C == CH —CH == C — CH 3
|
CH 3
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OH
|
(c) H 2 C == CH — CH 2 —C — CH 3
|
CH 3
(d) H 2 C == CH — CH 2 — CH — CH 2 — OH
|
CH 3
60.
Mg
3I
CH2 — CH — CH2 — Br ¾ ¾¾¾¾® ( A) ¾ CH
¾¾
® ( B ) ; Product (B) is :
dry ethane
O
(a) CH2 — CH — CH2 — CH3
O
(b) CH 3 — O — CH 2 — CH 2 — CH 3
(c) H 2 C == CH — CH 2 — O — CH 3
(d) H2C — CH — CH3
O
61.
Compound A was treated with a large excess of CH 3 MgBr . The resulting product was
exposed to POCl 3 pyridine to give compound B , as one of many products :
B
Which of the following compounds can be A ?
O
O
(a)
H
H
(b)
O
(c)
62.
(d)
Identify product Z in the following reaction sequence :
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170
1. C 6 H 5MgBr,
diethylether
NaCN
H 2 C == CHCH 2 Br ¾ ¾¾® Y ¾ ¾¾¾ ¾¾® Z
2. H 3O +
O
O
||
||
(a) H 2 C == CHCH 2 C C 6 H 5
(b) H 2 C == CHCH 2 NHC C 6 H 5
NH 2
OH
|
|
(c) H 2 C == CHCH 2CH C 6 H 5
O
63.
(d) H 2 C == CHCH 2 CH C 6 H 5
O
CH3MgBr
Cl
(Consider all steps and intermediate) correct statement is :
(a) Nucleophilic addition
(c) Product obtained is chiral
64.
(b) Nucleophilic substitution reaction
(d) All
Which combination(s) of alkyl bromide and epoxide can be used to prepare the following
product by addition of the Grignard reagent derived from the alkyl bromide to the epoxide ?
OH
Br
(a)
O
(b)
,
,
O
O
(c)
65.
O
Br
(d)
What will be the final major product ?
S
CH - I
RMgX
3
¾ ¾¾
¾® (I) ¾ ¾¾
¾® (II)
O
18
S
(a)
(b)
SH
R
(c)
SH
18
S
O
R
O
(d)
18
OCH3
R
18
SCH3
R
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66.
Give the expected product of the following reaction.
O
1. MeMgBr (excess)
O
2. H2O
Cl
O
(a)
(c)
H3CO
H3C
O
OH
(b)
CH3
CH3
(d)
O
HO
OH
CH3
HO
H3C
CH3
OH
HO
CH3
ANSWERS — LEVEL 1
1.
(b)
2.
(d)
3.
(b)
4.
(d)
5.
(c)
6.
(d)
7.
(c)
8.
(c)
9.
(d)
10.
(c)
11.
(b)
12.
(b)
13.
(b)
14.
(c)
15.
(b)
16.
(b)
17.
(d)
18.
(d)
19.
(d)
20.
(d)
21.
(c)
22.
(b)
23.
(b)
24.
(c)
25.
(c)
26.
(b)
27.
(d)
28.
(d)
29.
(a)
30.
(b)
31.
(b)
32.
(b)
33.
(d)
34.
(b)
35.
(c)
36.
(c)
37.
(b)
38.
(b)
39.
(b)
40.
(a)
41.
(b)
42.
(c)
43.
(b)
44.
(c)
45.
(c)
46.
(d)
47.
(b)
48.
(d)
49.
(b)
50.
(a)
51.
(a)
52.
(a)
53.
(c)
54.
(b)
55.
(b)
56.
(a)
57.
(c)
58.
(c)
59.
(b)
60.
(c)
61.
(d)
62.
(a)
63.
(d)
64.
(b)
65.
(c)
66.
(d)
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172
Level - 2
1. Comprehension
Grignard reagent is usually prepared by
Et O
R - X + Mg ¾ ¾2¾® RMgX
Grignard reagent
Et 2O
Ar - X + Mg ¾ ¾¾® ArMgX
Grignard reagent
Grignard reagent acts as a strong base. Grignard reagent carry out nucleophilic attack in
absence of acidic hydrogen. Grignard reagent form complex with its ether solvent.
Complex formation with molecule of ether is an important factor in the formation and
stability of Grignard reagent.
A.
What is the correct order of reactivity of halides with magnesium ?
(a) R - Cl > R - Br > R - I
(c) R - I > R - Br > R - Cl
B.
(b) R - Br > R - Cl > R - I
(d) R - I = R - Br = R - Cl
Which of the following will undergo acid-base reaction with Grignard reagent ?
(a) HC º CH
(c) R - CO 2 H
C.
(b) R - OH
(d) All of these
Which of the following reactants give primary alcohol as a major product when reacts with
RMgX followed by acidification ?
(i) CH — CH
2
2
O
||
(ii) H - C - H
(iii) CH2 — CH — CH3
O
O
O
||
(iv) C H 3 - C -H
D.
(v)
O
(vi)
(a) i, ii, v
(b) i, ii, v, vi
(c) ii, iv, vi
O
||
(1) xRMgX
Cl - C -O - Et ¾ ¾¾¾¾® 3° alcohol. Value of x is :
O
(d) v, iv, iii, vi
(2) NH 4Cl
(a) 2
E.
(b) 3
(c) 4
(d) 5
O
OH
||
|
(1) x PhMgBr
¾® HO - CH 2 - CH 2 - C - Ph, Value of x is :
H - O - CH 2 - CH 2 - C - O - Et ¾ ¾¾¾¾
(2) H +
|
Ph
(a) 2
(b) 3
(c) 4
(d) 5
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F.
Which of the following Grignard reagents is not possible ?
(a) HS - CH 2 - CH 2 - CH 2 MgBr
(c) NH 2 - CH 2 - CH 2 - CH 2 MgBr
G.
(b) HO - CH 2 - CH 2 - CH 2 MgBr
(d) All of these
How many different Grignard reagents when react with EtOH, give n-butane as product
(excluding stereoisomerism).
(a) 1
(b) 2
2. Match the column I and II. (Matrix)
(c) 3
(d) 4
Column (I)
Column (II)
Reactant
O
||
(a)
®
PhMgBr + Cl - C - O - Et ¾ ¾¾
Å
(p)
Ph – CH 2 – OH
(q)
Ph - CH - Ph
|
OH
(r)
OH
|
Ph — C — Ph
|
Ph
(s)
OH
|
Ph — C — Ph
|
CH3
H
(excess)
O
||
(b)
PhMgBr + H - C - O - Et ¾ ¾
¾
®
Å
H
(excess)
O
||
(c)
PhMgBr + H - C - H ¾ ¾
¾
®
Å
(excess)
Product
H
O
||
(d)
PhMgBr + CH 3 - C - O - Et ¾ ¾
¾
®
Å
H
(excess)
3. Match the column I and II. (Matrix)
Column (I)
Column (II)
Reaction
¾® 1ºalcohol
(a) PhMgBr + (A) ¾ ¾
HÅ
(p)
¾® 2ºalcohol
(b) PhMgBr + (B) ¾ ¾
HÅ
(q)
¾
¾
® 3ºalcohol
(c) PhMgBr + (C) ¾ H
Å
(r)
¾
¾
®
(d) PhMgBr + (D) ¾ H
Å
(s)
Reactant
O
O
||
||
CH 3 - C - CH 2 - C - CH 3
O
||
CH 3 - C - CH 3
O
||
CH 3 - C - H
O
||
H - C -H
Match the missing reactant A, B, C, D
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4. Match the column I and II. (Matrix)
(a)
Column (I)
Column (II)
Reaction
Moles of
PhMgBr used
O
||
¾
® 3ºalcohol
PhMgBr + Et - O - C - O - Et ¾ ¾
Å
(p)
1
O
||
¾
® 3° alcohol
PhMgBr + HO - CH 2 - C - CH 3 ¾ ¾
Å
(q)
2
O
||
¾
® 3ºalcohol
PhMgBr + CH 3 - C - CH 3 ¾ ¾
Å
(r)
3
(s)
4
H
(b)
H
(c)
H
(d)
HO
PhMgBr +
O
||
C – Cl
¾¾
¾
® 3ºalcohol
Å
H
HO
5.
When 20 g of a compound (A) (M.F. = C 4 H 10O 4 ) reacts with excess of CH 3 MgBr, 14.6 L of
CH 4 is obtained at STP. What is structural formula of (A) ?
CH2— OH
|
(a) (CH — OH) 2
|
CH2— OH
HO
CH 2 OH
|
(b) HO — CH 2 — C — CH 2 OH
|
OH
OH
(c)
(d) Both (a) & (b)
HO
OH
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Subjective Problems
1.
MgBr
H
O
OH
r
excess
H
r
H
D
(X)
How many geometrical isomer of (X) is possible ?
2.
How many isomer of C 4 H 8 O when reacts with CH 3 MgBr followed by acidification to give 2º
alcohol (only consider carbonyl isomers)?
(including stereoisomer)
3.
Total number of RMgX are consumed in the following reaction
Cl
O
CººN
x RMgX
O
O
O
4.
How many isomers of C 4 H 10 O reacts with CH 3 MgBr to evolve CH 4 gas ? ( Excluding
stereoisomer)
5.
How many carbonyl isomers of C 5 H 10 O which reacts with PhMgBr to give racemic mixture ?
6.
How many moles of Grignard reagent will consume when it reacts with following
compound?
O
CH==O
C—Cl
HO
C—O—Et
H—S
C
O
N
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ANSWERS — LEVEL 2
1.
A – c; B – d; C – a; D – b; E – b; F – d; G – b
2.
a – r; b – q; c – p; d – s
3.
a – s; b – r; c – q; d – p
4.
a – r; b – q; c – p; d – s
5.
(d)
Subjective Problems
1. 4
2. 2
3. 7
4. 4
5. 5
6. 8
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4A
HYDROCARBONS (ALKANES)
Level - 1
1.
On halogenation, an alkane gives only one monohalogenated product. The alkane may
be :
(a) 2-methyl butane
(b) 2, 2-dimethyl propane
(c) cyclopentane
(d) both (b) and (c)
2.
Which of the following compounds can be best prepared by Wurtz-reaction ?
(a) Iso-butane
(b) n-butane
(c) n-pentane
(d) Iso-pentane
3.
A hydrocarbon A (V.D. = 36) forms only one monochloro substitution product. A will be :
(a) iso-pentane
(b) neo-pentane
(c) cyclohexane
(d) methyl-cyclohexane
4.
Ethyl iodide and n-propyl iodide are allowed to undergo Wurtz reaction. The alkane which
will not be obtained in this reaction is :
(a) butane
(b) propane
(c) pentane
(d) hexane
5.
Cl 2
¾®
CH 3 — CH — CH 2 — CH 3 ¾ ¾
hn
|
CH3
Number of chiral centers generated during monochlorination in the above reaction :
(a) 1
(b) 2
(c) 3
(d) 4
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6.
7.
CH 3Cl —® CH 4
Above conversion can be achieved by :
(a) Zn / H +
(b) LiAlH 4
(c) Mg / (ether) then H 2O
(d) all of these
Cl 2 / hn
n-Butane ¾ ¾ ¾
¾®
Give the total number of monochloro products(including stereoisomers), which are possible
in the above reaction.
(a) 2
(b) 3
(c) 4
(d) 5
8.
hn
CH 4 + Cl 2 ¾ ¾
® CH 3Cl + HCl
To obtain high yields of CH 3 Cl, the ratio of CH 4 to Cl 2 must be :
(a) high
(b) low
(c) equal
(d) can't be predicted
9.
Double bond equivalent of cubane is :
Cubane
(a) 4
10.
(c) 6
(d) 7
How many bond cleavages are required to convert cubane into non-cyclic skeleton ?
(a) 2
11.
(b) 5
Cubane
(b) 3
Non-cyclic skeleton
(c) 4
(d) 5
Draw an energy profile diagram for a three step reaction in which first step is slowest and last
step is fastest. (Assume that reaction is exothermic)
PE
PE
(a)
(b)
progress of reaction
progress of reaction
PE
(c)
(d) None of these
progress of reaction
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12.
Cl 2
CH 3 ¾ CH ¾ CH 2 ¾ CH 3 ¾¾® (x) = Number of monochloro product including
hn
|
CH 3
stereoisomers.
(a) 4
(b) 5
ND2—ND2
(d) 7
(P)
H2O2
13.
(c) 6
Product (P) is :
(a)
14.
(A)
D
(b)
D
D
(c)
D
H2(1mole)/Pt
Double bond equivalent (degree of Unsaturation) of (A) is :
(a) 1
(b) 2
(c) 3
15.
(d) both (b) & (c)
(d) 4
Arrange the following alkanes in decreasing order of their heats of combustion.
CH3
|
(i) CH 3 — C — CH 3
|
CH3
(ii) CH 3 — CH — CH 2 — CH 3
|
CH3
(Iso - pentane) (ii)
(Neo - pentane) (i)
(iii)CH 3 — CH 2 — CH 2 — CH 2 — CH 3
( n- pentane )
(a) (i) > (ii) > (iii)
(c) (iii) > (ii) > (i)
H
16.
CH3
+ H2
CH2
(b) (iii) > (i) > (ii)
(d) (i) > (iii) > (ii)
Pd
Product of the above reaction will be :
(a) Racemic mixture
(c) Meso
CH3
Br
H
17.
(b) Diastereomers
(d) Constitutional isomers
CH2
+ Br2
300°C
CH2—CH3
Which of the following compound will not be obtained as a product in the above reaction ?
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CH3
CH3
Br
H
(a)
H
Br
H
Br
(b)
Br
H
CH2
CH3
CH2
CH3
CH3
H
(c)
Br
Br
H
H
Br
(d)
CH2
Br
H
CH3
CH3
CH2
CH3
18.
Following are the structures of four isomer of hexane. Among the names given below, which
correctly identifies the fifth isomer ?
CH 3CH 2CH 2CH 2CH 2CH 3
(CH 3 ) 3 CCH 2CH 3
(CH 3 ) 2 CHCH 2CH 2CH 3
(CH 3 ) 2 CHCH(CH 3 ) 2
(a) 2-Methyl pentane
(b) 2-Ethyl butane
(c) 2,3-Dimethyl butane
(d) 3-Methyl pentane
19.
Which of the following describes the best relationship between the methyl groups in the
chair conformation of the substance shown below ?
CH3
CH3
(a) Trans
(c) Gauche
(b) Anti
(d) Eclipsed
20.
Compare the stabilities of the following two compounds (A) and (B):
A : cis-1-ethyl-3-methyl cyclohexane
B : trans-1-ethyl-3-methyl cyclohexane
(a) A is more stable
(b) B is more stable
(c) A and B are of equal stability
(d) No comparison can be made
21.
Which conformation of ethane has the lowest potential energy ?
(a) Eclipsed
(b) Skew
(c) Staggered
(d) All will have equal potential energy
22.
Ethane is subjected to combustion process. During the combustion the hybrid state of carbon
changes from :
(a) sp 2 to sp 3
(b) sp 3 to sp
(c) sp to sp 3
23.
(d) sp 2 to sp 2
AlCl 3
CH 3 — CH 2 — CH 2 — CH 3 ¾ ¾¾® CH 3 — CH — CH 3
D
|
CH3
Above reaction is an example of :
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(a) isomerization
(c) cracking
24.
25.
26.
(b) polymerization
(d) de-hydrogenation
Which of the following has highest chlorine content ?
(a) Pyrene
(b) DDT
(c) Chloral
Pure methane can be prepared by :
(a) Wurtz reaction
(c) soda-lime de-carboxylation
Calcium carbide + heavy water —® ?
(b) Kolbe electrolysis method
(d) reduction with H 2
The product of the above reaction is :
(a) C 2H 2
(b) CaD 2
27.
CH3 — CH2
(d) Gammaxene
(c) Ca(OD) 2
(d) CD 4
CH3 — CH2
CH3 — CH2
Ethyl cyclopentane
Ethyl cyclohexane
Ethyl cycloheptane
(I)
(II)
(III)
Arrange the compounds I, II and III in decreasing order of their heats of combustion:
(a) II > I > III
(b) I > II > III
(c) III > II > I
(d) III > I > II
28.
An alkane (mol. wt. = 86) on bromination gives only two monobromo derivatives (excluding
stereoisomers). The alkane is :
(a) CH 3 — CH — CH 2 — CH 2 — CH 3
|
CH3
(c) CH 3 — CH — CH — CH 3
|
|
CH 3 CH 3
29.
Order of the bond strength of C — H bonds involving sp , sp 2 and sp 3 hybridized carbon
atoms is :
(a) sp > sp 2 > sp 3
(b) sp 3 > sp 2 > sp
(c) sp 2 > sp 3 > sp
30.
CH3
|
(b) CH 3 — C — CH 2 — CH 3
|
CH3
CH3
|
(d) CH 3 — C — CH 3
|
CH3
(d) sp 2 > sp > sp 3
CH3
CH3
H
CH3
CH3
H
H
H
CH3
H
H
CH3
(I)
(II)
(III)
Among the structures given , select the enantiomers :
(a) I and II
(b) I and III
(c) II and III
(d) I, II and III
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31.
(I)
(III)
(II)
The correct order of reactivity of I, II & III towards addition reactions is :
(a) I > III > II
(b) I > II > III
(c) III > II > I
(d) III > I > II
32.
Br
Cl
Na/Dry ether
(A)
97%
Product (A) of above reaction is :
(a)
(b)
(c)
(d)
33.
Which of the following reactants is suitable for preparation of methane and ethane by using
one step only ?
(a) H 2C == CH 2
(b) CH 3OH
(c) CH 3 — Br
(d) CH 3 — CH 2 — OH
34.
How many carbon atoms does an alkane (not a cycloalkane) need before it is capable to exist
in enantiomeric form ?
(a) 4
(b) 5
(c) 6
(d) 7
35.
Among the following free radical bromination reactions, select those in which 2° halide is the
major product —
CH2 —CH3
(P)
Br2 /hn
Br2/hn
(S)
(a) P, Q, R, S
36.
(A) + Cl2
(Q)
hv
Br2 / hn
(T)
(b) P, R, U
Br2/hn
(R)
Br2/hn
Br2/hn
(U)
(c) P, R, S, T
(d) P, Q, R, S, T
monochloro product
To maximise the yield of monochloro product in the above reaction ?
(a) Cl 2 must be added in excess
(b) Reactant (A) must be added in excess
(c) Reaction must be carried out in dark
(d) Reaction must be carried out with equimolar mixture of Cl 2 and A
37.
Br / hn
CH 3 — CH 2 — CH 2 — CH 3 ¾ ¾2 ¾
¾®
Major product in the above reaction is :
(a) Racemic mixture
(c) Diastereomers
(b) Meso
(d) Constitutional isomers
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38.
Select the chain propagation steps in the free-radical chlorination of methane.
(1) Cl 2 —® 2Cl ·
(2) Cl · + CH 4 —® CH 3Cl + H ·
(3) Cl · + CH 4 —® CH ·3 + HCl
(4) H · + Cl 2 —® HCl + Cl ·
(5) CH ·3 + Cl 2 —® CH 3Cl + Cl ·
(a) 2, 3, 5
(c) 3, 5
CH3
(b) 1, 3, 6
(d) 2, 3, 4
Br2 / hn
39.
Monobromo derivatives
The number of possible monobromo products is (excluding stereoisomers):
(a) 4
(b) 5
(c) 8
(d) 10
CH3 Ha
40.
Hd
Hb
+ Br·
OH
CH2 — Hc
Br · will abstract which of the hydrogen most readily ?
(a) a
(b) b
(c) c
41.
Arrange the following compounds in decreasing order of their heats of combustion :
CH3
CH3
CH3
CH3
CH3
H
H
CH3 CH3
(ii)
(i)
(a) (iii) > (ii) > (i)
(c) (iii) > (i) > (ii)
42.
(d) d
(iii)
(b) (ii) > (i) > (iii)
(d) (i) > (ii) > (iii)
CH 3 — CH 2 — CH 2 — CH 2 — F
a
b
c
d
Arrange the hydrogens a , b, c , d, in decreasing order of their reactivities towards
chlorination:
(a) a > b > c > d
(b) b > c > d > a
(c) b > c > a > d
(d) c > b > a > d
43.
On catalytic reduction ( H 2 Pt ) how many alkenes will give n-butane ?
(a) 1
(b) 2
(c) 3
(d) 4
44.
On catalytic reduction (H 2 Pt) how many alkenes will give 2-methylbutane ?
(a) 1
(b) 2
(c) 3
(d) 4
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Cl2 (excess)/hn
45.
How many dichloro products are formed in the above reaction (including stereoisomers)?
(a) 5
(b) 6
(c) 7
(d) 9
46.
CH3
CH
C
C
D
CH3
H2 / Pt
D
Product of the above reaction will be :
(a) Racemic mixture
(c) Meso
47.
(b) Diastereomers
(d) Constitutional isomers
hn
¾2 /¾
¾
®
Ph — CH 2 — CH — CH 3 ¾ Br
|
D
Product of the above reaction will be :
(a) Diastereomers
(c) Meso
CH2 — Cl
48.
(b) Racemic mixture
(d) Constitutional isomers
(Dry ether)
¾ Na
¾¾
¾¾
¾®
CH3
CH2 — Cl
Products obtained in above Wurtz reaction is :
CH3
(a)
(b)
CH3
CH3
(c)
(d) Both (a) and (b)
CH3
CH3
49.
CH3
Rank the transition states that occur during the following reaction steps in order of
increasing stability (least ® most stable) :
+
1.
H 3C - O H 2 ¾® CH +3 + H 2O
2.
(CH 3 ) 3 C - O H 2 ¾® (CH 3 ) 3 C + + H 2O
3.
(CH 3 ) 2 CH - OH 2 ¾® (CH 3 ) 2 CH + + H 2O
+
+
(a) 1 < 2 < 3
(c) 1 < 3 < 2
(b) 2 < 3 < 1
(d) 2 < 1 < 3
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50.
Which of the following does not represent major product of that reaction ?
Br
Na
(a)
¾ dry
¾ ¾¾
®
ether
Br
Br
(b)
Na
¾ dry
¾ ¾¾
®
ether
Cl
Br
Br
(c) Br
Br
-
¾Ze
¾
¾®
Br
Br
Na
(d) Br
¾ ¾¾
®
Br ¾ dry
ether
ANSWERS — LEVEL 1
1.
(d)
2.
(b)
3.
(b)
4.
(b)
5.
(b)
6.
(d)
7.
(b)
8.
(a)
9.
(b)
10.
(d)
11.
(c)
12.
(c)
13.
(b)
14.
(c)
15.
(c)
16.
(b)
17.
(d)
18.
(d)
19.
(c)
20.
(a)
21.
(c)
22.
(b)
23.
(a)
24.
(a)
25.
(c)
26.
(c)
27.
(c)
28.
(c)
29.
(a)
30.
(c)
31.
(b)
32.
(b)
33.
(c)
34.
(d)
35.
(b)
36.
(b)
37.
(a)
38.
(c)
39.
(b)
40.
(a)
41.
(d)
42.
(c)
43.
(c)
44.
(c)
45.
(c)
46.
(a)
47.
(a)
48.
(d)
49.
(c)
50.
(d)
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Level - 2
1. Comprehension
For the given question (1, 2, 3), consider the following reaction.
+ X2
light
monohalogenation product
A.
Light is involved in which step of the reaction :
(a) Initiation only
(b) Termination only
(c) Propagation only
(d) Propagation and Termination
B.
Which halogen will give the best yield of a single monohalogenation product ?
(a) F2
(b) Cl 2
(c) Br 2
(d) I 2
C.
How many monohalo derivatives are possible (excluding stereoisomers) ?
(a) 3
(b) 4
(c) 5
(d) 6
2. Comprehension
Halogenation is a substitution reaction, where halogen replaces one or more hydrogens of
hydrocarbon.
hn
R — H + X 2 ¾¾
® R — X + HX
alkane
+ Cl·
about 1.5 kcal
difference
in Ea
1°
2° Free radical
3°
PE
PE
less than 1 kcal
difference of Ea
1°
2° Free radical
3°
Progress of the reaction
Chlorination is exothermic and
transition state resembles with products
alkane + Br
Progress of the reaction
Bromination is endothermic and
transition state resembles with products
Chlorine free radical make 1°, 2°, 3° radicals with almost equal ease, whereas bromine free
radicals have a clear preference for the formation of tertiary free radicals. So, bromine is less
reactive, and more selective whereas chlorine is less selective and more reactive.
The relative rate of abstraction of hydrogen by Br · is
3° > 2° > 1°
(1600) (82)
(1)
The relative rate of abstraction of hydrogen by Cl · is :
3° > 2° > 1°
(5) (3.8) (1)
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Consider the above argument and answer A to G :
A.
1-halo-2,3-dimethyl butane will be obtained in better yields, if halogen is :
(a) Br 2
(b) Cl 2
(c) I 2
(d) Can't be predicted
CH3
CH3
X
X2 / hn
B.
Above product will obtained in better yield if X is
(a) Cl 2
(b) I 2
(c) Br 2
C.
(d) Can't be predicted
CH3
|
hn
CH 3 — CH — CH 3 ¾Cl
¾2 /¾
¾
® Product
Major product in the above reaction is :
CH3
|
(b) CH 3— CH— CH 3
|
Cl
(c) CH 3 — CH 2 — CH 2 — Cl
(d) CH 3 — CH— CH 2 — CH 3
|
Cl
Which of the following will give five monochloro products, when allowed to react with Cl 2 in
presence of sun light (excluding stereoisomers) ?
(a) n-pentane
(b) Iso-pentane
(c) 2-methyl-pentane (d) 3-methyl pentane
CH3
|
(a) CH 3 — CH— CH 2 — Cl
D.
E.
CH 3
CH 3
|
|
Br2 hn
CH 3 — C — CH 2 — CH — CH 3 ¾¾¾¾® CH 3 —
|
CH 3
CH 3
CH 3
|
|
C — CH 2 — C — CH 3
|
|
Br
CH 3
2, Bromo- 2, 5, 5 trimethyl pentane (x%)
What is the value of x (% yield of product)?
(a) 18 %
(b) 82 %
(c) 90 %
F.
(d) 60 %
What would be the product ratio x y in the chlorination of propane if all the hydrogen were
abstracted at equal rate ?
2
¾
¾
® CH 3 — CH 2 — CH 2 — Cl + CH 3 — CH — CH 3
CH 3 — CH 2 — CH 3 ¾Cl
hn
|
Cl
(x)
(a)
G.
1
3
(b)
3
1
(c)
(y)
9
1
(d)
1
9
How many dichloro products (including stereoisomers) will be formed when
R-2-chloropentane reacts with Cl 2 in presence of UV radiation ?
(a) 5
(b) 6
(c) 7
(d) 8
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Cl
3.
14
Na
dry ether
¾¾¾® ( A); Product ( A) is :
14
14
14
(a)
14
(b)
(c)
14
(d)
14
14
14
CO2CH3
4.
H2 (1 mole)
Pt
( A); Product ( A) is :
CO2CH3
5.
(a) Meso compound (b) Racemic mixture (c) Diastereomers
O
||
(1)NaOH, CaO, D
Ph ¾ CH 2 ¾ C ¾ OH ¾¾¾¾¾¾®
( A)
Å
(d) Optically active
( 2) H
Product (A) is :
(a) Ph ¾ CO 2H
6.
(b) Ph ¾ CH 2 ¾ OH
(c) Ph ¾ CH 3
(d)
Match the column I with column II and with column III.
Column (I)
Column (II)
Column (III)
Mono-chloro products
Monochloro products
(excluding
stereoisomerism)
(including
stereoisomerism)
Compound
(a)
(p)
1
(w)
1
(b)
CH 3 — CH — CH 2 — CH 3
|
CH 3
(q)
2
(x)
3
(c)
CH 3 CH 3
|
|
CH 3 — C — C — CH 3
|
|
CH 3 CH 3
(r)
3
(y)
5
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(d)
CH 3 — CH 2 — CH 2 — CH 3
(s)
(z)
4
6
7.
A.
2
R-2-chloropentane ¾Cl
¾
¾
® Optically active di-chloro products (P)
hn
2
¾Cl
¾
¾
® Optically active dichloro products (Q)
B.
hn
Cl 2
¾® Optically active di-chloroproducts (R)
C. R-2-chlorobutane ¾ ¾
hn
Sum P + Q + R is :
8. Match the column I and II.
Column (I)
Column (II)
Reaction
Type of Reaction
H
¾ ¾2 ®
(a)
Ni
(p)
Meso compound
(q)
Diastereomers
(r)
Racemic
CH3
2
¾ D¾
®
Pt
(b)
CH3
CH3
CH2
(c)
H
¾ ¾2 ®
Pt
CH3O
H
¾ ¾2 ®
(d)
Pt
H
(s)
Optically inactive due to absence
of chiral center
H
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9. Match the column :
Column (I)
Column (II)
Reaction
Product
CH3
(a)
(1) BD 3 : THF
(p)
CH3
D
T
¾ ¾ ¾ ¾¾®
(2) CH 3CO 2 T
CH3
(b)
(1) BT : THF
(2) CH 3CO 2 D
(q)
CH3
D
H
¾ ¾ ¾3¾¾®
CH3
(c)
(1) BD : THF
(2) CH 3CO 2 H
(r)
CH3
H
D
¾ ¾ ¾3¾¾®
CH3
T
CH3
(d)
(1) BH : THF
¾ ¾ ¾3¾¾®
(2) CH 3CO 2 D
(s)
D
10. How many distinct monochlorinated products, (including stereoisomers) may be obtained
when the alkane shown below is heated in the presence of Cl2 ?
(a) 1
(b) 2
(c) 3
(d) 4
(e) 6
11. How many distinct monochlorinated products, (including stereoisomers) may be obtained
when the alkane shown below is heated in the presence of Cl2 ?
(a) 2
(b) 4
(c) 5
(d) 6
(e) 8
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12. Match the column :
Column (I)
Column (II)
Number of
dimerization product
Wurtz reaction
(a) CH 3 - Cl ¾ ¾Na
¾¾®
dry ether
(p)
5
(b) CH 3 - Cl + CH 3 - CH 2 - Cl ¾ ¾Na
¾¾®
dry ether
(q)
6
(r)
3
(s)
1
(c)
(d)
CH 3 - Cl + CH 3 - CH 2 - Cl
Na
+ CH 3 - CH 2 - CH 2 - Cl ¾ dry
¾ ¾¾
®
ether
H 2C = CH - CH = CH - CH 2 - Cl
Na
+ CH 3 - CH 2 - Cl ¾ dry
¾ ¾¾
®
ether
CH3
13. H
Cl
¾Cl¾2 ® (x). (x) = total number of di-chloro product
CH2—CH2—CH2—CH3
hv
S-2-chloro hexane
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ANSWERS — LEVEL 2
1.
A – a; B – c; C – b
2.
A – b; B – c; C – a; D – c; E – c; F – b; G – c
3.
a, b, c
4.
a
5.
c
6.
a – q – x; b – s – z; c – p – w; d – q – x
7.
P + Q + R = 10
8.
a – q; b – p; c – r; d – s
9.
a – p; b – s; c – q; d – r
10.
a
11.
e
12.
a - s; b - r ; c - p; d - q
13.
9
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4B
HYDROCARBONS (ALKENES)
Level - 1
1.
(R)-3-bromocyclopentene (shown below) reacts with Br 2 CCl 4 to form two products, Y and
Z, Y is not optically active (does not rotate plane-polarized light). What is the structure of Y ?
4
¾ Br
¾2 /CCl
¾¾
®Y + Z
Br
Br
(a)
2.
Br
Br
2HCl
A ¾¾
¾®
(a)
Br
Br
(b)
Cl
Br
Br
(c)
Br
Br
Br
(d)
(e)
Br
Br
Br
. Reactant (A) can be:
Cl
(b)
OH
(c)
(d) All of these
HO
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HCl
3.
; Major product of the reaction is :
CH3
(a)
Cl
(b)
(c)
(d)
Cl
Cl
Cl
O3
4.
Zn
Which of the following products cannot be obtained in ozonolysis of o-xylene?
O O
||
||
CHO
(a) |
(b) CH 3 — C — C — H
CHO
O
||
O
O
||
||
(c) CH 3 — C — C — CH 3
O
||
(d) CH 3 — C — C — CHO
+
O ¾ H¾ ® Major product of the reaction is :
5.
OH
HO
(a)
(b)
(c)
6.
(d)
OH
CH 2 — CO 2K
|
¾ electrolysis
¾¾¾
¾® ( A) (Kolbe electrolysis method)
(major)
CH 2 — CO 2K
Product (A) of the reaction is :
(a) CH 3 — CH 3
(c) CH 3 — CH == CH 2
OH
(b) CH 2 == CH 2
(d) none of these
+
O
Ni
¾ ¾3 ® A ¾ H¾2 ¾
® B ¾ H¾
® (C); Product (C) of the reaction is :
D
7.
Zn
Or LiAlH 4
OH
(a)
O
(b)
(c)
(d)
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Br2
8.
OH
¾ CH
¾¾
¾® W. Product W is :
Cl
2
2
OH
(a)
9.
OH
(d)
Br
O
OH
Br
Br
(c)
Br
(b)
Br
The reaction of propene with H 3O + will proceed with which of the following intermediates ?
Å OH
OH
2
|
|
Å
(b) CH 3 — C H — CH 2
(a) CH 3 — CH 2 — CH 2
Å OH 2
OH
|
|
(c) CH 3 — CH — CH 3
(d)
CH 3 — CH — CH 3
10. Which of the following bromides is the major product of the reaction shown below, assuming
that there are no carbocation rearrangement ?
+
HBr
(1 equivalent)
¾® C 13H 17 Br
Br
Br
(a)
11.
(c) Br
(d)
Br
Which of the following reactions results in the formation of a pair of diastereomers ?
H
CH3
H C
(a) 3
(b)
¾ HBr
¾
¾®
¾ HBr
¾
¾®
CH
(c)
12.
(b)
H3C
H
¾ HBr
¾
¾®
ROOR ,
UV
H
(d)
1. BH 3 , THF
¾ ¾ ¾ ¾ ¾- ¾¾®
2. H 2O 2 , OH , H 2O
What is a likely product of the reaction shown ?
H
H3C
CH3
CH 3OH
¾ Br
¾2 /¾
¾¾®
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H3C
Br
H3C
CH3
OCH3 (b)
(a)
H3C
OCH3
Br
H
CH3
CH3
Br
(c)
CH3
Br
(d)
Br
CH3
OCH3
13.
Which of the following, when undergoing addition of HBr, will form ONLY a pair of
diastereomers ?
H3C
CH3
Cl
H
HO
H
(a)
(b)
(c)
(d)
14.
How many transition states and intermediates will be formed during the course of following
reaction ?
OH
H O, H +
¾ ¾2 ¾¾®
(a) 3 transition states and 3 intermediates (b) 4 transition states and 3 intermediates
(c) 3 transition states and 2 intermediates (d) 5 transition states and 4 intermediates
15.
Product of which of the following reactions, is racemic mixture ?
CH3
¾ H¾2 ®
(a)
Br
(b)
Pt
2
¾¾
¾
®
H3C
CH3
CCl 4
CH3
CH3
H
2
¾¾
®
Pd
(c)
(d) H3C
CH3
Br2
¾ CCl
¾¾®
4
CH3
16.
The product(s) of the following reaction can best be described as :
¾ HBr
¾
¾®
(a) a racemic mixture
(c) a pair of diasteriomers
17.
(b) a single enantiomer
(d) an achiral molecule
Taking into account the stability of various carbocations and, as well as the rules governing
mechanisms of carbocation rearrangements, which reaction is most likely to occur during
the given reaction ?
H – Br
¾®
?
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Br
(a)
Br
¾®
Br
(b)
¾®
(c)
¾®
Br
Br
Br
(d) None
18.
Consider the following reaction in which the intermediate carbocation loses H+ to give the
final product ?
H+
Which of the following energy profiles best represents the overall reaction ?
(a)
(b)
(c)
(d)
19. Methyl vinyl ether, H 2C == CH — OCH 3 , reacts with Br 2 CH 3OH. If methanol is reacting as
water would, and if this reaction follows a typical mechanism of electrophilic addition, what
would be the expected product ?
O
OCH3
OCH3
Br
Br
Br
OCH
Br
(a)
(b)
(c)
(d)
H3CO
OCH3
OCH3
OCH3
20.
2, 4-hexadiyne (C 6 H 6 ) is allowed to react with Li in NH 3 (liq). The product obtained is
treated with 1 equivalent of Cl 2 in CCl 4 . Which of the following constitutional isomers are
possible products ?
Cl
Cl
Cl
(I)
(a) I and II
(c) I and V
21.
Cl
Cl
Cl
Cl
Cl
(II)
(III)
Cl
Cl
(IV)
(V)
(b) II and III
(d) I and III
Which of the following is the best stereochemical representation when reaction between
1-methylcyclohexene and NBS react in aqueous dimethyl sulfoxide ?
OH
OH
Me
Me
(a)
(b)
(c)
(d) None of these
Br
Br
Br
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22.
Which of the following is among the major products of the reaction
(E)-3-methyl-2-pentene with BH 3 in THF followed by the addition of H 2O 2 HO - ?
OH
Me
H
OH
(a)
Et
H
H
Me
Me
(b)
Me
OH
H
Me
(d)
H
H
Et
OH
Me
Et
Et
Compare rate of dehydration of (i), (ii) and (iii) by conc. H 2SO 4 .
OH
OH
(i)
(ii)
(iii)
(a) (i) > (iii) > (ii)
(c) (ii) > (i) > (iii)
24.
(c)
Me
H
Me
23.
H
of
OH
(b) (i) > (ii) > (iii)
(d) (ii) > (iii) > (i)
How many products will be formed in this reaction ?
1. OsO 4
¾ 2.
¾NaHSO
¾¾
¾®
3
(a) 10
(c) 3
(b) 2
(d) 4
H
H
Br
C == C == C
25.
C(CH3)2CH2OH
CH3
2
¾CCl
¾
¾
® (A). Product (A) of the reaction is:
4
Br
Br
(a)
CH3
CH3
CH3
O
(b)
CH3
H
CH3
O
CH3
Br
(c)
CH3
H
CH3
O
CH3
(d)
O Br
CH 3
|
26.
HF
CH 3 — CH + H 2C == CH 2 ¾ 2¾¾
® ( A); (A) is:
- 5°C
|
CH 3
(a)
(b)
(c)
(d) CH 3 — CH — CH 2 — CH == CH 2
|
H
CH 3
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199
27.
Predict the product ( A) of the following reaction
H+
D
(a)
(b)
OH
28.
(a)
29.
A
(c)
H+
D
(d)
(A) Major-product ( A) is:
(Major)
(b)
(c)
(d)
Di-imide (N 2H 4 ) is used to reduce double bond of:
(a) — C == O
(b) — C ºº N
(c) —NO 2
|
(d) — CH == CH —
Na Cr O
7
3
¾H¾¾
® ( B ) ¾ ¾2¾2 ¾
® (C )
¾ HCl
¾
¾®( A) ¾ NaHCO
O
30.
2
C 5 H 8O
End product of the reaction is :
O
OH
O
O
(a)
(b)
HBr
31.
CCl4
(c)
(d)
A
(Major)
Product ( A) is :
Br
Br
Br
(a)
(b)
(c)
(d)
Br
32.
A
)
xcess
H 2(e
Pt
KMn
O4
CO2H
CO2H
+
CO2H
CO2H
Compound (A) is :
(a)
(b)
(c)
(d)
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200
OH
OsO4
33.
X + Y
12 : 1
Product (X) will be :
OH
(a)
OH
(b)
OH
34.
OH
OH
OH
Br2
CH == CH
O
(c)
OH
A
CCl4
2NaNH2
B
(d)
H2
Pd/CaCO3
O
C
Product (C) is :
(a)
Ph
C == C
H
H
Ph
(b)
Ph
H
C == C
MMPP(one-equivalent)
35.
Ph
H
(c)
Ph
C == CH2
Ph
(d) Ph — C ºº C — Ph
X
74%
Ethanol
MMPP ¾® Magnesium mono peroxy phthalate.
Product (X) is :
(a) O
(b)
O
OH
(c) HO
HO
(d)
OH
OMe
MCPBA
36.
P ; Product (P) is :
75%
O
OMe
OMe
O
(a)
(b)
O
O
O
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201
OMe
(c)
(d) None of these
O
O
O
CH3
CH3
O
37.
O
Os
N
O
KOH
N
Mannitol/Water
A ; Product (A) is :
O
Cyclic osmate ester complexed
with pyridine
(a) HO
(b) CH3
CH3
CH3
CH3
OH
OH
(c)
OH
CH3
(d)
O
CH3
CH3
hn
+ CBrCl 3 ¾ ¾
® ( A) (no ring substitution)
38.
Product (A) is :
(a) Ph — CH 2 — Cl
(c) Ph — CH 2 — CCl 3
MCPBA
39.
(b) Ph — CH 2 — Br
(d) Ph — CH 2 — CBrCl 2
(A) ; MCPBA ¾® metachloroperbenzoic acid
Product (A) of the above reaction is :
(a) O
(b)
O
HO
(c)
OH
(d)
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40.
The major product of the following reaction sequence is :
1. B2 H 6
¾ 2.
¾H¾O¾
¾
¾®
, HO
2
OH
(a)
41.
OH
(b)
H
O
HO
(c)
(d)
Which one of the following compounds gives acetone (CH 3 ) 2 C == O as one of the product of
its ozonolysis ?
(a)
42.
?
2
(b)
(c)
(d)
Addition of HCl to 3, 3-dimethyl-1-butene yields two products, one of which has a rearranged
carbon skeleton. Among the following carbocations, select the possible intermediates in that
reaction ?
+
+
(CH 3 ) 3 CCHCH 2Cl
+
(CH 3 ) 3 C C HCH 3
1
2
(a) 1, 2
(e) 2, 4
+
(CH 3 ) 2 C C(CH 3 ) 2
|
Cl
(CH 3 ) 2 C CH(CH 3 ) 2
3
(b) 1, 3
4
(c) 1, 4
(d) 2, 3
43.
Conversion of cyclohexene to cyclohexanol can be conveniently achieved by :
(a) NaOH + H 2O
(b) Br 2 — H 2O
(c) hydroboration, oxidation
(d) hydroboration hydrolysis
44.
Trans-cyclohexane-1,2-diol can be obtained by the reaction of cyclohexene with :
(a) KMnO 4
(b) OsO 4
(c) peroxy formic acid /H 3O +
(d) SeO 2
45.
Bromination of (E)-2-butenedioic acid gives
(a) (2R, 3S)-2, 3-dibromosuccinic acid
(b) (2R, 3R)-2, 3-dibromosuccinic acid
(c) a mixture of (2R, 3R) and (2S, 3S)-2, 3-dibromosuccinic acid
(d) (2S, 3S)-2, 3-dibromosuccinic acid
46.
The major product formed during the reaction of 1-methyl cyclopentene with CH 3CO 3H is
CH3
(a)
CH3
CH3
(b)
OH
(c)
O
CH3
(d)
OH
47.
OH
CH — CO 2H
electrolysis
||
¾ NaOH
¾¾® ( A) ¾¾¾¾¾® ( B ); Product (B) of the reaction is :
CH — CO 2H (two mole)
(a) CH 3 — CH 3
(c) H — C ºº C — H
(b) H 2C == CH 2
(d) CH 2 == CH — CH == CH 2
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203
O–H
Br
2
¾ ¾¾¾
® (lactone)
NaHCO
48.
3
O
(a) HO
(b)
O
O
Cyclic ester
(Bromolactonization)
O
O
Br
Br
(c)
OH
(d)
CO2H
Br
(CF3CO 2 )2 Hg, CH 3CH 2OH
¾ (1)
¾¾¾¾¾¾¾¾¾
® ( P) ; Product (P) is :
-
49.
(2) NaBH 4 , HO
(100%)
Cyclohexene
(a)
(b)
OEt
OH
OCH2CH3
OH
50.
O
O
(c)
(d)
OEt
OH
What is the major product expected from the following reaction ?
KMnO 4
¾ ¾¾¾
®
–
HO cold
(b)
(c)
OH
H
O
Br2 hn
CH 3 - CH == CH 2 ¾ (low
¾¾¾
¾® (A) ; Product (A) of the reaction is :
conc.)
(a) CH 3 — CH — CH 2 — Br
|
Br
(c) CH 3 — C == CH 2
|
Br
O
Et – CH – C
52.
(d)
OH
H
51.
OH
H
H
OH
(a)
OH
OH
OH
O
(b) H 2C == CH — CH 2 — Br
(d) Br — CH 2 — CH 2 — CH 2 — Br
O
Et – CH – C
CH2 – CH
CH2 – CH
C == CH2
; Reagent (A) in the reaction is :
C == O
CH3
(a) O 3 Zn(H 2O)
O
A
CH3
(b) HIO 4
(c) CrO 3
(d) Cold dil. KMnO 4
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204
CH3
1. OsO 4
53.
¾ ¾¾¾
¾® Product of the reaction is:
2. NaHSO
3
CH3
CH3
OH
CH3
CH3
(a)
OH
OH
(b)
H
54.
58.
CH3
H
CH3
Br
Addition of Br 2 to cis-2-butene would give a product which is:
(b) racemic
(d) optically active
Addition of Br 2 to trans-2-butene would give a product which is:
(b) racemic
(c) meso
(d) optically active
Addition of OsO 4 to cyclopentene would give a product which is:
(a) achiral
(b) racemic
(c) meso
(d) optically active
Addition of BH 3 followed by H 2O 2 to trans-2-butene would give a product which is:
(a) achiral
(b) racemic
CH3CHCH = CH2
(c) meso
(d) optically active
CH3CH – CHCH3
|
OH
A
59.
60.
(d)
(d) Br
Br
(a) achiral
57.
OH
CH3
OH
Which compound is a possible product from addition of Br 2 to 1-butene ?
Br
(a)
(b) Br
Br
Br
(a) achiral
(c) meso
56.
(c)
CH3
(c) Br
55.
OH
CH3
; Reagent A may be :
(a) H 2O H +
(b) BH 3 .THF H 2O 2 - OH -
(c) Hg(OCOCH 3 ) 2 . H 2O NaBH 4 .NaOH
(d) All are possible
The major product of the following reaction is :
(C H CO) O peroxide
6 5
2 2
CH 3 — CH == CH 2 + HBr ¾ ¾¾¾¾¾¾¾
®
(a) CH 3 — CH 2 — CH 2 — Br
(b) CH 3CH(Br) — CH 3
(c) BrCH 2 — CH == CH 2
(d)
Br
HO
61.
HO
- H 2O
O
3
¾ ¾¾
® ( A) ¾¾
® ( B)
H O
D
2
2
Identify ( B ) :
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O
O
O
(a)
(b)
HO
(CH2)5 — CO2H
O
HO
O
O
(d) HO
(CH2)4 — CO2H
HO
(CH2)5 — CO2H
O
(c)
62.
O
(CH2)3 — CO2H
Which of the following is a major product of the reaction shown below?
CH3
Br2
¾¾
¾®
H O
2
(a)
63.
CH3
Br
OH
CH3
OH
Br
(b)
CH3
OH
H
CH3
Br
(c)
(d)
H
Br
OH
H
H
In methyl alcohol solution, bromine reacts with ethylene (ethene) to yield BrCH 2CH 2OCH 3
in addition to 1, 2-dibromoethane because
(a) the methyl alcohol solvates the bromine
(b) the ion formed initially may react with Br - or CH 3OH
(c) this is a free radical reaction
(d) the reaction follows Markovnikov's rule
64.
Which of the following compound was the starting material for the oxidation shown below ?
KMnO
H
+
O
HO
4
? ¾ ¾¾¾¾
®
OH
O
OH
+ CO2
||
O
65.
(a)
(b)
(c)
(d)
Which series of reactions will achieve the following transformation ?
Br
1
2
¾¾
® ¾¾
®
1
(a) Cl 2 CCl 4
(c) Cl 2 CCl 4
2
Br 2
NBS/hv
Cl
Cl
1
(b) HBr
(d) NBS/hv
2
Cl 2 CCl 4
Cl 2 CCl 4
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206
66.
Taking into account the stability of various cycloalkanes and carbocations, as well as the
rules governing mechanisms of carbocation rearrangements, what is the most likely product
of this reaction ?
H–I
¾® ?
I
I
(a)
(b)
I
I
(c)
67.
(d)
A triene is treated with ozone followed by zinc in acetic acid to give the following three
products. What is the structure of the triene ?
O
Products = H
O
O
H
H
H
O
68.
(a)
(b)
(c)
(d)
H
O
H
O
Which of the following compound would yield trialkylborane shown below when treated
with BH 3 THF ?
B
(a) 2-methylbut-1-ene
(c) 3-methylbut-1-ene
69.
(b) 2-methylbut-2-ene
(d) 3-methylbut-1-yne
If the following compound is treated with Pd/C in excess of hydrogen gas, how many
stereoisomers of the product will be obtained ?
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207
(a) 1
(c) 3
70.
(b) 2
(d) 4
Which is the most precise designation of stereochemistry for the products formed in the
electrophilic addition of DBr to 1-methylcyclohexene ? (D = 2H, an isotope of hydrogen)
Br
Br
CH3
(a)
CH3
(b)
D
D
Br
CH3
(c)
(d) both (a) and (b)
H
71.
Consider the addition of HBr to 3,3-Dimethyl-1-butene shown below. What is the best
mechanistic explanation for the formation of the observed product ?
CH3
|
CH3 — C — CH == CH2
|
CH3
H
HBr
H3C
C
H3C
CH3
CH3
C
Br
(a) Protonation of the alkene followed by a hydride shift and addition of bromide to the
carbocation
(b) Double bond shift in the alkene following by the protonation and addition of bromide to
the carbocation
(c) Addition of bromide to the alkene followed by a double bond shift and protonation
(d) Protonation of the alkene followed by a methyl shift and addition of bromide to the
carbocation
72.
Propene CH 3CH == CH 2 can be converted into 1-propanol by oxidation. Indicate which sets
of reagents amongst the following is ideal to effect the above conversion ?
(a) KMnO 4 (alkaline)
(b) Osmium tetroxide (OsO 4 CH 2Cl 2 )
(c) B 2H 6 and alk. H 2O 2
(d) O 3 Zn
73.
Which is the most suitable reagent among the following distinguish compound (3) from the
others ?
(1) CH 3C ºº C — CH 3
(2) CH 3CH 2 — CH 2 — CH 3
(3) CH 3CH 2C ºº CH
(4) CH 3CH == CH 2
(a) Bromine in carbon tetrachloride
(b) Bromine in acetic acid solution
(c) Alk. KMnO 4
(d) Ammonical silver nitrate
74.
The principal organic product formed in the reaction given below is :
peroxide
® ....
CH 2 == CH(CH 2 ) 8 COOH + HBr ¾ ¾¾¾
(a) CH 3 — CHBr(CH 2 ) 8 COOH
(c) CH 2BrCH 2(CH 2 ) 8 COOH
(b) CH 2 == CH(CH 2 ) 8 COBr
(d) CH 2 == CH(CH 2 ) 7 CHBrCOOH
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75.
When 2-butyne is treated with H 2 /Pd – BaSO 4 ; the product formed will be :
(a) cis-2-butene
(b) trans-2-butene
(c) 1-butene
(d) 2-hydroxy butane
76.
In the reaction, CH 3C ºº C — CH 3 ¾ (ii)
¾¾¾
¾® CH 3 — C — C — CH 3 , X is :
Zn H 2O
|| ||
O O
(a) HNO 3
(b) O 2
(c) O 3
(d) KMnO 4
77.
Which of the following alkene on catalytic hydrogenation given cis and trans-isomer ?
(i) X
(a) H2C
(b) H3C
CH3
CH3
CH3
H
(c)
CH3
(d) all of these
H
CH3
78.
In the reaction of hydrogen bromide with an alkene (in the absence of peroxides), the first
step of the reaction is the ................. to the alkene.
(a) fast addition of an electrophilic
(b) slow addition of an electrophile
(c) fast addition of a nucleophilic
(d) slow addition of a nucleophile
79.
Which of the following alcohols cannot be prepared from hydration of an alkene ?
OH
(a)
(b)
OH
OH
(c)
80.
OH
(d)
Which of the species shown below is the most stable form of the intermediate in the
electrophilic addition of Cl 2 in water to cyclohexene to form a halohydrin ?
H
(a)
+
+
OH
(b)
Cl
H
H
+
(c)
(d)
Cl
Cl
81.
H
·
·
The reaction, (CH 3 ) 2 C == CH 2 + Br ¾® (CH 3 ) 2 C - CH 2Br
is an example of a/an ................ step in a radical chain reaction.
(a) initiation
(b) termination
(c) propagation
(d) heterolytic cleavage
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82.
Which of the following most accurately describes the first step in the reaction of hydrogen
chloride with 1-butene ?
(a) Cl – H
¾®
+Cl•
(b) Cl – H
¾®
(c) Cl – H
¾® +
(d) H – Cl
¾® Cl
+
+ Cl–
+Cl–
+
83.
+H–
Which of the following best describes the flow of electrons in the acid-catalyzed dimerization
of (CH 3 ) 2 C = CH 2 ?
CH3
CH3
CH3
H3C
+
H2C == C
(a)
(b)
C ==CH2
C
H2C == C
H3C
CH3
CH3
H3C
H2C
CH3
C — CH2
H2C == C
H3C
CH3
(c)
CH3
CH3
H3C
(d)
C == CH2
+
H2C — C
CH3
H3C
84.
Hydroboration of 1-methylcyclopentene using B 2 D 6 , followed by treatment with alkaline
hydrogen peroxide, gives
Me
Me
D
D
(a)
OH
H
85.
HOOC
Me
COOH
(b)
OH
(c)
H
OH
Br2
¾CCl
¾
¾®
4
(P)
Me
D
H
OH
(d)
H
D
HOOCCH(Br)CH(Br)COOH
(X)
Br
HOOC
(Q)
2
COOH ¾ ¾
¾
® HOOCCH(Br)CH(Br)COOH
CCl
4
(Y)
The correct statements with respect to the above pair of reactions are that
(I) the reactions are stereospecific
(II) (X) is erythro and (Y) is threoisomer
(III) (X) is threo and (Y) is erythro isomer
(IV) each of (P) and (Q) gives a mixture of (X) and (Y)
(a) I and II
(b) I and III
(c) I and IV
(d) II and IV
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86.
The products P and Q in the following sequence of reactions, are
MeO
(i) O 3 (1equiv.)
Li, EtOH
3 l
¾® Q
¾ ¾¾¾
¾® P ¾ ¾¾¾¾¾¾¾
NH ( )
Me
MeO
(ii) -78°C, MeH Me2S
MeO
MeO2C
(a)
Me
MeO
MeO
(b)
OHC
Me
Me
MeO
CHO
COMe
(c)
87.
MeO
COMe
CHO
MeO2C
OHC
Me
(d)
Me
Me
4-Pentenoic acid when treated with I 2 and NaHCO 3 gives :
(a) 4, 5-diiodopentanoic acid
(b) 5-iodomethyl-dihydrofuran-2-one
(c) 5-iodo-tetrahydropyran-2-one
(d) 4-pentenolyiodide
OH
H SO , 0°C
2
4
¾ ¾¾¾¾
® ( A) ¾ ¾¾® ( B ); Product (B) of the reaction is:
H O
88.
- HCl
2
Cl
O (b)
(a)
O (c)
O (d)
O
CH = CH2
Br
(i) NaNH
(i) alc.KOH
(ii) NaNH 2
2
2
¾
® (C) , Product (C) is :
¾CCl
¾
¾
® (A) ¾ ¾¾¾¾® (B) ¾ ¾¾¾
89.
4
(ii) CH 3 -Cl
(Styrene)
(a) Ph — C ºº CNa
(c) Ph — C ºº C — CH 3
90.
Which of the following will give a mixture of cis and trans-1,4-dimethyl cyclohexane, when
undergo catalytic hydrogenation ?
CH2
|
(a)
(b)
|
CH3
91.
(b) Ph — CH 2 — C ºº CH
(d) Ph — CH == C == CH 2
(c)
(d) both (a) & (b)
|
Cis-3-6 dimethyl
cyclohexene
An optically active compound A with molecular formula C 8 H 14 undergoes catalytic
hydrogenation to give meso compound, the structure of (A) is :
CH3
CH3
CH2 – CH3
(a)
(b)
(c)
CH3
CH3
CH3
(d)
CH3
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CH3 — CH2
CH2– CH3
C == C
92.
CH3
+ HBr ¾ ¾¾¾¾® Products
R 2O 2
(Per- oxide)
CH3
How many products will be formed in above reaction ?
(a) 2
(b) 4
(c) 3
(d) 6
H
C == C
93.
2
¾¾
¾
® Product of the reacion is :
Pt
D
CH3
(a) Racemic
(c) Meso
94.
(b) Diastereomers
(d) Pure enantiomers
HBr
Peroxide
cis-2-butene ¾ ¾¾¾® product ; Product of the reaction is :
(a) Racemic
(c) Meso
CH3
(b) Diastereomer
(d) E and Z isomer
H
H
CH3
95.
(a)
96.
(b)
Rate of reaction towards reduction using (H 2 Pt) :
(a) a > b
(b) a = b
(c) b > a
(d) Reduction of given molecule is not possible
O
O
R'
R
||
CH 3 -S -CH 3
C
C
¾® Product A + CH 3 — S — CH 3
R ¾ ¾¾¾¾
H
dimethyl sulfide
O
O
Product A of the above reaction is :
O
||
(a) R — C — R
(b) R¢ — CHO
(c) R — CO 2 H
(d) both (a) and (b)
O
C
—O—O—H
(MCPBA)
97.
CH3
CH3
C == C
H
H
Cl
CH2Cl2
Product; Product is :
MCPBA ¾® Metachloroperbenzoic acid
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(a)
CH3
H
C— C
H
O
H
C— C
(c)
CH3
CH3
CH3
H
CH3
(d)
C–C
H
H
CH3
H
CH3
CH3
O
(b)
H
OH
CH3
OH
H
(c)
OH
CH3
H
H
(d)
H
H
CH3
(1) THF : BD
3
CH 3 — CH == CH 2 ¾ ¾¾¾¾¾
® (A) ; Product ( A) of the above reaction is:
( 2)CH 3CO 2T
(a) CH 3 — CHD — CH 2 D
(c) CH 3 — CHD — CH 2 T
(b) CH 3 — CHT — CH 2 T
(d) CH 3 — CHT — CH 2 D
Optically active isomer (A) of (C 5 H 9 Cl) on treatment with one mole of H 2 gives an optically
inactive compound (B) compound (A) will be :
(a) CH 3 — CH — CH == CH 2
(b) Cl — CH — CH == CH — CH 3
|
|
CH
CH 2Cl
3
(c) CH 3 — CH — CH 2 — CH == CH 2
(d) CH 3 — CH 2 — CH — CH == CH 2
|
|
Cl
Cl
An organic compound C 4 H 6 on ozonolysis give HCHO, CO 2 , CH 3 CHO. Compound will be :
(a) H 2 C == CH — CH == CH 2
(b) CH 3 — CH == C == CH 2
(c) CH 3 — C ºº C — CH 3
(d)
HCHO, H +
H 2O
102.
¾ ¾¾¾¾® major product of this reaction is :
(a)
OH
(b)
OH
(c)
OH
103.
H
(2) H 2O 2, HO -
(a)
101.
O
CH3
H
CH3
100.
C— C
H
CH3
O
CH3
(1) BH 3 ; THF
¾ ¾¾¾¾
¾® (A) ; Product of the reaction is :
98.
99.
(b)
OH
CH 3
|
KMnO 4
HBr
H+
® ( A) ¾ ¾
¾® (B) ¾ ¾¾
¾® (C)
CH 3 — CH ¾ ¾¾¾
ROOR
D
|
CH 3
CH2 – OH
OH
(d)
OH
OH
Product (C) in the above reactions is :
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CH 3
|
(b) CH 3 — C — Br
|
CH 3
CH 3
|
(d) CH 3 — CH
|
CH 2 - Br
H
|
(a) CH 3 — C — Br
|
CH 3
(c) CH 3 — CH — H
|
CH 2 -Br
104.
105.
CH 3
|
HF
CH 3 — C == CH 2 + (CH 3 ) 2 CHCH 3 ¾ ¾¾® C 8 H 18 ( A)
273K
Unknown (A) in the above reaction is :
(a) 2, 2, 3-trimethyl pentane
(c) 2, 2-dimethyl hexane
OH
Br2
MeOH
¾¾
¾® HBr + (P) ¾ ¾¾
¾® (Q)
Cl
O
Cl
(a)
CH3O
O
||
(c) CH 3 - C - OMe
(b) 2, 2, 4-trimethyl pentane
(d) n-octane
; Product (Q) is :
O
(b) Br
OMe
O
(d)
H+
cold dil.
D
KMnO 4
OMe
CH3
CrO
3
¾¾
¾® ( A) ¾ ¾¾¾® ( B ) ¾ ¾¾
® (C)
106.
OH
Product (C) of the reaction is:
O
(a)
(b)
(c)
O
107.
OH
O
(d)
O
O
CHO
What is the major product expected from the following reaction ?
CH3
D - Cl
¾ ¾¾
¾® Product
CH3
CH3
(a)
H
(b)
D
H
(c)
H
Cl
Cl
H
D
D
(d)
Cl
CH3
CH3
Cl
H
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214
108.
Choose the correct product of this reaction :
1. Br
2
¾ ¾¾
®
2.H 2O
CH2 –CH3
Br
(a)
CH2 –CH3
OH
(b)
H
Br
Br
OH
(c)
(d)
Br
H
H
Br
CH3
1. BH 3 /THF
¾ ¾¾¾¾¾
® A; Product A is:
–
109.
2. H 2O 2 /OH
CH3
CH3
H
H
(a)
(b)
CH3
H
CH3
OH
(c)
(d)
OH
H
OH
OH
CH3
1. Hg(OAc) ,H O
2 2
¾ ¾¾¾¾¾
¾® Product; Product is :
110.
2. NaBH 4
CH3
H
H
(a)
CH3
CH3
(b)
OH
(c)
CH3
OH
H
(d)
CH3
OH
OH
111.
H
Choose the correct product of the following reactions :
O
CH3
CH3
OH
CH3
(a)
CH3
H
112.
Cl
OOH
1.
2.
H3O+
CH3
(b)
OH
OH
CH3
CH3
OH
(c)
CH3
OH
(d)
OH
CH3
H
CH3
How many stereoisomeric tetrabromides will be formed in the following reaction ?
2Br2
¾¾¾¾®
CCl 4
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215
(a) 2
113.
(b) 3
(c) 4
(d) 6
How many stereoisomeric pentabromides will be formed in the following reaction ?
Br
2Br2
¾¾¾¾®
CCl 4
(a) 2
(c) 4
(b) 3
(d) None of these
HCl
peroxide
114.
EtONa
¾ ¾¾¾® (A) ¾ ¾¾
¾® (Z) (major)
D
Identify (Z) in the above sequence of reactions :
(a)
(b)
O
(c)
115.
(d)
CH3
OEt
CH 3 — CH — CO 2 K
electrolysis
|
¾ ¾¾¾¾® (A) (Major)
CH 3 — CH — CO 2 K
Major product (A) of the above reaction :
(a)
(b)
(c)
(d)
O
O
116.
CH == CH2
O
O
CF3CO3H
(A)
(B)
O
(only one enantiomer is taken)
Which of the following statement is correct about A and B ?
(a) A and B are mixture of diastereomers
(b) A and B are mixture of enantiomers
(c) A and B are optically active
(d) B is racemic mixture
CH3
117.
CH3O
NaBH
O
O
H O
4
3
¾ ¾¾¾
® A ¾¾
¾
® B ¾ ¾2¾® (C) (one of the product)
H
HO O
Identify the product (C):
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O O
|| ||
(a) CH 3 — C — C — O — CH 3
CH 2 — OH
|
(b) CH — OH
|
CH 2 — OH
CHO
|
(c) CH — OH
|
CH 2 — OH
CHO
CHO
|
(d) CHOH
|
CHO
Å
CH =CH - P Ph Br s
HO Q
2
3
¾ ¾¾® (X) ¾ ¾¾¾¾¾¾
¾® (Y)
118.
OH
Product (Y) of the above reaction is :
(a)
(b)
O
O
CH == CH — CH2 — OH
CH == CH — CH3
(c)
(d)
CH3
OH
119.
Br
Na / liq.NH
2
3
In the reaction Me — C ºº C — Et ¾ ¾¾¾¾
¾
® P ¾ ¾¾
® (Q) ; then Q is :
CCl 4
(a)
(b)
(c)
(d)
A pure compound which is optically inactive due to internal compensation
A binary mixture which is optically inactive due to external compensation
A binary mixture which is optically active
A pure compound which is optically inactive due to absence of chiral centre
(a)
(b)
(d)
120.
(c)
Which (p-bond) will reduce first, when above compound undergoes catalytic hydrogenation ?
(a) a
(b) b
(c) c
(d) d
121.
Compound A, which is a degradation product of the antibiotic vermiculine has following structure
O
C
CH3
CH
CH
O
||
CH == CH — C
CH2
CH2
C
OCH3
O
( A)
C11 H14O 4
H
2
¾ ¾¾
®
Pd C
( B)
C11 H18O 4
(CH ) S
O
3
3 2
¬¾¾¾
¾ ¬¾¾
¾¾
CH 2Cl 2
(C )
. Unknown (C) is:
C11 H18O 2
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CH2
C
(a) CH3
CH2
CH2
C
CH2
CH2
C
(b) CH3
CH== CH O
C – O – CH3
CH2
CH2
CH2
O
CH2
C
C
CH2
OCH3
CH2
CH2
O
CH2
C
CH2
(c) CH3
CH2
CH2
CH2
C
CH
C
|
CH3
CH2
OCH3
(d) None of these
O
A
122.
O
B
O
Reagent (A) and (B) in above reaction are :
(a) A = RCO 3 H , B = H 2 O 2
(b) A = RCO 3 H , B = HIO 4
(c) A = RCO 3 H, B = O 3
123.
(d) A = O 3 , B = RCO 3 H
Rank the following in the increasing order of rate of reaction with HBr .
(P) O
(R) HN
(Q)
(a) R > P > Q
(c) P > R > S
124.
125.
(b) R > Q > P
(d) P > S > R
Select the reaction(s) that would result in the formation of 2-bromopropane.
peroxide
4
(I) CH 3 CH == CH 2 + HBr ¾ ¾¾¾
(II) CH 3 CH == CH 2 + HBr ¾CCl
®
¾¾
®
hn
(III) CH 3 CH 2 CH 3 + Br 2 ¾ ¾
®
4
(IV) CH 3 CH == CH 2 + Br 2 ¾CCl
¾¾
®
(a) I and III
(c) I, II, and III
(b) II and III
(d) I, II and III
Which of the following reactions generates the major product ? Ignore stereoisomerism.
(a)
+ HBr ¾®
Br
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(b)
(1) Hg(OAc) , H O, THF
2
2
¾ ¾¾¾¾¾¾¾¾
®
(2) NaBH
4
(1) BH 3
(c)
¾ ¾¾¾¾¾¾
¾®
-
(d)
2
2
4
¾ ¾¾¾¾
¾
®
(2) OH , H 2O 2, H 2O
H O, H SO
Br
2
¾¾
¾
®
(e)
126.
OH
OH
OH
Br
CCl 4
Br
In the given selective hydrogenation which combination is incorrect ?
(a)
H
2
¾¾
¾
®
(W.C. = Wilkinsons catalyst)
W.C.
H
W.C.
2
¾¾
¾
®
(b)
H
W.C.
2
¾¾
¾
®
(c)
(d)
(W.C. = Wilkinsons catalyst)
H
D
2
¾¾
¾
® CH 2 — CH == CH — CH 3
1. NaNH2
2. TsO
Na NH ( )
MCPBA
3 l
(A) ¾ ¾¾¾¾
® (B) ¾ ¾¾¾® (C).
127.
Compound (C) in above sequence of reaction is :
H
H
H
(a)
(b)
O
H
O
(c)
C
(d)
O
||
CH2 – C
O
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219
HBr
128.
¾¾¾® ( A) ;
CH3
R 2O 2 / hn
Major product (A) is :
Br
(a)
(b)
CH3
Br
Br
(c)
129.
(d)
In the reaction given below, the product would be :
OH
H O
|
+
3
CH 3 — CH == CH — CH 3 ¾ ¾¾
¾® CH 3 — CH 2 — CH — CH 3
(a) a mixture of diastereomers
(c) optically pure enantiomer
130.
(b) optically active
(d) a racemic mixture
Surprisingly, the reaction shown below goes through classical carbocation. What is the major
product of this reaction ?
Br
+ HBr ¾®
(a) trans-1, 3-dibromocyclohexane
(c) trans-1, 2-dibromocyclohexane
131.
(b) cis-1, 3-dibromocyclohexane
(d) cis-1, 2-dibromocyclohexane
The major product of the reaction given below is :
Br2
OH ¾ ¾
¾® ?
H 2O
OH
(i) Br
OH
OH
(ii) Br
Br
(iii) HO
O
(v)
Br
OH
(iv) HO
H
CH2Br
(a) (i) and (ii)
(c) (v) and (vi)
OH
O
(vi)
OH
CH2Br
H
(b) (iii) and (iv)
(d) none of these
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132.
Which reaction will occur at the fastest rate ?
Br
HBr
(a)
HBr
(b)
Br
Br
HBr
(c)
HBr
(d)
Br
Cl
Na
dry ether
¾¾¾®
133.
134.
Above reaction is known as :
(a) Wurtz reaction
(c) Fittig reaction
O
||
Red P + HI
CH 3 ¾ CH 2 ¾ C ¾ H ¾¾¾¾® A
Product A is :
(a) propane
135.
(b) propanol
(c) prapanoic acid
(d) propene
Which of the following compound give diastereomers when treated with Br 2 in CCl 4 ?
(a)
136.
(b) Wurtz fittig reaction
(d) Kolbe electrolysis
(b)
(c)
CH2
CH3
Methylcyclopentane
1-Methylcyclopentene
(d)
H
CH3
3-Methylcyclopentene
H
CH3
4-Methylcyclopentene
A mixture of C 2 H 6 , C 2 H 4 and C 2 H 2 is bubbled through alkaline solution of copper (I)
chloride, contained in Woulf’s bottle. The gas coming out is :
(a) original mixture
(b) C 2 H 6
(c) C 2 H 6 and C 2 H 4 mixture
(d) C 2 H 4 and C 2 H 2
+
Br CCl
H
2
4
¾¾
® Possible products ¾ ¾¾¾
® ( y) products
137.
D
OH
(x)
The number of possible products for x and y is :
(a) 2, 4
(b) 3, 5
(c) 3, 6
(d) 3, 4
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138.
Select the incorrect statement :
(a) Bromine is more selective and less reactive
(b) Chlorine is less selective and more reactive
(c) Benzyl free radical is more stable than 2° free radical
(d) Vinyl free radical more stable than allyl free radical
139.
Which of the following compound does not evolve CO 2 gas, when undergo oxidative
ozonolysis ?
140.
(a)
(b)
(c) H 2 C == CH — CH == CH 2
(d)
a)
cis-3-hexene ¾(¾
¾® meso 3,4-hexanediol
b)
trans-3-hexene ¾(¾
¾® meso 3,4-hexanediol.
Choose pair of reagent ( a , b) for above conversions.
(a) Cold KMnO 4 ,OsO 4
(b) Cold KMnO 4 , RCO 3 H H 3 O Å
(c) RCO 3 H H 3 O Å , cold KMnO 4
(d) None of these
Na
Liq. NH 3
O
Zn
Product (C) of the above reaction is :
(a) 1,3-hexadiene
(c) 1,3-butadiene
142.
Ph P ==CH (2mole)
3
3
2
¾ ¾¾¾® ( A) ¾ ¾
¾
® ( B ) ¾ ¾¾
¾¾¾¾
¾® (C )
141.
(b) 1,4-pentadiene
(d) 1,3-heptadiene
How many carbon-hydrogen bond orbitals are available for overlap with the vacant p-orbital
in ethyl carbocation ?
(a) 0
(b) 3
(c) 5
(d) 6
143.
To achieve above conversion, the reagents used will be :
(a) O 3 H 2 O 2 , HO - D
(b) HBr, alc. KOH, O 3 ,LiAlH 4 ,H + D
(c) HBr, t-BuOK, O 3 , KMnO 4 , D
(d) HCl, KMnO 4 (cold), H + D
O
144.
Hg(OAc)
2
¾ ¾¾¾
¾
® X (major); Product ( X ) is:
AcOH
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222
O
O
O
(a)
O
(b)
(c)
OH
OAc
HgOAc
145.
(d)
H
HgOAc
OAc
OH
Decreasing order of heat evolved upon catalytic hydrogenation of given reactants with a H 2
(Pd/C) is :
(a)
(b)
(a) b > c > a > d
(c)
(b) d > a > c > b
(d)
(c) d > c > a > b
(d) c > b > c > d
146.
(a)
(b)
(c)
(d)
The correct order of heat of hydrogenation of given molecules is :
(a) d > c > a > b
(b) d > c > b > a
(c) b > a > c > d
(d) d > a > c > b
147.
OH
1. Hg(OAc)2
A
2. NaBH4
Product (A) of the above reaction is :
O
O
(a)
O
O
(b)
(c)
(d)
CH3
CH2
+ HBr
C
148.
A
(Major)
Product (A) is :
(a)
Br
(b)
Br
Br
Br
(c)
(d)
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223
HBr
CCl 4
149.
¾ ¾¾® Product; Comment upon optical activity of the product.
(a)
(b)
(c)
(d)
Racemic mixture
Diastereomers
Meso
Optically inactive due to absence of chiral center
CH 3
|
150.
Hg(OAc) /EtOH
2
CH 3 — C == CH — CH 3 ¾ ¾¾¾¾¾
¾® ( A)
( 90%)
Product (A) of the above reaction is :
CH 3
CH 3
|
|
(b) CH 3 — C — CH — CH 3
(a) CH 3 — C — CH — CH 3
|
|
|
OEt HgOAc
CH 3
CH 3
|
|
(c) CH 3 — C — CH — CH 3
|
OH
151.
|
HgOAc OEt
(d) CH 3 — C — CH — CH 3
|
|
HgOAc
|
HgOAc OH
Al O
(i) HI
(ii) AgOH
2 3
Me 2 CH — CH — Me ¾ 350
¾¾
¾
®( A) ¾ ¾¾® ( B )
°C
|
OH
Product (B) of above reaction :
(a) Me 2 C(OH)CH 2 Me
152.
(b) Me 2 CH — CH — Me
|
OH
(d) HO — CH 2 — (CH 2 )Me
(c) Me — CH — CMe 3
|
OH
In which of the following reaction, Markownikoff's rule is violated ?
HBr
CCl 4
(a) CH 3 — O — CH == CH 2 ¾ ¾¾®
HBr
CCl 4
(c) CH 3 — S — CH == CH 2 ¾ ¾¾®
153.
HBr
CCl 4
(b) CH 3 — NH — CH == CH 2 ¾ ¾¾®
HBr
CCl 4
(d) O 2 N — CH == CH 2 ¾ ¾¾®
Decreasing order of rate of reaction of molecules towards electrophilic addition reaction is :
CH == CH2
CH == CH2
CH == CH2
CH == CH2
NO2
OH
CH3
(a)
(b)
(c)
NH2
(d)
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224
(a) a > b > c > d
(c) d > b > c > a
154.
(b) b > c > a > d
(d) b > d > c > a
H - A (acid)
2 CH 3 — C == CH 2 ¾ ¾¾¾¾® ( A)
|
(major)
Ph
Product (A) is :
Ph
(a)
(b)
Ph
Ph
(c)
(d)
CH3
Ph
H+
155.
O
CH2 — OH
Ph
ROH
¾¾
¾
® ( A) ¾ ¾¾
® ( B)
Å
D
H
(major)
Product (B) of the above reaction is :
OR
(a)
(b)
O
O
OR
O
O
OR
(c)
(d)
O
156.
OR
Which of the following compounds gives the same carbocation on ionization ?
Br
Br
Br
Br
1
(a) 1 and 3
(c) 1 and 2
157.
2
3
(b) 2 and 4
(d) 1 and 4
4
For the following reactions the major products are shown :
HBr
+ 25°C
H 2 C == CH — CH == CH 2 ¾¾¾® H 2 C == CH — CH — CH 3 ¾¾® CH 2 CH == CHCH 3
0°C
|
|
Br
Br
1
2
control at
control at low temperature and ¾¾¾
These provide an example of ¾¾¾
higher temperature.
1
2
1
2
(a) kinetic
thermodynamic
(b) thermodynamic
kinetic
(c) kinetic
kinetic
(d) thermodynamic thermodynamic
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225
158.
What is the product of 1, 4-addition in the reaction shown below ?
HCl
(a)
(c)
159.
160.
(b)
Cl
(d)
Cl
CH3
Cl
Cl
H
H
OH
Dehydration of the above compound will give :
(a) meso product
(b) racemic mixture
(c) diastereomer
(d) optically pure enantiomer
CH2 - CH3
H
Cl
HBr
¾CCl
¾¾®
4
CH = CH2
What is stereochemistry of product ?
(a) Racemic mixture
(c) Diastereomers
H
A
CH3
O
H2
OH
161.
(b) Optically inactive
(d) Meso product
End product formed in the above reaction is :
(a) Optically active (b) Racemic
(c) Meso
162.
(d) Diastereomer
How many moles of BH 3 are needed to react completely with 2 mole of 1-pentene in
hydroboration-oxidation reaction ?
(a) 2 mole
(b) 3 mole
(c) 2 3 mole
(d) 3 2 mole
OCH3
Li
Liq. NH3
163.
A
H3O+
B
Product (B) in the above reaction is :
O
O
OH
OCH3
(a)
(b)
(c)
(d)
OH
OCH3
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14
164.
low conc. of Br
2
® ( ?)
H 2C == CH — CH 3 ¾ ¾¾¾¾¾
or high temp
Product of the above reaction is :
14
14
(a) H 2 C == CH — CH 2 — Br
(b) H 2C == C H — CH 2 — Br
14
(c) CH 2 — CH — CH 3
|
Br
165.
(d) both (a) and (b)
|
Br
In which of the following reactions 1,3-butadiene will be obtained as a major product ?
(CH 3 )3 COK (2mole)
(a) Br — CH 2 — CH 2 — CH 2 — CH 2 — Br ¾ ¾¾¾¾¾¾
®
(CH 3 )3 COH
Conc. H 2SO 4
(b) HO — CH 2 — CH 2 — CH 2 — CH 2 — OH ¾ ¾¾¾¾®
H (1mole)
2
(c) H 2C == CH — C ºº CH ¾ ¾¾¾
¾®
Ni B
2
166.
(d) All of these
CH3
H2C
C
CH3
CH3
(a) CH3
C
Cl2
1. H2O
H+
2. Ca(OH)2
20°C
CH2
D
A ; Identify A.
(b) CH 3 - CH - CHO
|
O
CH 3
CH 3
O
|
||
(c) CH 3 — C — CH 2 — CH 3
H2SO4
167.
D
(d) CH 3 — C == CH 2
A;
OH
Product (A) is :
(a)
(b)
(c)
(d)
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CH3
168.
d
c
NBS
A (major)
b
a
CH3
H
Bromination take place at :
(a) a
(b) b
169.
(c) c
(d) d
Which is incorrect statement about heats of combustion ?
>
(a)
>
(b)
>
>
(c) Iso-butene > trans-2-butene > 1-butene (d) n-Hexane < n-Heptane < n-Octane
170.
Predict the major product of the reaction.
O
CH 3
|
CH 3 — C == C — CH 2 — CH == CH 2
|
CH3
CH 3 CH 3
|
Cl
COOH
(Product)
H+
CH 3
|
|
CH 3
|
(a) CH 3 — C == C — CH 2 — CH — CH 2 (b) CH 3 — C — C — CH 2 — CH == CH 2
O
O
CH 3 CH 3
|
|
(d) CH 3 — C — C — CH 2 — CH == CH 2
|
|
OH OH
CH 3 CH 3
|
|
(c) CH 3 — C == C — CH 2 — CH — CH 2
|
OH
cold dil. KMnO
4
¾ ¾¾¾¾¾
¾
® Product of the reaction is:
171.
(a) Meso compound
(c) Diastereomers
O
H
CH3O
(b) Enantiomeric pair
(d) Optically pure enantiomer
H
C
H
H
C
C
C
C
C
C
C
C
H
H
H
H
H
HO – C
172.
|
OH
H
H
H
H
H
H
O3 (dichloromethane)
(CH3)2S
(A)
+
Optically active
(B)
Optically inactive
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228
Product (A) of above reaction is:
(a) CH 3 O — CH — CH 2 — CH 2 — CHO
|
CO 2H
CO 2H
|
(b) CH 3 O — CH 2 — CH — CH 2 — CO 2 H
(c) CH 3 O — CH — CH 2 — CH 2 — CO 2 H
|
CO 2H
(d) CH 3 O — CH — CH 2 — CH 2 — CH 2 — CHO
|
CO 2H
O
H (2- 3atm)(1 mole)
¾ ¾2 ¾ ¾ ¾ ¾ ¾
¾® Products ; Comment up on optical activity of products.
173.
10% Pd C
(a) Diastereomers
O
(b) Racemic mixture (c) Meso
+ HBr
174.
(d) Optically pure enantiomer
¾¾® Product
(1 mole)
Addition of a mineral acid to an olefin bond leads to major product, Identify it:
O
Br
O
(a)
(b)
Br
O
Br
O
(c)
(d)
Br
175.
H2 (one mole)
PtO2
Product
In polyenes that contain differently substituted (C==C) double bonds, it is possible to
hydrogenate chemeselectively one (C==C) double bond. Product is :
(a)
(b)
(c)
(d)
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229
MCPBA
176.
OH
Product
(MCPBA ¾® meta-chloro perbenzoic acid)
Stereochemistry of the product of above reaction is :
(a) Meso
(b) Racemic
(c) Diastereomers
(d) Optically inactive due to absence of chiral center.
O
Conc. H2SO4
177.
P
Identify product (P).
O
(a)
O
(b)
(c)
O
(d)
O
H2SO4
B
178.
A
A isomerise to B on addition of traces of acid H 2 SO 4 . Compound (B) is :
(a)
R
179.
(b)
(c)
(d)
OH
SOCl2
pyridine, D
A
Product (A) of the reaction is :
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230
Cl
R
R
R
(a)
(b)
(c)
(d) None of these
OH
180.
HO
H + (excess)
D
¾ ¾ ¾ ¾¾®( A). Product (A) is :
OH
(a)
181.
(b)
(c)
(d)
Which of the following reactions do not represent the major product of given Birch reductions ?
Na
liq. NH3
(i)
CH3
(iii)
Na
liq. NH3
(ii)
CH3
Na
liq. NH3
CO2H
(iv)
CO2H
Na
liq. NH3
Na
liq. NH3
(v)
Na
liq. NH3
(vi)
Na
liq. NH 3
(vii) 2-butyne ¾ ¾ ¾¾® cis-2-butene
(a) (i), (iii), (vi)
(c) (iv), (v), (vi)
BH
(b) (iv), (vi), (vii)
(d) (i), (ii), (v), (vii)
H O , HO -
3
2
¾ ¾¾
® ¾ ¾2 ¾
¾¾® ( A)
182.
OR
Product (A) is:
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231
OH
OH
(a)
(b)
OH (d)
OH(c)
OR
OR
OR
OR
OH
Hint : Think carefully about the relative stabilization of developing positive charge, when the double bond reacts
with an electrophile.
NaOH,
H 2O
25°C
HOCl
183.
¾ ¾¾® ( A) ¾ ¾ ¾
¾® ( B )
70%
Correct statement about above reaction is:
(a) A = cis-2-chlorocyclohexanol,
(b) A = trans-2-chloro cyclohexanol,
(c) A = trans-2-chlorocyclohexanol,
(d) A = cis-2-chlorocyclohexanol,
B
B
B
B
= cyclohexeneoxide
= anti-diol
= cyclohexeneoxide
= anti-diol
Å
H
¾ ¾¾® Predict the major product:
184.
HO
O
(a)
(b)
(c)
(d)
HO
HO
O
H SO
4
¾ ¾2 ¾
¾
® ( A) ; Product (A) is :
185.
( Major )
(a)
OH
OH
OH
(b)
(c)
(d)
Br
82
186.
Br -
82
Br ¾ ¾¾® Major product of the reaction is :
CCl 4
H
Br82
Br
(a)
H
Br82
Br82
(b)
Br
H
Br82
Br82
(c)
Br82
H
Br
Br82
Br82
(d)
H
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232
Br2
CCl4
187.
stereochemistry of the product is:
H CH3
(a) Diastereomers
(c) Meso
Br2
CCl4
188.
(b) Racemic mixture
(d) Pure Enantiomers
Product/s obtained is/are :
H CH3
(a) Diastereomers
(c) Meso
(b) Racemic
(d) Optically pure enantiomers
Ph P =CH
Ph P =CH
2
2
¾ ¾3¾ ¾
¾
® ¾ ¾3¾ ¾
¾
® ( x) ; Product ( x) is :
189.
O
(a)
(b)
CH2
(c)
(d)
CH–CH3
CH 3
|
190.
H+
CH 3 — CH 2 — CH 2 — CH 2 — C — CH 2 — OH ¾ ¾
¾
® ( A) ; Product (A) is :
D
|
(major)
CH 3
(a) CH 3 — CH 2 — CH 2 — CH 2 — C == CH — CH 3
|
CH 3
(b) CH3—CH2—CH2—CH2—CH == C
CH3
CH3
(c) CH 3 — CH 2 — CH 2 — CH 2 — C == CH 2
|
CH 3
CH 3
|
(d) CH 3 — CH 2 — CH — CH 2 — C == CH 2
|
CH 3
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233
191.
CH 3 — CH == CH — CH 3
HBr
R 2O 2, D
(Anti - Markownikoff's addition)
¾ ¾ ¾¾®
Comment on optical activity of the products:
(a) Racemic
(b) Diastereomer
(c) Meso
(d) Optically pure enantiomer
O
||
CH -C -O -O - H
¾ ¾3¾ ¾ ¾ ¾® ( A) ; Product (A) is :
192.
( major )
OH
OH
O
O (b)
(a)
Racemic mixture
H2O
A
(alkene)
194.
(d)
OH
OH
RCO3H
193.
(c)
Cold dil. KMnO4
Meso-compound
Alkene (A) will be :
(a) cis-2-pentene
(b) cis-2-hexene
(c) cis-4-octene
(d) trans-2-hexene
O
+ PPh 3 ¾® ( A) + POPh 3
(major)
H
Me
Me
H
Product (A) is
(a) trans-2-butane
195.
(b) cis-2-butene
(c) 1-butene
(d) Iso-butene
In which of the following reactions, two products will be formed other than phosphonium
ylide (POPh 3 )
O
(a)
+ Ph 3 P == CH 2 ¾®
(b) CH 3 CHO + Ph 3 P == C — CH 3 ¾®
|
CH 3
O
O
||
||
(c) Ph — C — H + Ph 3 P == CH — Ph ¾®
(d) H — C — H + Ph 3 P == CH — CH 3 ¾®
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234
196.
To carry out the given conversions, select the correct option:
O
R1 — C — R2 + R2CO2H
O
a
R1
H
O
O
b
C
C
R2
R2
O
c
R1 — C — R2 + R2 — CHO
OH
R1 — CH — R2 + R2 — CH2 — OH
(a)
(b)
(c)
(d)
197.
a = Ag 2 O,
a = H 2O 2 ,
Both (a) and (b)
None of these
b = Zn CH 3 CO 2 H,
b = CH 3 - S - CH 3 ,
c = LiAlH 4
c = NaBH 4
The product (A) of given alkoxymercuration de-mercuration is :
CH3
(1) Hg(O CCF ) , CH OH
3
¾ ¾ ¾ ¾2 ¾3¾2 ¾ ¾
¾® ( A)
(2) NaBH 4 , HO -
(major)
OCH3
OCH3
(a)
(b)
OH
(c)
OH
(d)
ONa
|
198.
H+
HC ººCH
H2
Al O
3
CH 3 — C == CH 2 ¾ ¾ ¾ ¾
¾
®
¾® ¾ ¾¾® ¾ ¾ ¾ ¾¾® ¾ ¾2¾
Pd- BaSO 4
D
End product of the reaction is :
(a) H 2 C == CH — C == CH 2
(b) CH 3 — CH == CH — CH == CH 2
|
CH 3
(c) H 2 C == CH — CH == CH 2
199.
(d) H 2 C == CH — CH 2 — CH == CH 2
Major product of the given reaction is :
HI(excess)
H 2 C == CH — CH 2 — I ¾ ¾CCl
¾¾
¾®
4
(a) CH 3 — CH — CH 2
|
|
I
I
(b) CH 3 — CH — CH 3
|
I
(c) CH 3 — CH 2 — CH 2 — I
(d) I — CH 2 — CdH 2 — CH 2 — I
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235
200.
The rate constant for a reaction can be increased by a the stability of the reactant or by b the
stability of the transition state. Select the correct choice for a and b.
(a) decreasing, decreasing
(b) increasing, decreasing
(c) decreasing, increasing
(d) increasing, increasing
201.
Major product of the given reaction is :
H 2 C == CH 2 +
H+
D
CH2
¾¾
¾® Product
(a)
(b)
CH 3
|
(c)
(d) H 2 C = C -CH 2 - CH 2 - CH 3
O
202.
+ Ph 3 P == CH 2 ¾® ( A)
Major
Major product (A) is :
OH
(a)
203.
(b)
(c)
(d)
In the given reaction, only one alkene undergo preferential oxidation by electrophilic
ozone. Identify product (P) of the given reaction:
OMe
O
¾ ¾ ¾ ¾ ¾3¾ ¾ ¾ ¾® ( P )
Me2S, -78°C then NaBH 4
(a)
CO2Me
CHO
(b)
( > 52%)
CO2Me
OH
O
||
(c) CH 3 — C — CH 2 — CH == C — CH 2 — CHO
|
OH
OMe
|
(d) CH 3 — CH — CH 2 — CH == C — CH 2 — CH 2 — OH
|
OMe
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236
HCl
204.
¾® ( P ) ; Product ( P ) is:
CH2—CH2—CH == CH2 ¾ ¾
(major)
OH
Cl
Cl
Cl
(a)
(b)
(c)
(d)
2
CO2H ¾ ¾ I¾¾
® ( A) ; Major product of the reaction is :
205.
NaHCO 3
I
O
(a)
(b)
O
O
O
I
I
(c)
O
(d)
O
O
O
OH
H
Å
H O
OMe ¾ ¾ ¾2 ¾
¾® ( A) ¾ ¾3 ¾® ( B )
206.
Pd - BaSO 4
Product (B) is :
OH
O
|
207.
||
(a) Ph - CH - CH = CH - CH 2 - C - H
(b) Ph - CH = CH - CHO
(c) Ph - (CH = CH) 2 - CHO
(d) Ph - (CH = CH) 3 - CHO
Isobutene, in the presence of H 2 SO 4 , forms a mixture of two isomeric alkene (C 8 H 16 ). The
major alkene is :
CH 3
CH 3
|
|
(a) CH 3 — C — CH == C — CH 3
|
CH 3
CH 3
|
CH 3
CH 3
|
|
(b) CH 3 — C — CH 2 — C == CH 2
|
CH 3
CH 3
CH 3
|
(c) CH 3 — CH — CH == CH — CH — CH 3
|
CH 3
|
(d) CH 2 == C — CH 2 — CH 2 — CH — CH 3
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237
208.
An unknown alkene (A) reacts with 3 mole of H 2 gas in presence of platinum catalyst to form
1-isopropyl-4-methyl cyclohexane. When unknown alkene (A) is ozonized and reduced,
following product are obtained
O
O
O
O
O
O
||
||
H — C — H,
||
||
||
H — C — CH 2 — C — C — CH 3 ,
||
CH 3 — C — CH 2 — C — H
The alkene (A) is :
(a)
(b)
(1) NBS
(c)
(d)
O
||
CH 3
H— C —CH /
\
CH 3
OsO 4
¾ ¾¾¾¾¾® ( A) ¾¾¾¾¾¾¾® (B) ¾ ¾¾
® (C )
H O
209.
(2) Mg ether
CH 3 —CH 2 — Br
2 2
Product (C) is :
OEt
OEt
H
OH
(a)
OH
(b)
OH
OH
OEt
H
OH
(c)
210.
(d) Both (a) and (b)
OH
The following reaction take place in high yields.
CO2CH3
Hg(OAc)
2
¾ ¾¾¾
¾
® Product
D
Use your knowledge of alkene chemistry to predict a product even though you have never
seen this reaction before
CO2CH3
H
(a)
CO2CH3
(b)
HgOAc
HgOAc
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238
CO2CH3
CO2CH3
(c)
(d)
OH
OH
O
211.
O
||
(1 ) O 3
O
||
||
O
O
||
||
O
||
¾ ¾¾
¾® H — C — C — H+ CH 3 — C — C — CH 3 + CH 3 — C — C — H
( 2)Zn
Glyoxal
2, 3- Butanedione
Pyrualdehyde
What is the ratio of glyoxal to pyrualdehyde obtained in the above reaction ?
(a) 1 : 3
(b) 3 : 1
(c) 3 : 2
(d) 2 : 3
CH3
O3
Na
liq. NH 3
212.
¾ ¾¾¾® ( A) ¾ ¾
¾® Products
Zn
Which of the following product cannot be obtained in above reaction ?
O
O
O
O
||
||
||
||
(a) H — C — CH 2 — C — H
O
(b) CH 3 — C — CH 2 — C — H
(c) CH 3 — CH — C — H
(d) None of these
||
|
CHO
213.
CH3
CH3
C == C
CH3
+
–
OsO 4 (10-4 mole)
+ (CH 3 ) 3 N — O + H 2 O ¾¾¾¾¾¾® A + (CH 3 ) 3 N
TMAO
(0.034 moles)
CH3
2, 3-dimethyl-2-butane
(0.025 mole)
(TMAO ® trimethyl amine -N - oxide)
Product (A) is :
(a)
CH3
C—C
CH3
O
CH3
CH3
CH 3
|
(b) CH 3 — C —
|
OH
O
O
||
(c) CH 3 — C — CH 3
CH 3
|
C — CH 3
|
OH
||
(d) CH 3 — C — C(CH 3 ) 3
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239
214.
HO
H3O+
A
Product (A) of the reaction is :
OH
OH
(a)
(b)
(c)
(d) None of these
OH
H+
D
215.
¾¾
¾® ( A)
(major)
Product (A) is :
(a)
(b)
(c)
(d)
CH3
216.
CH3
C == CH2
(a)
CH3
CH3O
C == CH2
(b)
CH3
CH3OCH2
C == CH2
(c)
Arrange the above in the decreasing order of reactivity towards HBr :
(a) a > b > c
(b) b > a > c
(c) b > c > a
(d) a > c > b
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240
217.
+
Which reaction has the lowest DG + or (Activation-Energy)?
HBr
HBr
(a)
(b)
Br
Br
HBr
HBr
(c)
218.
(d)
Br
Br
Which of the following will rearrange ?
+
(1)
(2)
+
(b) 1 and 3
(4)
(c) All
(d) 1, 2, 4,
Which of the following is most likely to undergo a favorable hydride shift ?
(a)
220.
(3)
+
(a) 1
219.
+
(b)
(c)
(d)
Energy profile diagram for dehydration of 2-butanol using conc. H 2 SO 4 is given below :
PE
a
b
c
Å
OH Me – CH – CH
2
|
|
CH3
Me – CH2 – CH – Me
Reaction co-ordinate
Product (b) of above reaction is :
(a) 1-butene
(b) cis-2-butene
(c) trans-2-butene
(d) iso-butene
221.
How many alkene on catalytic hydrogenation given isopentane as a product ?
(a) 2
(b) 3
(c) 4
(d) 5
222.
Which of the following would not rearrange to a more stable form ?
+
+
(a)
+
(b) H
(c)
+
(d)
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241
223.
Consider the following reaction.
SO 2
BrCH 2 CH 2 F + SbF5 ¾ ¾
¾® CH2 —– CH2 + SbF6
- 60°C
+
Br
In this reaction SbF5 acts as:
(a) an acid
(b) a base
(c) a nucleophile
(d) an electrophile
Br hv
Alcoholic
- Br
¾ ¾2 ¾
¾® Major (X) ¾ ¾ ¾ ¾
¾® Major(Y) ¾ ¾H¾
¾® Major(Z):
224.
Peroxide
KOH D
Product ( Z ) is:
Br
Br
(a)
Br
(b)
(c)
(d)
Br
225.
CH3—C ºº C—H
CH3—I
NaNH2
Relation between (B) and (C) is:
(a) Enantiomer
(c) Geometrical isomer
226.
H3
iq N
Li/l
H2
(A)
Pd-CaCO3
(B)
(C)
(b) Diastereomer
(d) Meso
The reaction of HBr with the following compound would produce :
OH
Br
OH
(a)
OH
(b)
Br
Br
Br
(c)
(d)
Br
Br
Br
Br
227.
is an example of:
+ Br2
(a) Nucleophilic addition
(c) Electrophilic addition
(e) Free radical substitution
228.
Olefins can be hydrogenated by :
(a) Zinc and HCl
(c) Raney Ni and H
(b) Nucleophilic substitution
(d) Electrophilic substitution
(b) Nascent hydrogen
(d) Lithium hydride in ether
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242
CH3
229.
What are the products obtained on hydroboration-oxidation of the given alkene
CH3
(I)
CH3
(III)
(II)
H
OH
OH
CH3
(IV)
H
H
OH
H
OH
CH3
(V)
(VI)
H
HO
OH
H
(a) I and III
(b) II and IV
HBr
(c) II and VI
(d) III and V
Hg(OAc)2
(A)
CCl4
230.
CH3
CH3
NaBH4
CH3CH2CººCH
CH3CH2CH == CH2
HBr
R2O2
(B)
B2H6
H2O2/OH
(C)
(D)
Relation between A and B, C and D are :
(a) Position, chain
(b) Chain, Identical
(b) Position, Functional
(d) Metamer, Functional
231. In which reaction syn addition doesn’t take place.
dil.KMnO4
(a)
(b)
(1) B2H6
(c)
(2) H2O2/NaOH
(d)
Ni
D2
Br2
CCl4
HBr
232. Number of olefin of C 4 H 8 ¾® Number of Markonikow product (including stereo)
(y)
( x)
x + y is :
(a) 5
(b) 6
(c) 7
(d) 8
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243
ANSWERS — LEVEL 1
1.
(c)
2.
(d)
3.
(c)
4.
(d)
5.
(b)
6.
(b)
7.
(c)
8.
(c)
9.
(c)
10.
(d)
11.
(b)
12.
(d)
13.
(c)
14.
(b)
15.
(b)
16.
(c)
17.
(d)
18.
(d)
19.
(b)
20.
(d)
21.
(b)
22.
(a)
23.
(b)
24.
(b)
25.
(b)
26.
(b)
27.
(d)
28.
(b)
29.
(d)
30.
(b)
31.
(c)
32.
(b)
(b)
33.
(a)
34.
(b)
35.
(b)
36.
(b)
37.
(b)
38.
(b)
39.
(b)
40.
41.
(d)
42.
(e)
43.
(c)
44.
(c)
45.
(a)
46.
(c)
47.
(c)
48.
(b)
49.
(b)
50.
(b)
51.
(b)
52.
(a)
53.
(b)
54.
(d)
55.
(b)
56.
(c)
57.
(c)
58.
(b)
59.
(c)
60.
(a)
61.
(b)
62.
(d)
63.
(a)
64.
(b)
65.
(d)
66.
(b)
67.
(d)
68.
(a)
69.
(c)
70.
(d)
71.
(d)
72.
(c)
73.
(d)
74.
(c)
75.
(a)
76.
(c)
77.
(d)
78.
(b)
79.
(d)
80.
(d)
81.
(c)
82.
(b)
83.
(a)
84.
(a)
85.
(a)
86.
(d)
87.
(b)
88.
(b)
89.
(c)
90.
(d)
91.
(b)
92.
(b)
93.
(a)
94.
(a)
95.
(a)
96.
(d)
97.
(b)
98.
(a)
99.
(c)
100. (d)
101. (b)
102. (b)
103. (d)
104. (b)
105. (b)
106.
(c)
107. (b)
108. (b)
109. (d)
110. (d)
111.
(c)
112. (b)
113.
114. (b)
115.
(c)
116.
(a)
117. (b)
118. (b)
119. (b)
120. (d)
121. (b)
122.
(c)
123.
(a)
124. (b)
125. (d)
126.
(a)
127. (b)
128.
(c)
129. (d)
130.
(a)
131.
(c)
132. (d)
133.
134.
(a)
135. (d)
136.
(c)
137. (b)
138. (d)
139. (d)
140. (b)
141. (b)
142. (b)
143. (b)
144. (b)
145. (b)
146.
(c)
147. (b)
148.
(a)
149. (d)
150. (b)
151.
152. (d)
153.
(c)
154.
(c)
155. (b)
156.
(c)
157.
158.
(a)
159. (b)
160.
(c)
161. (b)
162.
(c)
163
(b)
164. (d)
165. (d)
166. (b)
167. (b)
168.
(a)
169.
170. (b)
171. (b)
172. (d)
173. (b)
174.
175. (b)
176. (b)
177. (b)
178.
179. (b)
180.
(c)
181. (b)
182. (b)
183.
(c)
184.
185.
(c)
186. (b)
187.
(a)
188. (b)
189. (b)
190. (b)
191.
(a)
192. (b)
193.
(c)
194. (b)
195.
(c)
196.
(c)
197. (b)
198.
(a)
199. (b)
200.
(c)
202.
203. (b)
204. (d)
205. (b)
206.
(c)
207. (b)
208. (b)
201.
(a)
(c)
(c)
(c)
(c)
(a)
(c)
(a)
(c)
(c)
209. (b)
210. (b)
211.
(c)
212.
(c)
213. (b)
214.
(a)
215. (b)
216. (b)
217. (d)
218.
(c)
219.
(a)
220. (b)
221. (b)
222.
(c)
223. (d)
224.
(c)
225. (b,c) 226. (b)
227.
(c)
228.
229. (d)
230. (b)
231
232.
(c)
(c)
(d)
* For question 56 and 57, option (a) is also correct.
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Level - 2
1.
Reagents
A. HCl
B. Br 2
C. Hg(OAc) 2 in H 2 O
D. B 2 H 6(BH 3 ) in ether
E. H 2 O 2
F. KMnO 4 in H 2 O
G. HOBr
H. NaBH 4
In each reagent box write a letter designating the best reagent and condition selected from
the above list of reagents.
Reactant
Reagent
(CH 3 ) 2 CHCH == CH 2
3- methyl-1- butene
2.
Product
(i)
(CH 3 ) 2 CHCH(Cl)CH 3
(ii)
(CH 3 ) 2 CHCHBrCH 2 Br
(iii)
(CH 3 ) 2 CHCHOHCH 2 Br
(iv)
(CH 3 ) 2 CHCH(OH)CH 3
(v)
(CH 3 ) 2 CHCH(OH)CH 2 OH
2-Chloro- 3- methyl butane
1, 2- dibromo- 3- methyl butane
1, bromo- 3- methyl 2- butanol
3- methyl- 2- butanol
3- methyl- 1, 2- butanediol
Propene (CH 3 — CH == CH 2 ) can be transformed to compounds (a to j) listed in the
left-hand column.
Write letter designating the reagent, you believe will achieve desired transformation. In the
case of a multi step sequence write the reagent in the order they are to be used.
Desired Product
No. of Write
Steps options
Reagent List
a.
CH 3 CHBrCH 2 Br
one
A.
Hg(OAc) 2 in H 2 O
b.
(CH 3 ) 2 CHOH
two
B.
B 2 H 6 in THF
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two
C.
NaBH 4 in alcohol
CH 3 COCH 3
three
D.
Br 2 in CH 2 Cl 2
e.
CH 3 CH 2 CHO
three
E.
H 2 O 2 in aqueous base
f.
CH 3 CH(OH)CH 2 Br
one
F.
HOBr (NBS in aqueous acetone)
g.
(CH 3 ) 2 CHBr
one
G.
HBr in CH 2 Cl 2
two
H.
OsO 4 in ether
three
I.
Thionyl chloride (SOCl 2 )
two
J.
NaHSO 3 in aqueous acetone
K.
NaOH in alcohol and reflux
L.
NaNH 2 (strong base)
c.
CH 3 CH 2 CH 2 OH
d.
h, k. CH 3 CH(OH) CH 2 OH
i.
CH 3 - CH 2 - CH 2 - Cl
j.
CH 3 - C º CH
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3.
In each reaction box write a single letter designating the best reagent and condition selected
from the list at bottom of the page.
(F.S., ® first step, S.S ® second step, T.S. ® third step)
Reaction
Reactant
CH3
1.
Options
Product
OH
CH3
F.S.
S.S.
OCH3
CH3
2.
CH3
F.S.
S.S.
T.S.
CH3
3.
O
OH
OH
F.S.
S.S.
O
4.
Ph
F.S.
S.S.
Ph
F.S.
5.
S.S.
T.S.
O
A. NaBH 4 /alcohol
B. Ph - CO 3 H/
CH 2 Cl 2
C. PCC
D.
CH 3 OH
CH 3 ONa/
E. B 2 H 6 in THF
F. H 2 O 2 /aq. NaOH
G. H 3 PO 4 & heat
H. AlCl 3 /C 6 H 6
I. O 3 in CH 2 Cl 2
J. Br 2 in CH 2 Cl 2
K. 20% KOH & heat
L. Ph - Li/ether
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4.
Match the reagents a-j with products A-J. There is one best product for each reaction.
Br
(x)
The molecule (x) is the starting material for all reactions in problem. Do the ones you know
first and then tackle the rest by deductive reasoning
Products
Reagents
Br
Option
H 2 O heat, pH 7
(a)
HO
O
HO
A
(b)
B
F3 C
OH
OH
(c)
C
Br
O
E
Br
Br
O
OH
tBuOK, polar aprotic solvent
(d)
(1) O 3 , ether
(2) H 2 O, NaOH, H 2 O 2
(e)
Br 2 ,CCl 4
(f)
NBS, hv, CCl 4
(g)
(1) H 3 O( +)
(2) NaOH, H 2 O
(h)
(1) BH 3 , ether
(2) H 2 O 2
(i)
(1) OsO 4
(2) NaOH,H 2 O
(j)
H 2 Pd C(EtOH)
O
D
O
HO
F
G
Br
Br
Br Br
OH
H
Br
I
Br
Br
Br
J
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5.
Match the column:
Column (I)
Column (II)
(a) CH 3 ¾ C ºº C ¾ CH 3
(p)
cis-product with H 2 / Pd - BaSO 4
(b) CH 3 ¾ CH 2 ¾ C ºº CH
(q)
Trans-product with Na /liq. NH 3
(c)
(r)
White with amm. AgNO 3
(s)
H 2 gas with Na
CH 3 ¾ C ºº CH
(d) CH 3 ¾ C ººC ¾ Et
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6.
Match the column I with column II and with column III (Matrix).
Column-I
Reaction
(a)
Br
CH3
2
¾
¾
®
H ¾CCl
Column- II
Column- IIII
Nature of product formed
Number of chiral center
present
in
product.
(Consider only one isomer in
case of racemic mixture or
Diastereomer)
(p)
Racemic mixture
(w)
0
(q)
Meso
(x)
1
(r)
Diastereomer
(y)
2
(s)
Vicinal dihalide
(z)
3
4
Br
2
¾¾
¾
®
(b)
H
CCl 4
CH3
Br
2
¾¾
¾
®
CCl 4
(c)
CH3
CH 3
(d)
H
H
C == C
CH 3
Br2
CCl4
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7.
Match the column I and II.
Column (I)
Column (II)
Reaction
Product
OH
(1)OsO
(a)
4
¾ ¾ ¾¾
®
(b)
(1) BH 3 ether
(2) NaOH, H 2O
(p)
Cl
¾¾¾¾¾
¾®
(2) H 2O 2, NaOH, H 2O
(q)
OH
OH
Cl H O
(c)
2
¾ ¾2,¾¾
®
(r)
OH
Cl
(d)
Cl 2 CCl 4
¾ ¾ ¾¾®
(s)
Cl
CH2 — OH
HO
8.
H+
(1)
¾¾
¾® ( A)
D
H+
OH
¾¾
¾® ( B )
D
OH
¾¾
¾® (C )
OH
H+
(2)
OH
(3)
OH
D
(4)
H+
¾¾
¾® ( D)
D
Sum of molecular mass of A, B, C, D (i.e. A + B + C + D) is equal to :
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9.
(1) C 2 FClBrI ¾ H
¾2 ®( A) (exclude stereoisomer)
Ni
(all isomers)
(2) C 4 H 8 (alkene) ¾ H
¾2 ®( B ) (exclude stereoisomer)
Ni
(all isomers)
Total number of products A and B (i.e. A + B) is equal to :
10.
Reaction 1
CH3
H
Reaction 2
CH3
Br
H
CH
Br
CH
2
(cis) ¾ Br
¾
¾
® (P)
2
(trans) ¾ Br
¾
¾
® (Q)
CCl 4
CH
CCl 4
CH
H
Br
H
CH3
CH3
Reaction 3
CH3
H
Reaction 4
CH3
Br
H
CH
2
(cis) ¾ Br
¾
¾
® (R)
CH
Br
Br
CH
2
(trans) ¾ Br
¾
¾
® (S)
CCl 4
CH
CH3
CCl 4
CH3
Sum of products P, Q, R, S (i.e. P + Q + R + S) is equal to :
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11. Comprehension
Vladimir Markovnikov rule :
Alkenes undergo electrophilic addition reactions. It is triggered by the acid acting as
a electrophile toward p-electrons of the double bond.
Markovnikov’s rule states that when an unsymmetrically substituted alkene reacts
with a hydrogen halide, the hydrogen atom adds to the carbon that has the greater
number of hydrogen, e.g.,
CH3
0°C
CH3 + H – Cl
¾¾
¾®
1-methyl cyclopentene
Cl
1-chloro-1-methyl cyclopentane
Mechanism :
CH3 + H – Cl
Step - 1
Å
CH3
Step- 2
Cl –
(fast)
Å
¾ r.d.s
¾¾®
CH3
Cl Q
CH3
Cl -
¾¾
¾®
Cl
(fast)
A. Which of the following is most reactive toward Markovnikov addition ?
O
O
(a)
(b)
(c)
(d)
B. What is the energy profile for the given reaction ?
(a)
(b)
E
E
Reaction co-ordinate
(c)
Reaction co-ordinate
(d)
E
Reaction co-ordinate
E
Reaction co-ordinate
C. In which of following reactions carbocation rearrangement is possible ?
(a) (CH 3 ) 2 CH — CH == CH 2 ¾ HCl
(b) (CH 3 ) 3 C — CH == CH 2 ¾ HBr
¾
¾®
¾
¾®
0 °C
(c) Ph — CH 2 — CH
== CH 2 ¾ HBr
¾
¾®
CCl 4
0 °C / Cl 4
(d) All of these
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D. Identify the major products r1, r2 and r3 in the given reactions.
CH3
OD
CH3
,
,
OH
CH3
OCH3
CH3
,
,
(b)
Br
r1
HBr
CH3OH
r2
HBr
D2O
r3
OCH3
CH3
OH
CH3
(a)
HBr
H2O
OD
CH3
OH
CH3
CH3
(c)
in all the reactions
(d)
in all the reactions
E. In which of the following reactions, product is racemic mixture ?
(a) CH 3 - CH 2 - CH = CH 2 ¾ HBr
¾
¾®
CCl 4
(c)
CH3
H
C=C
(cis)
CH3
¾ HBr
¾
¾®
CCl 4
H
(b)
CH3
H
C=C
H
CH3
¾ HBr
¾
¾®
CCl 4
(d) All of these
F. In which of the following reactions, diastereomers will be formed ?
CH3
H
D
CH
||
CH
CH3
¾ HBr
¾
¾®
(a)
CH3
CCl 4
(b)
¾ HBr
¾
¾®
CCl 4
Br
(c)
¾ HBr
¾
¾®
CCl 4
(d) All of these
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12. Comprehension
HÅ
CH 3 — CH 2 — CH == CH 2 + CH 3OH ¾¾¾® CH 3 — CH 2 — CH — CH 3
|
OCH 3
Consider the above reaction and answer A to E.
A.
What is electrophile in first step ?
Å
(b) H Å
(a) CH 3
Å
B.
C.
(c) CH 3 — CH 2 — CH — CH 3
(d) HO Å
What is nucleophile in first step ?
(a) CH 3OH
(c) H 2O
(b) 1-butene
(d) CH 3 - O - CH 3
What is electrophile in second step ?
Å
(b) H Å
(a) CH 3
Å
D.
E.
Å
(c) CH 3 — CH 2 — CH — CH 3
(d) CH 3 — CH 2 — CH 2 — CH 2
What is nucleophile in second step ?
(a) CH 3 — CH 2 — CH == CH 2
(c) H 2O
(b) CH 3OH
(d) CH 3 — O — CH 3
Which step is rate determining step ?
(a) attack of nucleophile CH 3OH
(b) attack of electrophile H Å
(c) attack of nucleophile H 2O
(d) attack of electrophile CH 3
Å
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13. Match the column I and II :
Column (I)
Column (II)
Conversion
Reagent
CH3
(a)
¾®
Br
Br
(p)
SO2Cl2 / hv (2 equivalent)
(q)
NBS (2 equivalent)
(r)
NBS then SO2Cl2/hv
CH2 – Cl
CH3
(b)
¾®
CH3
Cl
Br
(c)
¾®
Cl
CH2 –Cl
CH3
(d)
¾®
Br
(s)
SO2 Cl2 / hv then NBS
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ANSWERS — LEVEL 2
1.
(i) – A; (ii) – B; (iii) – G; (iv) – C; (v) – F
2.
a – D; b – A, C; c – B, E; d – A, C, F; e – B, E, F; f – F; g – G; h – I, K; i – B, E, I; j – D, L
3.
Reaction 1 : B, D;
Reaction 2 : E, F, C
Reaction 4 : L, G
Reaction 5 : B, L, C
Reaction 3 : I, A
4.
a – C; b – D; c – A; d – F; e – I; f – J; g – E; h – H; i – B; j – G
5.
a – p, q; b – r, s; c – r, s; d – p, q
6.
a – r, s – z; b – p, s – y; c – p, s – y; d – q, s – y
7.
a – r; b – p; c – q; d – s
8.
A + B + C + D = 312
9.
A + B =5
10.
P + Q + R + S =8
11.
A – b; B – c; C – d; D – b; E – d; F – d
12.
A – b; B – b; C – c; D – b; E – b
13.
a-q; b-p; c-s; d-r
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4C
HYDROCARBONS (ALKYNES)
Level - 1
O
||
C — CH3
(1) 3NaNH 2 ,
PCl
mineral oil
5
¾ ¾¾
® ( A) ¾ ¾¾¾¾
® ( B ) ; Product (B) is :
Å
1.
0 °C
(2) H
70- 80%
CH == CH2
(a)
CH2
C ºº CH
(b)
(c)
(d)
Br
alc.KOH
2
¾CCl
¾
¾
® ¾(i)
¾¾¾
¾® ( A) ; Product (A) is :
(ii) NaNH
2.
3.
46%
4
2
major
(a) H 2C == CH — CH == CH 2
(b) CH 3 — C ºº C — CH 3
(c) CH 3 — CH 2 — C ºº CH
(d) CH 3 — CH == C == CH 2
NaNH 2
CH 3CH 2C ºº CH ¾ ¾¾
¾® I
liq. NH
Et2O
Product (K) of the above reaction is :
O
Å
H
J ¾¾
¾® ( K )
3
OH
O
C ºº C — Et
C ºº C — Et
(a)
(b)
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OH
OH
(c)
4.
C ºº C — CH3
C ºº C — CH2 — CH3
(d)
(CH ) SO
3 2
4
CH 3 — CH 2 — CH 2 — C ºº CH + LiNH 2 ¾¾® ( A) ¾ ¾¾¾
¾
® ( B)
Lithium
amide
Give the structural formula of compound (B) :
(a) CH 3 — (CH 2 ) 2 — C ºº C — SO 3H
(b) CH 3 — (CH 2 ) 2 — C ºº C — CH 3
O
||
(c) CH 3 — (CH 2 ) 2 — C ºº C — CH 2 — O — S — H
||
O
(d) CH 3 — CH 2 — C ºº C — CH 2
CH2 – CH2 – CH3
5.
; This conversion can be acheived by :
(a) NaNH 2 , CH 3CHO
(c) KOH, CH 3 — CH 2 — Br
6.
Which alkyne will give 3-ethylhexane on catalytic hydrogenation ?
(a)
7.
(b) NaNH 2 , CH 3 — CH 2 — CH 2 — Br
(d) KOH, CH 2 — CH 2
|
|
Br
Br
(b)
(c)
(d) All of these
Reactant P gives products Q or R.
H
H
(CH2)4
(CH2)4
or (H2C)4
H
P
Q
H
R
The possible reagents are :
(I) 2Na liq.NH 3
(II) H 2 Pd CaCO 3 (quinoline)
(III) 2H 2 Pd C
The correct statement with respect to the above conversion is/are :
(a) Q is obtained on treatment with reagent (I)
(b) R and Q are obtained on treatment with reagent (II)
(c) R is obtained on treatment with reagent (I)
(d) R is obtained on treatment with reagent (II)
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8.
NaNH 2
Lindlar
Br — (CH 2 ) 12 — C ºº CH ¾ ¾¾
¾® ( A) ¾Catalyst
¾¾
¾® ( B) ; Product (B) is :
H
(a)
(b)
H
H
(c)
9.
(d) Br — (CH 2 ) — CH == CH 2
MeO –
Ph — C ºº CH ¾ ¾¾
¾® Major product of the reaction is :
MeOH
H
Ph
(a)
10.
(b)
H
H
OMe
Ph
C ==C
C == C
H
H
(c) Ph — C ºº C — OMe
(d) Ph – C == CH2
Cl
OMe
|
3NaNH 2
Ph ¾ C ¾ CH 3 ¾¾¾® ( A) ; Product (A) is :
Product
|
Cl
(a) Ph ¾ CH == CH 2
11.
H
(b) Ph ¾ C ºº CH
sr
(c) Ph ¾ CH 2 ¾ CH 3 (d) Ph ¾ C ººCNa
Which combination is best for preparation of the compound (A) shown below ?
CH3
H
C — CH2CH2CH2C ºº CH
CH3CH2 (A)
CH3
H
(a) H3C
NaC ºº CH
C — CH2CH2CH2Br ¾¾¾®( A) (b)
H
CH3CH2
CH3CH2
CH3
H
(c) H3C
1. NaNH 2 , NH 3
C — Br ¾¾¾¾¾¾¾¾® ( A) (d)
CH3CH2
12.
NaC ºº CH
C — CH2CH2CH2Br ¾¾¾®( A)
H
1. NaNH 2 , NH 3
C — Br ¾¾¾¾¾¾¾¾® ( A)
2. BrCH 2CH 2CH 2C ºº CH
2. BrCH 2CH 2CH 2C ºº CH
CH3CH2
Which one of the following is the intermediate in the preparation of a ketone by hydration of
an alkyne in the presence of sulfuric acid and mercury (II) sulphate ?
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OH
(a) HO
(b)
(c)
OH
A
13.
B
¾® ¾®
O
14.
(d)
OH
O
O — CH2 — C ºº CH
O — CH2 — C ºº C — CH2 — CH2 — CH2 — Br
To carry out above conversion, (A) and (B) respectively, are :
(a) NaNH 2 ,Cl — CH 2 — CH 2 — CH 2 — Br
(b) NaNH 2 , F — CH 2 — CH 2 — CH 2 — Br
(c) NaNH 2 , I — CH 2 — CH 2 — CH 2 — Br
(d) NaNH 2 , I — CH 2 — CH 2 — CH 2 — I
I2
H — C ºº C — Ph
Product; Product obtained in this reaction is :
O
H–N
(a) Ph — C == CH — I
|
I
(c) Ph — C ºº C — I
(b) Ph — C H — CH 2 — I
|
I
(d) I — C ºº C — H
H
(i) NaNH , NH
2
2
3
C ºº CH ¾ ¾¾¾¾¾
® (A) ¾ ¾¾¾¾
¾® (B) ; Product ( B ) is :
Lindlar catalyst
15.
(ii)CH 3 Br
H
C ºº
H
C — 3 CH
CH3
C
C == C
(a)
16.
17.
(b)
H
C
(c)
C
C
H
H
H
H (d)
CH3
Which of the following alkyne on treatment with H 2 (2 mole)/ Pt gives an optically inactive
compound ?
(a) 3-Methyl-1-pentyne
(b) 4-Methyl-1-hexyne
(c) 3-Methyl-1-heptyne
(d) None of the above
H 2O
Red hot Cu tube
¾ ¾¾® ( A) ¾ ¾¾¾¾¾® ( B ) , Product (B) of the reaction is :
CaC 2
(Calcium carbide)
18.
(a) Toluene
(b) Ethyl-benzene
(c) Benzene
What is the final product, C, of the following reaction sequence ?
(d) Butyne
1. NaNH 2
H ¾ ¾¾¾¾
¾® A
2. CH CH Br
3
2
Na, NH 3 (liq.)
A ¾ ¾¾¾¾
¾® B
Br
2
B ¾CH
¾¾
¾® C
Cl
2
2
Br
Br
Br
(a)
(b)
Br
Br
(c)
(d)
NH2
Br
Br
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19.
Compound (X)
5H2
CH2 — CH2 — CH2 — CH3
Pt
AgNO3
Precipitate
O O
O
O O
|| ||
||
||
||
CHO
H — C — CH2 — CH2 — C — C — H + H — C — C — O – H + H — C — O – H + |
CHO
O
O3
Me2S
Compound (X) will be :
CH == CH — C ºº CH
(a)
(c)
20.
CH — CH2 — C ºº CH
(b)
CH — CH2 — C ºº CH
(d)
C == CH — C ºº CH
Choose the sequence of steps that describes the best synthesis of 1-butene from ethanol :
(a) (1) NaC ºº CH ; (2) H 2 , Lindlar Pd
(b) (1) NaC ºº CH ; (2) Na, NH 3
(c) (1) HBr, heat ; (2) NaC ºº CH ;
(3) H 2 , Lindlar Pd
(d) (1) HBr, heat ; (2) KOC(CH 3 ) 3 , DMSO ; (3) NaC ºº CH ; (4) H 2 , Lindlar catalyst
21.
Which alkyne yields butanoic acid (CH 3CH 2CH 2CO 2H) as the only organic product on
treatment with ozone followed by the hydrolysis ?
(a) 1-Butyne
(b) 4-Octyne
(c) 1-Pentyne
(d) 2-Hexyne
22.
2
(A) ¾ ¾
¾
®
Pt
2H
CH2 — CH2 — CH2
O
Carlina oxide
Unit of unsaturation in compound (A) ?
(a) 7
(b) 8
(c) 9
(d) 10
O
23.
Å
Kolbe electrolysis
H 3O
NaOH
O ¾ ¾¾
® ( A) ¾ ¾¾
® ( B ) ¾¾¾¾¾¾® (C)
O
Product (C) of above reaction is:
(a) H 2C == CH 2
(c) HC ºº CH
24.
(b) CH 3 — C ºº C — CH 3
(d) CH 3 — CH == CH — CH 3
To convert 1-butyne to 1-D-butanal, one would carry out the following steps :
(I) Sodium amide, then D 2O
(II) Disiamy lborane, then hydrogen peroxide/sodium hydroxide
(III) The transformation can not be carried out with the indicated reagents.
(a) I, followed by II (b) II, followed by I (c) III
(d) II
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25.
An unknown compound ( A) has a molecular formula C 4 H 6 . When (A) is treated with excess
of Br 2 a new substance ( B ) with formula C 4 H 6 Br 4 is formed. (A) forms a white ppt. with
ammonical silver nitrate solution. ( A) may be :
(a) But-1-yne
(b) But-2-yne
(c) But-1-ene
(d) But-2-ene
26.
One mole of 1,2-dibromopropane on treatment with X moles of NaNH 2 followed by
treatment with ethyl bromide gave a pentyne. The value of X is :
(a) One
(b) Two
(c) Three
(d) Four
27.
28.
CH3
|
CH3 – CH – C ºº CH
excess HBr
¾ ¾¾¾
¾®
The product of the above reaction is :
CH3 Br Br
|
|
|
(a) CH3 – CH – CH – CH2
CH3 Br
|
|
(b) CH3 – CH – C = CH2
CH3 Br
|
|
(c) CH3 – CH – C – CH3
|
Br
Br
CH3
|
|
(d) CH3 – CH – CH2 – CH
|
Br
KMnO 4
CH 3 — C ºº C — CH 3 ¾Cold
¾¾¾¾
®( A)
Product (A) is:
O O
(a)
O O
(b)
CH3—CH2—C—C—H
CH3—C—C—CH3
OH OH
(c)
29.
(d) O == CH — CH 2 — CH 2CH == O
CH3—CH—CH—CH3
In which reaction last product is Ph — C ºº CH ?
Br
|
3NaNH 2
NH 4Cl
(a) C 6 H 5 —C — CH 3 ¾ ¾¾¾¾
¾® ¾ ¾¾
¾®
Mineral oil, heat
|
Br
3NaNH 2
Br
NH Cl
2
4
(b) C 6 H 5CH == CH 2 ¾CCl
¾
¾
® ¾ ¾¾¾¾¾
® ¾ ¾¾
¾®
Mineral oil, heat
4
O
||
3NaNH 2
PCl 5
NH 4Cl
(c) C 6 H 5 — C — CH 3 ¾ ¾¾
® ¾ ¾¾¾¾¾
® ¾ ¾¾
¾®
Mineral oil, heat
(d) All
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30.
Predict the product of the following reaction sequence.
(1) excess NaNH
2
ethyne ¾ ¾¾¾¾¾¾¾¾¾¾
¾®
(2) excess I—CH 2 —(CH 2 )2 —CH 3
r
(3) H
(a) 6-iodo-1-hexyne
(c) 5-decyne
31.
(b) 1-hexyne
(d) 1-iodo-1-hexene
The best sequence of reactions to prepare 2-heptanone is
2+
H 2O , Hg
NaNH 2
n-C 4 H 9 Br
(a) propyne ¾ ¾¾
¾® X ¾ ¾¾¾
¾® Y ¾ ¾¾¾
¾®
H SO
2
NaNH 2
n-C 5 H12 Br
(b) ethyne ¾ ¾¾
¾® X ¾ ¾¾¾¾® Y
4
H 2O , Hg 2+
¾ ¾¾¾
¾®
H 2SO 4
2+
H 2O. Hg
NaNH 2
2 Br
(c) 1 - hexyne ¾ ¾¾
¾® X ¾CH
¾¾
® Y ¾ ¾¾¾
¾®
H 2SO 4
2+
H 2O, Hg
(d) 1 - pentyne ¾ ¾¾
¾® X ¾ ¾¾¾® Y ¾ ¾¾¾
¾®
NaNH 2
C 2 H 5 Br
H 2SO 4
32.
The major product of the reaction of 2-butene with cold alkaline KMnO 4 , is
(a)
(b)
O
O
(c)
O
(d)
OH
OH
ANSWERS — LEVEL 1
1.
(b)
2.
(b)
3.
(b)
4.
(b)
5.
(b)
6.
(d)
7.
(c)
8.
(c)
9.
(b)
10.
(d)
11.
(b)
12.
(d)
13.
(c)
14.
(c)
15.
(c)
16.
(a)
17.
(c)
18.
(a)
19.
(a)
20.
(c)
21.
(b)
22.
(c)
23.
(c)
24.
(c)
25.
(a)
26.
(c)
27.
(c)
28.
(b)
29.
(d)
30.
(c)
31.
(b)
32.
(d)
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264
5A
ALKYL HALIDES
Substitution Reactions (SN , SN , SN )
1
2
i
Level - 1
1.
Which of the following is not expected to be intermediate of the following reaction ?
OH
I
H2O
+
+
OH2
+
(a)
(b)
(c)
(d)
+
CH3
2.
Br
H
H
CH3
+ NaI ¾ ¾¾¾® product; S N 2 product of the reaction is :
Acetone
CH2 – CH3
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CH3
CH3
I
(a)
H
H
CH3
(b)
H
I
H
CH3
CH3
CH3
CH3
(d)
I
H
CH3
H
CH2 – CH3
CH2 – CH3
Rate of S N 2 will be negligible in :
Br
Br
(a)
4.
I
(c)
H
CH2 – CH3
CH2 – CH3
3.
CH3
Br
(b)
Br
(c)
(d)
What is the major product obtained in the following reaction ?
CH2–Br
NH 3
¾ ¾¾® product
Br
CH2–NH2
(a)
EtOH
CH2–Br
(b)
Br
CH2–NH2
CH2–NH2
(c)
(d)
NH2
NH2
CH 3
|
5.
Cl - CH 2 - C - CH 2 - CH 2 – Cl + I - ¾ ¾¾® product; Major product of this reaction is:
DMF
|
CH 3
CH 3
CH 3
|
|
(a) I - CH 2 - C - CH 2 - CH 2 – Cl
(b) Cl - CH 2 - C - CH 2 - CH 2 - I
|
|
CH 3
CH 3
CH 3
CH 3
|
|
(c) H 2 C = C - CH 2 - CH 2 = Cl
(d) Cl - CH 2 - C - CH 2 = CH 2
|
CH 3
6.
Which of the following expressions is representative of the rate law for a S N 2 reaction ?
(a) Rate = k [electrophile]
(b) Rate = k [electrophile] [nucleophile]
(c) Rate = k [nucleophile] 2
(d) Rate = k[electrophile]2
7.
H
Br
(a) H
I
F+ NaI (1 mole) ¾ Acetone
¾¾¾® ( A) ; Major product of this reaction is :
(major)
H
F
H
(b) I
H
F
H
(c) H
Br
I
H
(d) H
Br
H
I
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8.
Which of the following alkyl halide undergo rearrangement in S N1 reaction ?
CH 3
Cl
I
|
(c)
(d) All of these
(a) CH 3 – C – CH – CH 3 (b)
|
|
CH3
CH 3 I
9.
Arrange the following three chlorides in decreasing order towards S N1 reactivity.
Cl
(1)
(2)
(3)
Cl
(a) 1 > 2 > 3
(c) 2 > 1 > 3
10.
Which compound undergoes nucleophilic substitution with NaCN at the fastest rate ?
(a) Br
11.
(b)
Br
(1)
13.
(c) Br
(d) Br
Rank the following in order of decreasing rate of solvolysis with aqueous ethanol (fastest ®
slowest)
CH3
CH 3
Br
|
|
Br
CH 3 - CH CH 2 CH(CH 3 ) 2
H 2 C = C — Br
(2)
(a) 2 > 1 > 3
(c) 2 > 3 > 1
12.
Cl
(b) 2 > 3 > 1
(d) 3 > 2 > 1
(3)
(b) 1 > 2 > 3
(4) 1 > 3 > 2
The reaction of 4-bromobenzyl chloride with sodium cyanide in ethanol leads to the
formation of :
(a) 4-bromobenzyl cyanide
(b) 4-cyanobenzyl chloride
(c) 4-cyanobenzyl cyanide
(d) 4-bromo-2-cyanobenzyl chloride
Which of the following reactant will not favour nucleophilic substitution reaction ?
(a)
(b) Ph - Br
Br
CH 3
|
(c) CH 3 - C - CH 2 - Br
(d) All the above
|
CH 3
Br
OH
OH –
14.
H
(I)
H
(II)
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Conversion of I to II :
(a) takes place by S N1
(c) takes place both by S N1 and S N 2
15.
(b) takes place by S N 2
(d) does not take place
Which is the correct reaction coordinate diagram for the following solvolysis reaction ?
CH3
CH3
H2O
Br
OH
OH
CH3
?
(a)
(b)
Reaction Coordinate
Reaction Coordinate
(c)
(d)
Reaction Coordinate
14C
Reaction Coordinate
labelled
OTs
RCO H
16.
no label
2
¾ ¾¾
¾® product; Product of this reaction is :
OCOR
OCOR
(a)
(b)
(c) both (a) and (b)
(d) None of these
I
CH3
17.
NBS
CH 3SNa
® (B) , Product (B) is :
¾ ¾¾® (A) ¾ ¾¾¾
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268
I
I
CH2–S–CH3
S–CH3
(a)
(b)
S–CH3
CH2–Br
(c)
18.
(d) None of these
Which of the following represents the correct graph for S N 2 reaction ?
log (rate)
(a)
CH3 – Br CH3 – CH2– Br CH3 – CH– Br
CH
|
|
CH3 CH3 – C – Br
|
CH3
log( rate)
(b)
CH3 – Br
Et – Br
i – Pr – Br
t – Bu – Br
log (rate)
(c)
CH3 – Br
Et – Br
i – Pr – Br
t – Bu – Br
(isopropyl)
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log (rate)
(d)
CH3 – Br
19.
Et – Br
i – Pr – Br t – Bu – Br
Which of the following graph represents correct graph for S N1 reaction :
log (rate)
(a)
CH3 – Br CH3 – CH3– Br CH3 – CH– Br
CH3
|
|
CH3
CH3 – C – Br
|
CH3
log (rate)
(b)
CH3 – Br
Et – Br
i – Pr – Br
t – Bu – Br
CH3 – Br
Et – Br
i – Pr – Br
t – Bu – Br
log (rate)
(c)
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log (rate)
(d)
Et – Br
CH3 – Br
20.
i – Pr – Br t – Bu – Br
Which of the following is most reactive toward S N 2 reaction ?
Cl
Cl
(a)
(b)
(c)
CH3
21.
Cl
Cl
(d)
NO2
Cl
Among the given pairs, in which pair first compound reacts faster than second compound in
S N1 reaction ?
(a) CH 3 - CH 2 - CH 2 - CH 2 - Br or CH 3 - CH 2 - CH - CH 3
|
CH 3
CH 3
Br
|
|
(b) CH 3 - C - CH 2 - CH 2 or CH 3 - CH - CH - CH 3
|
|
Br
Br
Br
Br
(c)
or
CH 3
CH 3
|
(d) CH 3 - C - CH 3
|
22.
|
or CH 3 - C - CH 3
|
I
Br
What is the major product of the following reaction ?
HBr
H 2 C = CH - CH 2 - OH ¾excess
¾¾® Product
Br
|
(a) CH 3 - CH - CH 2 - Br
Br
(b) H 2 C = CH - CH 2 - Br
OH
(c) CH 3 - CH - CH 2 - OH
(d) CH 3 - CH - CH 2 - OH
|
|
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23.
S N1 and S N 2 products are same with (excluding stereoisomer) :
Cl
(a)
(b)
Cl
(c)
(d) Ph - CH - CH - CH 3
Cl
24.
|
|
CH 3 Cl
Consider the nucleophilic attacks given below. Select in each pair that shows the greater S N 2
reaction rate.
O
Br + ¯CN
(A)
(I)
or
(III)
Br + I - in DMSO
or
(V)
(VI)
Br + Cl -
Br + I - in methanol
or
(VII)
(VIII)
A
B
C
D
(a) (I) ; (IV) ; (VI) ; (VIII)
(c) (I) ; (III) ; (V) ; (VIII)
25.
H 3 C - Br + CH 3 SH
(IV)
Br + Cl -
(D)
CH3+ ¯CN
(II)
(B) H 3 C - Br + - SH
(C)
O
or
A
B
C
D
(b) (II) ; (III) ; (V) ; (VIII)
(d) (I) ; (III) ; (V) ; (VII)
Which of the two stereoisomers of 4-t-butylcyclohexyl iodide ( 127 I - ) will undergo S N 2
substitution with
128 -
I faster, and why ?
H
H
I127
H
H
I127
(A)
H
(B) H
(a) A will react faster because it is the more stable of the two isomers
(b) A will react faster because it will yield a more stable product, and the transition state for
both reactions is of the same energy
(c) A will react faster because the approach of 128 I - can depart unhindered.
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(d) B will react faster because it is less stable than A, and the transition state for both
reactions is of the same energy
26.
(Z )-2-Butene reacts with Br 2 H 2 O. The resulting bromohydrin when treated with
methoxide in methanol undergoes an intramolecular S N 2 reaction. Taking into
consideration the stereochemical consequences of the reaction mechanism involved,
choose the final product(s) of these transformations.
O
(I)
H
H3C
(II) H3C
H
(a) (I) only
(c) (III) only
27.
(III)
H
CH3
H
H3C
H
CH3
(b) (II) only
(d) Equal amounts of (I) and (II)
Rank the following species in order of decreasing nucleophilicity in a polar protic solvent
(most ® least nucleophilic) :
O
CH 3 CH 2 CH 2 O (1 )
(a) 3 > 1 > 2
28.
O
O
CH3
H
CH 3 CH 2 CH 2 S ( 2)
(b) 2 > 3 > 1
||
CH 3 CH 2 C - O –
( 3)
(c) 1 > 3 > 2
(d) 2 > 1 > 3
Identify products of the given reactions :
OTs
CH CO Na
3
2
¾ ¾¾¾
¾® Product
Reaction-1
NMe2
CH 3CO 2H
OTs
CH CO Na
3
2
¾ ¾¾¾
¾® Product
Reaction-2
NMe2
O
(a)
CH3
CH 3CO 2H
O
;
O
NMe2
O
CH3
O
NMe2
CH3
+ enantiomer
O
CH3
(b)
+ enantiomer ;
O
NMe2
O
CH3
(c)
single product is obtained in both the reactions
O
NMe2
CH3
O
(d)
O
NMe2
O
NMe2
single product obtained in both the reactions
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log(rate)
29.
A
B
CH3–X Me–CH2–X Me2CH–X
Me3CH–X
Which of the following is true about given graphs A and B ?
(b) A ® S N 2 , B ® S N1
(a) A ® S N1 B ® S N 2
(c) A & B ® E 1
(d) A & B ® E 2
30.
In each of the following groups, which is the strongest (best) nucleophile ?
(I) (1) H 3 C - O -
(2)
(II) (1) OH -
(2) H 2 O
(3) H 3 C - S - in CH3OH
O¯
(3) NH -2 in DMF
O¯
(III) (1)
(2)
O¯
(a) I,3 ; II,3 ; III,2
(c) I,1; II,2 ; III,1
(3) CH 3 O - in DMSO
(b) I,2 ; II,1 ; III,3
(d) I,3 ; II,1 ; III,3
O
NaNH
2
¾¾¾¾¾
¾® ( A) ; Product ( A) is :
S – (CH2)4 – CH2 – Cl ¾ dimethoxy
ethane
31.
(Major)
O
O
O
||
(a)
S - (CH 2 ) 3 - CH = CH 2
||
(b)
S
O
O
O
||
(c)
S - (CH 2 ) 4 - CH 2 - NH 2
||
(d) None of these
O
32.
Which of the following reaction is an elimination reaction ?
H
H
(a)
H2SO4
OH ¾¾¾®
Br
+H
(b)
H
KI
¾¾®
+ IBr + KBr
Br
H
H
(c)
Br
NaOCH3
¾¾¾®
OCH3
(d) both (a) and (b)
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CH 3ONa
33.
¾ ¾¾¾¾
¾® Product
CH 3OH(S
CH2 – Cl
O
N1
)
Which of the following products can be obtained from above reaction ?
(a)
34.
(b)
CH2 – OCH3
O
O
CH3O
OCH3
(c)
(d) All of these
CH3
O
What is the principal product of the following reaction ?
CH3
H
Br
H
H
H
Cl
+ NaN 3 ¾® Product
CH3
CH3
N3
H
N3
H
N3
H
H
N3
(a) H
H
(b) H
H
(c) H
H
(d) H
H
H
Cl
Cl
H
H
Cl
Cl
H
CH3
CH3
35.
CH3
CH3
CH3
CH3
CH3
What would be the effect of increasing solvent polarity on the rate of each of the following
reactions ? (Nu = neutral nucleophile)
Å
(A) Nu + R - L ¾® Nu - R + L-
36.
(a) increases
(b) decreases
(B) R - LÅ ¾® R Å + : L
(c) constant
(d) can not be predicted
(a) increases
(c) constant
(d) cannot predict
(b) decreases
Which of the following is most reactive toward S N 2 reaction ?
(a) CH 2 = CH - CH 2 - Cl
(b) Ph - CH 2 - Cl
(c) Me – O
(d) Ph - C - CH 2 - Cl
Cl
||
O
37.
4-chloro-1-butanol + NaOH ¾® ( B )
Product ( B ) of the above reaction is :
CH3
(a)
O
(b)
O
(c) O
CH2 – CH3
(d)
O
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38.
In the given pairs of alkyl-halide, in which pair the first compound is more reactive than
second compound toward S N 2 reaction ?
(a) (CH 3 ) 2 CHBr or CH 3 - CH 2 - CH 2 - Br
(b) CH 3 - CH 2 - CH 2 - Br or CH 3 - CH 2 - CH 2 - I
(c) Ph - Br or CH 3 - CH 2 - CH 2 - Br
(d) CH 2 = CH - CH 2 - Cl or H 2 C = CH - Cl
39.
In the given pair of reaction in which pair the second reaction is more reactive than first
toward S N 2 reaction ?
(a) CH 3 - CH 2 - Cl + CH 3 - CH 2 - O – ¾® Et - O - Et
(or)
CH 2 - CH 2 - Cl + CH 3 - CH 2 - OH ¾® Et - O - Et
(b) CH 3 - CH 2 - Cl + EtO - ¾® Et - O - Et
(or)
CH 3 - CH 2 - Cl + EtS – ¾® CH 3 - CH 2 - S - Et
(c) Et - Cl + CH 3 O - ¾® Et - O - CH 3
(1m)
Et - Cl +
(2m)
( 2m)
CH 3 O (1m)
(or)
¾® Et - O - CH 3
Å
(d) Et - Br + Ph 3 P ¾® Et - PPh 3
(or)
Å
Et - Br + Ph 3 N ¾® E + - NPh 3
40.
Among the following pair of reactions in which pair the second reaction is more reactive than
first in S N1 reaction ?
(a) Me 3 CCl + H 2 O ¾® Me 3 COH
(or)
Me 3 CBr + H 2 O ¾® Me 3 COH
(b) Me 3 CCl + CH 3 OH ¾® Me 3 C — OCH 3 (or) Me3C—Cl + H2O
Me3C—OH
(c) Me 3 CCl + H 2 O ¾® (or) Me 3 CCl + H 2 O
(1M)
(2M)
(d) All of these
41.
Which is a true statement concerning the transition state of an S N 2 reaction ?
(a) Closely resembles a carbocation intermediate
(b) The electrophile is responsible for the reaction
(c) Lower is energy than the starting materials
(d) Involves both the nucleophile and electrophile
42.
Increasing the concentration of a nucleophile in a typical S N 2 reaction by a factor of 10 will
cause the reaction rate to :
(a) increase by a factor of 10
(b) increase by a factor of 10 2
(c) decrease by a factor of 10
(d) remain about the same
43.
Decreasing the concentration of an electrophile in a typical S N 2 reaction by a factor of 3 will
cause the reaction ratio to :
(a) increase by a factor of 3
(b) increase by a factor of 3 2
(c) decrease by a factor of 3
(d) remain about the same
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276
44.
Increasing the concentration of an electrophile in a typical S N 2 reaction by a factor of 3 and
the concentration of the nucleophile by a factor of 3 will change the reaction rate to :
(a) increase by a factor of 6
(b) increase by a factor of 9
(c) decrease by a factor of 3
(d) remain about the same
45.
Consider the following reaction and select the best choice that represents the reaction.
CH3
H
Br
Na Å - SCH CH
2
3
¾ ¾¾¾¾¾
¾
® Product
CH3
CH3 CH3
H
SCH2CH3
(a)
H
SCH2CH3
(b)
CH3 CH3
CH3
(c)
H
SCH2CH3
(d)
H
S – CH2CH3
I
Me
46.
H
KSH
D ¾ ¾¾® Product; Identify the product.
Et
H
SH
Me
(a)
H
H
D
Et
(b)
H
D
Et
HS
(c)
Me
D
(d) Et
H
H
The reaction ,
H
H
OH
Cl
+ SO2 + HCl
+ SOCl2
proceeds by the........... mechanism.
(a) S N i
(b) S N 2
48.
H
Me
D
Et
SH
H
47.
SH
H
Me
(c) S E 2
(d) S N1
Consider the following anions.
O
O
–
CF3 – S – O
O
(I )
C6H5 – S – O
–
O
–
O
CH3 – C – O–
O
( II )
(III)
( IV )
When attached to sp 3 -hybridized carbon, their leaving group ability in nucleophilic
substitution reaction decreases in the order :
(a) I > II > III > IV (b) I > II > IV > III (c) IV > I > II > III (d) IV > III > II > I
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Ph
CH3
H
49.
sr
Ph S N a
¾ ¾¾¾® Principal organic product of the reaction will be :
H
Cl
S
N2
Ph
Ph
Ph
CH3
H
(a) PhS
H
Ph
Ph
CH3
Ph
Cl
H
SPh
Ph
Ph
(c)
CH3
H
(b) H
CH3
H
(d) H
Ph
Ph
Ph
50.
Reaction of R-2-butanol with p-toluenesulphonyl chloride in pyridine followed by reaction
with LiBr gives:
(a) R-2-butyl bromide
(b) S-2-butyl tosylate
(c) R-2-butyl tosylate
(d) S-2-butyl bromide
51.
The compound which undergoes S N1 reaction most rapidly is :
(a)
Br
(b)
Br
(c)
CH2Br
(d)
Br
52.
Addition of KI accelerates the hydrolysis of primary alkyl halides because :
(a) KI is soluble in organic solvents
(b) the iodide ion is a weak base and a poor leaving group
(c) the iodide ion is a strong base
(d) the iodide ion is a powerful nucleophile as well as a good leaving group
53.
Which of the following phrases are not correctly associated with S N1 reaction ?
(1) Rearrangement is possible
(2) Rate is affected by polarity of solvent
(3) The strength of the nucleophile is important in determining rate
(4) The reactivity series is tertiary > secondary > primary
(5) Proceeds with complete inversion of configuration
(a) 3, 5
(b) 5 only
(c) 2, 3, 5
(d) 3 only
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CH3
SO Cl
hv
NBS
KSH
2 2
¾ ¾¾
¾® (A) ¾ ¾¾® (B) ¾ ¾¾® (C) , Product (C) is :
54.
SH
(a)
55.
Br
Cl
(b)
Br
Br
SH
SH
(c)
1
(d)
2
3
Energy profile diagram for an exothermic reaction, A ¾® B ¾® C ¾® D, is given below.
1
2
B
P.E.
A
3
C
D
Progress of the reaction
The rate determining step of the reaction is :
(a) A ¾® B
(b) B ¾® C
(c) C ¾® D
(d) can not predict
CH3
NBS
56.
¾¾® ( A)
Major
Major product (A) is :
Br
Br
(a)
(b)
(c)
(d)
Br
Br
57.
Cl
LiBr /DMSO
¾ ¾¾¾¾® Major product (X)
Cl
S
N2
conditions
The product X is :
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Br
(a)
Cl
(b)
Cl
Br
(c)
58.
Br
Cl
(d)
Br
Relative rate of reaction of the following amine with methyl iodide is:
N
N
(A)
(a) A > B > C
N
N
(B)
(C)
(b) A > C > B
(c) B > C > A
(d) B > A > C
H
PhCH2O
59.
H
OTs
H
C
C
H
NaI
Dimethyl sulfoxide
OCH3
C
¾ ¾¾¾¾¾¾
¾®
OCH3
Major product which you expect in the above reaction is :
H
H
OTs
I
I
OCH2Ph C
C
H
H
C
C
OCH3
C
(a)
(b)
OCH3
C
H
H
H
H
OCH3
OCH3
I
OCH2Ph C
C
(c)
H
HS
H
H
H
C
OCH3
(d)
aqueous EtOH
(A)
I
C
H
OCH3
+
(major)
C6H10S
Cl
H
Major product of the above reaction is :
HS
(b)
H
H
OTs
HS
NaOH in
(a)
H
OCH3
H
60.
H
OCH2Ph
C
C
S
H
SH
(c)
S
(d)
OH
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H
61.
CH3 — C — C14 — CH3 ¾¾® Major product of the reaction is:
D
CH3 OTs
(a)
CH3
14
C
(c)
CH3
C
CH3
62.
14
(b) CH3 — C — CH
C
CH3
CH3
Ph
Ph
14
CH2
CH3
CH3
Ph
(d)
C
CH3
Ph
C
C
CH3
CH3
14
The decreasing order of reactivity of the compounds given below towards solvolysis under
identical conditions is :
Cl
Cl
|
|
CH3 – C – CH3
CH3 – C – CH3
Cl
|
CH3 – C – CH3
H3C
(a) II > III > I
(III)
(II)
(I)
(b) I > II > III
(c) III > II > I
(d) II > I > III
OH
1. One Eq. NaOH
63.
(A); Product (A) is :
OH ¾¾¾¾¾¾¾¾®
2. MeBr
(a)
64.
OH
OH
OMe
OH (b)
OMe (c)
(d) None of these
( R )-2-octyl tosylate is solvolyzed in water under ideal S N1 conditions. The product(s) will
be:
(a) R-2-octanol and S-2-octanol in a 1 : 1 ratio
(b) R-2-octanol and S-2-octanol in a 1.5 : 1 ratio
(c) R-2-octanol only
(d) S-2-octanol only
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65.
66.
From each of the following pairs select the compound that will react faster with sodium
iodide in acetone :
Pair-A: (1) 2 - Chloropropane
(2) 2 - Bromopropane
Pair-B: (3) 1 - Bromobutane
(4) 2 - Bromobutane
(a) 1, 3
(c) 2 , 3
(b) 1, 4
(d) 2 , 4
Among the given halides, which one will give same product in both S N1 and S N 2 reactions.
CH 3
CH3
|
(I) CH 3 - CH - CH 2 - CH - CH 3
(II)
|
Cl
Br
Cl
67.
(III)
(IV) CH 3 - CH - Br
(a) (III) only
Et
(c) (III) & (IV)
|
(b) (I) & (II)
(d) (I), (III) & (IV)
Product(s) formed during this reaction is/are :
*
CH2 – CH2 – OTs
AcONa
AcOH
¾ ¾¾
¾® Product ? [ C * = isotopic carbon]
* – OAc
CH2 – CH
2
* – CH – OAc
CH
2
2
(a)
(b)
*
CH2 – CH2 – OTs
(c)
(d) Both (a) & (b)
OAc
68.
69.
HI (conc.)
Anisole ¾ excess
¾¾¾¾¾¾® Product
reflux
(a)
I + CH3I
(b)
I + CH 3OH
(c)
OH
(d)
OH
+ CH 3I
+ CH 3CH2I
Which of the following compounds would react faster with NaCN in an S N 2 reaction ?
OMe
(a)
(b)
OTs
(c) MeO
(d)
OTs
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70.
HC ºº CNa + Cl – CH 2 – CH 2 – CH 2 – I ¾® (A); Major product (A) is :
(a) H – C º C – CH 2 – CH 2 – CH 2 – I
(c) H – C º C – CH 2 – CH 2 – CH 2 – Cl
71.
What is the major product obtained in the following reaction ?
Et2O
Product.
SNa + CH3 — Br
(a)
72.
Br
CH3
H
H
(a)
Br
(b)
HO
S
S
(c)
CH3
2
CH3
H
(d)
N
+ OH - ¾ ¾
¾® A; The product A is :
CH3
H
(b) HO
H
(c) Both (a) and (b) are correct
73.
(b) CH 2 = CH – CH 2 – I
(d) CH 2 = CH – CH 2 – Cl
H
(d) None is correct
H 2O
Me 2 C = CH – CH 2 – CH 2 – Cl ¾¾¾¾® ( X ); Major product of the reaction is :
CaCO 3
OH
|
(a) Me – C – CH 2 – CH 2 – CH 2
|
Me
(b) Me 2 C = CH – CH 2 – CH 2 – OH
OH
(c) Me 2 C = CH – CH – CH 2 – OH
|
OH
OH
(d)
OH
HBr
74.
CMe2
HBr
¾ ¾¾® ( A) ,
¾ ¾¾® ( B )
D
D
OCH3
CH2OH
Product (A) and (B) respectively are :
OH
(a)
OH
(b)
and
CH2Br
OH
Br
OH
and
CH2Br
OH
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283
OH
(c)
OH
and
OCH3
CH2OH
Relative rate of reaction with H 2 O.
H
H
ONS
CH3
(ii)
O
æ
ç
||
ç —ONS == —O — S
ç
||
ç
O
è
(a) (i) > (ii) > (iii)
(c) (iii) > (ii )> (i)
O
ONS
CH3
(i)
O
H
ONS
CH3
2 eq. KNH
n—C H — Br
NH 3 ( l )
then H 3O Å
(iii)
ö
÷
NO 2 ÷
÷÷
ø
(b) (ii) > (i) > (iii)
(d) (iii) > (i) > (ii)
2
4 9
¾ ¾¾¾¾
® ¾ ¾¾¾¾¾
® (P) ;
76.
End product (P) of the above reaction is :
O
O
O
(a)
O
(b)
O
O
O
(c)
77.
Br
(d)
and
CH2Br
75.
Br
Br
O
(d)
Which of the following statements is correct regarding the rate of hydrolysis of the
compounds (A) and (B) by S N1 reaction ?
Br
A
O
Br
B
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(a) A reacts faster than B
(c) Both A and B reacts at the same rate
78.
(b) B reacts faster than A
(d) Neither A nor B reacts
What are reactant X and product Y in the following sequence of reactions ?
O
H3C
O
SCl
O
Reactant X
H3C
Pyridine
H
Reactant X
(a)
OH
H3C
(d)
O
Product Y
H
N3
H
OH
H
H3C
N3
H
H
H3C
H
H
H
N3
OH
H
79.
H
OH
H3C
H
NaN3
Ethanol-water
N3
H
H
(c)
H
CH3
S
Product Y
H
(b)
O
H
H
Transition state of given S N 2 is :
CH2—Br
CH2—O—R
R-O–
SN2 reaction
+
+
ds
+
+
d (+)
OR
OR
H
(a)
H
(b)
H
H
Br
Br
dr
d (+)
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+
+
dr
OR
OR
H
H
(c)
(d)
H
H
Br
Br
ds
80.
d (–)
C 6 H 13 Br + OH - ¾® C 6 H 13 OH + Br - is an example of:
(a) Nucleophilic addition
(c) Electrophilic addition
(e) Free radical substitution
81.
+
+
d (–)
(b) Nucleophilic substitution
(d) Electrophilic substitution
Transition state 2 is structurally most likely as :
T.S.2
T.S.3
intermediate 2
T.S.1
E
intermediate 1
product
reactant
(a) intermediate 1
(c) intermediate 2
(b) transition state 3
(d) product
O
CH2
82.
O
O
x = Number of aromatic compound obtained when above compound undergo complete
acidic hydrolysis.
(a) 1
(b) 2
(c) 3
(d) 4
83.
S N 1 and S N 2 reactions are
(a) Both stereospecific
(b) Both stereoselective
(c) Stereoselective and stereospecific respectively
(d) Stereospecific and stereoselective respectively
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84.
Most reactive compound toward S N 1 is :
(a)
(b)
CH2—I
CH2—I
CH2—I
CH2—I
(c)
(d)
CH
C
1. NaNH 2 ( 2 eq.)
2. CH 3CH 2 — I
85.
¾ ¾¾¾¾¾¾® Product ( X ) is :
3. CH 3 — I
4. H 2 / Pd - BaSO 4
OH
CH3CH2
CH3CH2
(a)
(b)
OCH3
CH2—O—CH3
CH3
CH3
(c)
(d)
O—CH2CH3
CH2—OCH2CH3
86.
Following reaction is an example of :
O
+ R2NH
(a) S N 2 Reaction
(b) S N 1 Reaction
(c) Electrophilic Addition
(d) S N – NGP
87. The major product of the following reaction :
OH
|
HBr
[x]
(a)
Br
|
H
|
(b)
(d)
Br
88. Choose the suitable option for the correct mechanism for the following reactions.
(I)
+
Br
CH3O
(c)
CH3OH
+ CH3OH
(II)
high
concentration
OH
Br
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(a) S N 1, S N 1
(b) S N 1, S N 2
(c) S N 2, S N 1
O
O
H+
89.
O
HO
(d) S N 2, S N 2
Reaction 1
OMe
O
O
O
O
O
N3–
O
Reaction 2
N3
Br
Types of mechanism followed by reaction 1 and reaction 2 respectively.
(a) S N 1, S N 1
(b) S N 2, S N 2
(c) S N 1, S N 2
(d) S N 2, S N 1
90.
OTs
OTs
H2S
Product
KOH
Product of above reaction will be :
OTs
(a)
(b)
SH
(d)
(c)
S
OTs
SH
S
ANSWERS — LEVEL 1
1.
(a)
2.
(b)
3.
(c )
4.
(a)
5.
(b)
6.
(b)
7.
(b)
8.
(d)
9.
(b)
10.
(a)
11.
(c)
12.
(a)
13.
(d)
14.
(d)
15.
(b)
16.
(c)
17.
(a)
18.
(a)
19.
(c)
20.
(d)
21.
(b)
22.
(a)
23.
(c)
24.
(c)
25.
(d)
26.
(d)
27.
(d)
28.
(a)
29.
(a)
30.
(d)
31.
(b)
32.
(d)
33.
(d)
34.
(c)
35.
A(a)
35.
B(b)
36.
(d)
37.
(b)
38.
(d)
39.
(b)
40.
(d)
41.
(d)
42.
(a)
43.
(c)
44.
(b)
45.
(c)
46.
(d)
47.
(a)
48.
(b)
49.
(b)
50.
(d)
51.
(b)
52.
(d)
53.
(a)
54.
(b)
55.
(a)
56.
(a)
57.
(b)
58.
(c)
59.
(c)
60.
(b)
61.
(c)
62.
(d)
63.
(a)
64.
(b)
65.
(c)
66.
(d)
67.
(d)
68.
(c)
69.
(d)
70.
(c)
71.
(c)
72.
(b)
73.
(d)
74.
(b)
75.
(c)
76.
(d)
77.
(b)
78.
(b)
79.
(d)
80.
(b)
81.
(c)
82.
(b)
83. (b,c)
84.
(d)
85.
(b)
86.
(a)
87.
(c)
88.
(c)
89.
(c)
90.
(b)
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288
Level - 2
1. Statement-1 : Nucleophilicity order in polar-protic solvent is I - < Br - < Cl - < F Statement-2 : Due to bigger size of I - it is less solvated in polar-protic solvent.
(a) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for
statement-1.
(b) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation
for statement-1.
(c) Statement-1 is true, statement-2 is false.
(d) Statement-1 is false, statement-2 is true.
2. Statement - 1 : CH 3 - CH 2 - Cl + NaI ¾ Acetone
¾¾¾® CH 3 - CH 2 - I + NaCl ¯
Statement- 2 : Acetone is polar-protic solvent and solubility order of sodium halides
decreases dramatically in order NaI > NaBr > NaCl. The last being virtually insoluble in this
solvent and a 1º and 2º chloro alkane in acetone is completely driven to the side of
Iodoalkane by the precipitation reaction.
(a) Statement-1 is true, Statement-2 is true and Statement-2 is correct explanation for
statement-1.
(b) Statement-1 is true, Statement-2 is true and Statement-2 is Not the correct explanation
for statement-1.
(c) Statement-1 is true, Statement-2 is false.
(d) Statement-1 is false, Statement-2 is true.
3. Encircle whichever of the following :
(a) is the stronger nucleophile (aprotic solvent) : F - or I (b) is the stronger nucleophile (protic solvent) : F - or I (c) is the stronger base : F - or I (d) is the stronger nucleophile (protic solvent) : NH3 or NH 2 NH 2
(e) is the better leaving group : CH 3 COO - or CH 3 SO 34. Encircle whichever of the following :
Br
|
(a) undergoes an S N 2 reaction more rapidly, CH 3 - Br or CH 3 - CH - CH 3
Br
|
(b) undergoes an S N1 reaction more rapidly, CH 3 - Br or CH 3 - CH - CH 3
(c) undergoes an E 2 reaction to give (Z)-1,2-diphenylpropene :
Ph
Ph
H
Br
H
CH3
Ph
or
Br
Ph
H
Ph
C=C
CH3
H
H
CH3
Ph
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(d) reacts with NaI to give (Z)-1,2-diphenylpropene :
Ph
Ph
H
Br
Br
(e) undergoes an S N1
CH3
or
Br
H
Br
CH3
Ph
Ph
reaction more rapidly,
Br
Br
or
5. Encircle whichever of the following :
CH2–Br
(a) undergoes an S N 2 reaction more rapidly :
(b) undergoes an E 1 reaction more rapidly :
CH3
or
Br
CH3
|
C–CH2–CH3
CH3
|
CH–CH2–CH2
|
Br or
Br
Br
(c) undergoes an S N1 reaction more rapidly:
or
Br
Cl
(d) undergoes an S N 2 reaction more rapidly:
Cl
or
Cl
Cl
(e) undergoes an E 2 reaction more rapidly :
or
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6. Match the column :
Relative rate
Alkyl halide
Relative rate
(S N 2 )
(S N1 )
(a)
CH 3 – Br
(p)
1
(w)
1200
(b)
CH 3 - CH 2 – Br
(q)
1.05
(x)
40
(c)
CH 3 - CH - Br
|
CH 3
(r)
11
(y)
16
(d)
CH 3
|
CH 3 - C - Br
|
CH 3
(s)
1,200000
(z)
1
7. Matrix :
Column (I)
Column (II)
Compound
Type of reaction
Cl
(p) S N1 reaction can take place
(a)
Cl
(q) S N 2 reaction can take place
(b)
Cl
(r) S N1 is not possible
(c)
Cl
(d)
(s) S N 2 is not possible
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8. Encircle whichever of the following :
Br
(a) undergoes an S N 2 reaction more rapidly,
or
Br
(b) undergoes an S N1 reaction more rapidly, (CH 3 ) 3 C - Br or (CH 3 ) 3 C - I
Br
Br
(c) undergoes an S N1 reaction more rapidly,
or
9. Reactivity : Circle the reaction that reacts FASTER by S N 2 in each pair :
(1)
OH -
3
Cl ¾ NaOCH
¾¾¾
® (2)
3
Br ¾ NaOCH
¾¾¾
®
I ¾ ¾¾® (3)
Cl ¾ NaOH
¾¾
¾®
I ¾ NaOH
¾¾
¾®
Cl ¾ NaOH
¾¾
¾®
10. Consider the potential energy diagram given below
B
E nerg y
D
C
A
E
F
Reaction Progress
(X) Name the positions A-D
(Y) Answer the following questions .
(i) Both reaction pathways are :
EXOTHERMIC or
ENDOTHERMIC
(ii) Which step is the rate determining step (RDS) ?
B
or
D
(iii) Which product is most stable ?
E
or
F
(iv) In accordance with Hammonds postulate, exothermic reactions tend to have
(a) early transition states that are reactant - like
(b) late transition states that are reactant-like
(c) early transition states that are product-like
(d) late transition states that are product-like.
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11.
Select whether the following combinations of reactants will react by substitution (S N1 or S N 2
mechanism), elimination (E 1 or E 2 mechanism)
Br
A.
NaI in acetone
¾¾¾¾¾¾®
25°C
(a) S N1
(b) S N 2
Cl
B.
(c) E 1
(d) E 2
(c) E 1
(d) E 2
(c) E 1
(d) E 2
(c) E 1
(d) E 2
(c) E 1
(d) E 2
(c) E 1
(d) E 2
NaOCH 3 in methanol
¾¾¾¾¾¾¾®
50°C
(b) S N 2
(a) S N1
Cl
C.
NaOCH 3 in methanol
¾¾¾¾¾¾®
25°C
(a) S N1
(b) S N 2
D. (CH 3 ) 3 C - OH
¾¾¾¾¾¾®
(a) S N1
(b) S N 2
E. (CH 3 ) 2 CH - Br
¾¾¾¾¾¾¾®
(a) S N1
(b) S N 2
H
F.
(a) S N1
HBr 48% in H 2O
25°C
NaCN in ethanol
25°C
H
Br
NaCN in ethanol
¾¾¾¾¾¾¾®
25°C
(b) S N 2
G. (CH 3 ) 2 CHCH 2 CH 2 - OH
(a) S N1
(b) S N 2
HBr 48% in H 2O
¾¾¾¾¾¾¾®
50°C
(c) E 1
(d) E 2
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293
12.
Examine the ten structural formulas shown in fig. & select that satisfy each of the following
conditions. Write one or more (a through j) in each answer box.
(a)
Br
(b)
CH 3
|
H 3 C — C — Cl
|
CH 3
(c)
Cl
CH2 – Br
(d)
CH 3 - I
CH 3
|
(g) H 3 C — C — CH 2 — Cl
|
CH 3
Cl
(e)
(f)
H2C
(h)
CH2 – Br
CH2 — Cl
C
|
CH3
Br
(i)
(j)
A.
Which compounds give an S N 2 substitution reaction on treatment with alcoholic NaSH ?
B.
Which compounds give an E 2 elimination reaction on treatment with alcoholic KOH ?
C.
Which compounds do not react under either of the previous reaction conditions ?
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294
13.
Select which reaction from the following reaction pairs will occur faster.
PART - 1
OH
I
CH3
Reaction A
CH3
H O
¾ ¾2¾®
DMSO
OH
I
Reaction B
H
H
H O
¾ ¾2¾®
DMSO
PART - 2
I
Cl
Reaction C
NaI
CH3 ¾ ¾
¾®
DMSO
CH3
CH2I
CH2Cl
¾ NaI
¾
¾®
Reaction D
DMSO
PART - 3
Cl
I
NaCl
H ¾ ¾¾®
Reaction E
H
DMSO
Cl
I
Reaction F
H
¾ NaCl
¾¾®
PART - 4
I
Reaction G
Reaction H
H
EtOH
N3
NaN 3
H ¾ ¾¾®
H
Br
N3
DMSO
NaN 3
H ¾ ¾¾®
H
DMSO
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PART - 5
CH2 — I
CH2 — Cl
Reaction I
¾ NaI
¾
¾®
acetone
Br
I
Reaction J
¾ NaI
¾
¾®
acetone
CH3
14.
CH3
Tick your answer in the given box.
Expect S N 2
Alkyl Halide
2-D Structure
(at a reasonable rate)
Yes
(a)
1-Bromobutane
No
Br
Yes
(b)
1- Chlorobutane
No
Cl
Br
(c)
Yes
2-Bromobutane
No
Cl
(d)
Yes
2-Chlorobutane
No
Yes
(e)
2-Chloro-2-methyl propane
Cl
No
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Br
(f)
Yes
Bromocyclohexane
No
Br
(g)
Yes
Bromobenzene
No
CH2 – Br
(h)
Yes
Benzyl bromide
No
(i)
1-Bromo-2,2-dimethyl
propane
Yes
Br
No
Yes
(j)
Bicyclo compound
Br
No
Br
Yes
(k)
1-bromotriptycene
No
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297
15.
Match the column
Column-I
Column-II
Cl
(a)
(p) It will undergo Nucleophilic Substitution
reaction
(b)
(q) It will undergo E 2 reaction
CH2—Cl
CH3
C—Cl
(c)
(r) It will undergo E 1 reaction
CH3
F
(d)
NO2
(s) It will undergo S N 2 reaction
(t) It will undergo S N 1 reaction
16.
O
O—Et
xHI
¾¾
¾®
O
O—Et
How many (x) moles of HI consumed?
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298
17.
Column (I)
(a)
Ph
Column (II)
H O
2
Cl ¾¾®
Cl
(b)
sr
Ph—SNa
¾¾¾¾®
(p)
SN1
(q)
SN 2
(r)
Carbocation is intermediate
(s)
Carbanion is intermediate
F
KOH
¾¾¾®
D
(c)
NO
(d)
Br
2
¾¾¾®
CCl
4
18.
Column (I)
Column (II)
(Reaction sequence)
(a)
s
O ¾®
(b)
Br ¾®
(c)
¾®
(d)
Et — Cl ¾®
OEt
(Reagent required)
(p)
(q)
OEt
(r)
(s)
EtO
s
EtBr
EtOH/H
r
Et–Cl/Na ether
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299
19.
Choose the one compound within each set that meets the indicated criterion :
Column (I)
Column (II)
(a) The compound that reacts with alcoholic
KOH to liberate Halide ion through
(p)
substitution reaction.
F
O2 N
CH3
(b) The compound that cannot be prepared by
(q)
a Williamson ether synthesis.
(c) The compound that gives an acidic solution
when allowed to stand in aqueous ethanol.
(r)
OC2H5
O
F
Br
(d) The ether that cleaves more rapidly in HI.
(s)
—C—CH3
CH3
20. Comprehension
The first demonstration of the stereochemistry of the S N 2 reaction was carried out in 1935 by
Prof. E.D. Hughes and his colleagues at the University of London. They allowed
(R)-2-iodooctane to react with radioactive iodide ion (*I–).
CH3CH(CH2)5CH3 + *I –
CH3CH(CH2)5CH3 + I –
*I
I
2-iodooctane
2-iodooctane
(radioactive)
The rate of substitution (rate constant K s ) was determined by measuring the rate of
incorporation of radioactivity into the alkyl halide. The rate of loss of optical activity from
the alkyl halide (rate constant K o ) was also determined under the same conditions.
What ratio K o / K s is predicted for each of the following stereochemical scenarios :
A. For inversion reaction :
K
K
(a) o = 1
(b) o < 1
Ks
Ks
Ko
>1
Ks
(d) can not be predicted
B. For equal amounts of both retention and inversion ?
K
K
K
(a) o = 1
(b) o < 1
(c) o > 1
Ks
Ks
Ks
(d) can not be predicted
(c)
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ANSWERS — LEVEL 2
1.
d
2.
c The reaction is Finkelstein reaction.
3.
(a)
F– ;
(b)
I–
; (c)
F– ;
(d) NH —NH
2
2
;
(e)
CH3SO3–
Ph
Br
|
4.
(a) CH 3 - Br
(b) CH 3 - CH - CH 3
(c)
H
Br
H
CH3
Ph
Ph
H
(d)
Br
Br
Br
CH3
(e)
Ph
CH
|
C–CH2–CH3
5.
(a)
CH2–Br
Br
(b)
Br
(c)
Cl
Cl
(d)
(e)
6.
a – p, w; b – q, x ; c – r, y; d – s, z
7.
a – r, s; b – p, q; c – r, s; d – r, s
8.
(a)
Br
(b) (CH 3 ) 3 C - I
(c)
Br
9.
10.
(1)
Br
(2)
I
(3)
Cl
(X) A- reactants, B-transition state, C-Inter mediate, D- transition state
(Y) (i) exothermic (ii) B (iii) F (iv) a
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11.
A – b; B – b; C – d; D – a; E – b; F – b; G – b
12.
A – c, d, e, f, h; B – b, c, f, i ; C – a, g, j
13.
Part –
1
2
3
4
5
Reaction–
A
D
E
G
I
Yes –
a,
b,
c,
d,
f,
h,
No –
e,
g,
i,
j,
k
14.
15.
a–p, q, r, s, t; b–p,s,t; c–p, q, r t; d–p
16.
2
17.
a – p, r;
18.
a – q; b – p; c – r; d – q
19.
a – p; b – r; c – s; d – s
20.
A – c; B – a
b – q;
c – s;
d–r
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302
5B
ALKYL HALIDES
Elimination Reactions (E1 , E 2 , E1CB , Ei )
Level - 1
1.
Which of the following alkyl halide gives only one product (excluding stereoisomer) when
undergo E 2 reaction ?
(E 2 = elimination bi-molecular)
Cl
(a)
Cl
(b)
(c)
(d)
Cl
Cl
X
E2 reaction
2.
+
(Hoffmann product)
(Saytzeff product)
(A)In the above reaction, maximum Saytzeff product will obtained when :
(a) X = -I
(b) X = -Cl
(c) X = -Br
(d) X = -F
(B) In the above reaction Hoffmann product is major when X is :
(a) -I
(b) – Cl
(c) – Br
(d) – F
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3.
O
N
|
303
H (P)
when (P) undergoes Hoffmann exhaustive methylation (twice) then the product obtained
will be :
H
|
O
N
(a)
(b)
(c)
(d)
OO
NMe2
+
4.
NMe2
heat
heat
¾ ¾¾® ( B ) ,
¾ ¾¾® ( A),
Ei
Ph
98%
(syn)
Ei
Ph
85%
(Anti)
Ph
Ph
(P)
(Q)
Product (A) & (B) of the above reaction is :
(a) A = P , B = P
(b) A = Q , B = Q
(c) A = P , B = Q
CH3
HO–
5.
D
(d) A = Q , B = P
Major product of the reaction is :
OTs
(a)
6.
(b)
(c)
(d)
Which of these dehydrates most easily ?
(a) CH 3 — CH 2 — CH 2 — OH
(b)
CH3
OH
CH 3
|
OH
(c)
(d) CH 3 — C — CH 2 — OH
|
CH 3
CH3
NaOCH 3
¾ ¾¾¾¾
¾® Product; Product of the reaction is :
7.
Br
CH 3OH
(E 2 reaction)
CH3
(a)
(b)
(c)
(d) No reaction
OCH3
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304
NMe3
HO-
8.
A
D
(Major)
Major product A is :
(a)
(b)
(c)
(d)
(c)
(d)
OH
H2SO4
9.
D
A
(Major)
Major product A is :
(a)
10.
(b)
In which of the following reaction Saytzeff alkene is major product ?
CH 3
|
Å
-
HO
(a) CH 3 - CH 2 -C - NMe 3 ¾ ¾¾
®
D
|
-
EtO
(b) CH 3 - CH 2 - CH 2 - CH - CH 3 ¾ ¾¾
®
D
|
CH 3
F
CH 3
Br
|
(c) CH 3 - CH 2 -C
|
t - BuOK
- CH 3 ¾ ¾¾
¾®
D
|
3OK
(d) CH 3 - CH 2 - CH 2 - C - CH 3 ¾CH
¾¾
¾®
|
D
CH 3
Br
CH3
11.
Ph
H
alc. KOH
Ph
Br
(E2 reaction)
Major product of the reaction is :
CH3
Ph
(a)
C=C
Ph
CH3
(c)
12.
(b)
CH3
Ph
(d)
C=C
Ph
Ph
CH3
CH3
C=C
CH3
Ph
CH3
Ph – CH - CH - Ph
|
|
CH 3 OH
The conversion of 2, 3-dibromobutane to 2-butene with Zn is :
(a) Redox reaction
(b) a-Elimination
(c) b-Elimination
(d) Both a-elimination and redox reaction
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305
13.
1, 3-Dibromopropane is heated with zinc dust in ether. The product formed is :
(a) propene
(b) propane
(c) cyclopropane
(d) 3-bromopropane
O
Br
14.
alc. KOH
Reaction (1)
¾ ¾¾¾® (A) (major)
O
alc. KOH
Reaction (2)
¾ ¾¾¾® (B) (major)
Br
O
alc. KOH
Reaction (3)
¾ ¾¾¾® (C) (major)
Br
Product obtained in above reactions (1), (2) & (3) is :
(a) A = B but C is different
(b) A = C, but B is different
(c) B = C, but A is different
(d) A = B = C all product are identical
Cl
15.
Cl
Cl
Reaction (1) Cl
Cl
3 mole alc. KOH
¾ ¾¾¾¾¾
¾® (A)
Cl
Cl
Cl
Cl
Reaction (2) Cl
Cl
3 mole alc. KOH
¾ ¾¾¾¾¾
¾® (B)
Cl
Cl
Cl
Cl
Reaction (3) Cl
Cl
3 mole alc. KOH
¾ ¾¾¾¾¾
¾® (C)
Cl
Product obtained in above reactions (1), (2) & (3) is :
(a) A = B, C is different
(b) A = C, B is different
(c) B = C, A is different
(d) A = B = C is same
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alc. KOH
16.
( x)
¾¾¾®
x is number of E 2 product obtained
(including stereoisomers)
Br
Find (x).
(a) 3
17.
(b) 4
CH 3
|
EtOH
( A)
CH 3 ¾ C ¾ CH ¾ CH 3 ¾¾¾®
D
| |
CH 3 Br
(c) 5
(d) 6
(c)
(d)
Major product (A) is :
(a)
18.
19.
(b)
Which one of the following compound will be least susceptible to elimination of hydrogen
bromide ?
(a) Br — CH 2 — CH 2 — NO 2
(b) Br — CH 2 — CH 2 — CH 3
(c) Br — CH 2 — CH 2 — CN
(d) Br — CH 2 — CH 2 — CO 2 Et
Two alkenes, X(91% yield) and Y(9% yield) are formed when the following compound is
heated.
CH3
D
¾¾® X + Y
91%
N(CH3)3OH
9%
The structures of X and Y, respectively are :
20.
(a)
CH3 and
CH2
(b)
CH3 and
CH3
(c)
CH2 and
CH3
(d)
CH3 and
CH2
In the dehydrohalogenation of 2-bromobutane; which conformation leads to the formation
of cis-2-butene ?
CH3
CH3
CH3
CH3
H
H
CH3
CH3
H
CH3
H
H
(a)
(b)
H
Br
(c)
H
O–H
H
Br
CH3
H
H
Br
H
O
CH3 – C – Cl (2 mole)
21.
H
Br
(d)
Pyridine
(A)
(Ei)
D
(B) + CH 3CO2H
O–H
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307
Product (B) of given reaction is:
(a)
22.
(b)
(c)
(d)
What product will be formed from Hoffmann exhaustive methylation of following compound?
(i) CH 3 - I (excess)
Me 2 CHCH 2 NHCH 2 CH 2 Me ¾¾¾¾¾¾® Product
(ii) Ag 2O
(iii) D
(a) Me — CH == CH 2
(b) H 2 C == CH 2
(c) CH 3 — C == CH 2
|
CH 3
(d) CH 3 — CH — CH == CH 2
|
Me
CH2
OH
Hr
( A)
¾¾®
D
23.
Product (A) is :
(a)
(b)
(c)
(d)
(c) G.I
(d) Positional isomers
CH 3
Hr
¾¾®
; Products obtained are :
D
24.
OH
(a) Racemic
(b) Diastereomers
CH3
NaOEt
25.
¾¾¾¾¾® ; Major product of the reaction is :
(E 2reaction)
Cl
CH3
(a)
CH3
(b)
CH3
(c)
CH3
(d)
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CH3
NaOEt
Cl ¾¾¾® ; Major product of the reaction is :
26.
CH3
CH3
(a)
27.
CH3
(b)
CH3
(c)
(d)
The E 2 product of the following reaction will be ?
CH3
H
NaOH
H
Br
H
OH
CH3
(a)
OH H
(c)
28.
29.
CH3
(b)
H
CH3
H
CH3
(d)
H
An halide C 5 H 11 Br on treatment with alc. KOH give 2-pentene only. The halide will be :
(a) CH 3 - CH 2 - CH 2 - CH 2 - CH 2 - Br
(b) CH 3 - CH 2 - CH 2 - CH - CH 3
|
Br
CH 3
|
(c) CH 3 - CH 2 - CH - CH 2 - CH 3
(d) CH 3 - CH - C - CH 3
|
|
Br
Br
End product (D) in the given sequence is:
Br
CH 3 NHCH 3
BaO
CH 3 I
(2molar equivalent)
Ag 2O H 2O
( A) ¾¾®( B ) ¾¾¾¾¾¾®(C ) ¾¾¾®( D) + (CH 3 ) 3 N
Br 2¾¾¾¾¾®
molar equivalent
CH3
O
(a)
(b)
(c)
(d)
O
OH
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30.
For each of the following pairs of E 2 reaction, select the one that occurs with the greater rate
constant.
CH 3
CH 3
|
|
(2) CH 3 CH 2 CH 2 I + CH 3 - C - O (1) CH 3 CH 2 CH 2 Cl + CH 3 - C - O |
|
CH 3
CH 3
(3) H 3 C - CH - CH 3 + CH 3 O |
Br
(5)
31.
Br
(4) H 3 C - CH - CH 3 + CH 3 S |
Br
Br
+ –OH`
+ –OH
(6)
(a) 2, 4, 6
(b) 1, 3, 5
(c) 2, 3, 5
(d) 2, 4, 5
Br Br
|
|
y CH 3 I
xNaNH 2
CH 3 ¾ C ¾ C ¾ CH 3 ¾¾¾® ¾¾¾® CH 3 ¾ C ºº C ¾ C ºº C ¾ CH 3
|
|
Br Br
x and y mole consumed.
Value of x + y =
(a) 5
32.
(b) 6
(c) 7
(d) 8
The following bimolecular elimination reaction (E 2 ) is carried out with different halogen
leaving groups. The per cent yield of the two products (2-hexene and 1-hexene) for each
leaving group is listed below.
X
Leaving group
+ CH3O–
E2
Conj. Acid pK a
+
%-yield of 2-hexene
%-yield of 1-hexene
X =I
– 10
81%
19%
X = Br
–9
72%
28%
X = Cl
–7
67%
33%
X =F
3.2
30%
70%
Which of the following statement is (are) true concerning this series of E 2 reactions ?
(a) Based on the pK a 's of the conjugate acid, I - is the best leaving group and F - is the
poorest leaving group
(b) When I - , Br - and Cl - are used as leaving groups, Zaitsev's rule is followed
(c) F - is the strongest base (and therefore the poorest leaving group) and the transition
state for reaction with fluoride as the leaving group has the least double bond character
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(d) a, b, c are true
N(CN3)2
33.
I
H3 –
(1) C
g O
(2) A 2
(3) D
A
H
(1) H
(2) D 2 O2
D
B
Product ( A) & ( B ) respectively are :
H
(c)
H
D
H
H
&
H
N Me
34.
H
H
&
(a)
(b)
H
&
H
D
H
H
H
&
(d)
D
D
(1) MeI
(2) AgOH
conc. H 2SO 4
(1) MeI
OH ¾¾¾¾®
( A) ¾¾¾¾® ( B ) ¾¾¾¾® (C)
(3) D
(2) AgOH
(3) D
Product in above reaction is :
Me – N – Me
(a)
(b)
(c)
(d)
35.
Major product obtained in the reaction of 1-phenyl-2-bromobutane with NaOMe is :
(a) (E)-1-phenylbut-1-ene
(b) (E)-1-phenylbut-2-ene
(c) 1-phenyl-2-ethoxybutane
(d) (Z)-1-phenylbut-2-ene
36.
Which of the following alkyl halides give most complex mixture of alkene in an E 2 reaction ?
(a) CH 3 - CH 2 - CH 2 - CH 2 - Br
(b) CH 3 - CH 2 - CH 2 - CH - CH 3
|
Br
(c) CH 3 - CH 2 - CH - CH 2 - CH 3
|
Br
CH3
37.
H
Br
H
CH 3
|
(d) CH 3 - C - CH 2 - CH 3
|
Br
D
alc. KOH
H ¾ ¾¾¾
® ( A)
(major)
Product (A) is :
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311
OH
D
H
(a)
OH
38.
CH3
D
(b)
D
(c)
(d)
OH
Hr
( B)
¾¾®
D
Hr
( A) ;
¾¾®
D
Sum of number of a-hydrogen present is compound A + B is :
(a) 18
(b) 19
(c) 20
39.
( A)
(i) excess CH 3 I K 2CO 3
(ii) Ag 2O
¾ ¾¾¾¾¾¾¾¾® ( B ) ¾ ¾¾¾¾¾¾¾® H 2 C
(iii) D
(2) Ag 2O H 2O
(3) D
(1) excess CH 3 I K 2CO 3
(d) 21
= CH -CH - CH = CH 2
|
CH 3
Identify A :
(a)
(b)
(c)
N
|
H
40.
(d)
N
|
H
N
|
H
N
|
H
Br
|
alc. KOH
CH 3 — CH 2 — C — CH 2 — Et ¾ ¾¾¾® ( A)
(major)
|
CH 2 (n - Pr)
n - Pr = n - propyl
Product (A) is :
Me
Et
Me
(a)
(b)
Pr
H
Me
Et
Et
(c)
H
Pr
Me
Et
(d)
Pr
Pr
Ph
OH
41.
H PO
3
4
¾ ¾¾
¾
® Major product obtained by dehydration of given alcohol is :
D
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312
Ph
Ph
(a)
(b)
Ph
Ph
(c)
(d)
Br
Å
NaOCH 3 (2 mole)
H 3O
O ¾ ¾¾¾¾¾
¾® ( A) ¾ ¾¾
¾® ( B )
42.
CH 3OH
Br
Product (B) of above reaction is :
OH
OH
OH
OH
(a)
(b)
(c)
OH
43.
(d)
OH
OCH3
Zn -Cu
Ph — CH — CH 2 — CH 2 ¾ ¾¾
¾® Product
D
|
|
Br
Br
Product of the above reaction is :
(a) Ph — CH == CH — CH 2 — Br
(c) PH — CHBr — CH == CH 2
OH
44.
(b) Ph
(d) Ph — C ºº C — CH 3
Hr
¾¾®
( A)
D
OH
Product (A) is :
(a)
(b)
(c)
(d)
H
H
Ph
45.
NaOEt
Me
Ph
¾ ¾¾
¾®
D
NMe3
Major product of the above reaction is :
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(a)
Ph
Ph
Ph
(c)
(b)
C == C
H
(d)
C == C
Me
Ph
Me
Me
Me
C == C
Ph
LDA
46.
Ph
C == C
Ph
Ph
Ph
Ph
OEt
A + N2 + Ph – CH = CH2 , Product A is:
N
NH — CH2 — CH2 — Ph
LDA = Lithium di-isopropyl amide
(a)
(b)
(c)
(d)
N
|
H
47.
Major product of the reaction, when the given compound undergoes Hoffmann exhaustive
methylation is :
(a)
(b)
CH3
(c)
(d) H 2 C == CH 2
H
H
48.
POCl 3
¾ ¾¾¾® Major product of the reaction is :
Pyridine
H
H
OH
CH3
(a)
(b)
CH3
H
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CH3
H
H
(c)
(d)
Ph
H
H
Cl
Ph
C = CH – C – OH
H+
D
49.
¾¾
¾® Product
Stereochemistry of the product is :
(a) Meso compound
(c) Diastereomer
CH3
50.
(b) Racemic mixture
(d) Optically pure enantiomers
O
O
Which of the following reactant is used to obtain above compound (A). (Assume that EtO - is
used in all the reaction)
CH3
Br
Br
H
H
CH3 Br
CH3
Br
CH3
H
H
(a)
(b)
(c)
(d)
O
O
O
O
O
O
O
O
H
51.
Cl
OH
H
H
H
alc. KOH
¾ ¾¾¾
¾® ( A), Product A is :
O
OH
(a)
O
(b)
(c)
(d)
Cl
52.
Rank the following in order of decreasing rate in an E 2 reaction:
CH3
CH3
CH3
Br
Br
Br
(a)
(a) a > b >c
CH3
(b)
(b) c > a > b
(c)
(c) c > b > a
(d) b > a > c
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53.
Ph
KOH
EtOH, D
¾ ¾¾¾® ( A) ,
(a) Ph
Product (A) is :
(major)
F
(b) Ph
(c) Ph
(d) Ph
OEt
OH
EtOs
¾¾®
( A) Major
D
54.
Br
EtOs
( B ) Major
¾¾®
D
NMe3
r
Relation between (A) and (B) is :
(a) G.I.
(c) Enantiomer
3NaNH
2
® Product ; The Product is :
Cl ¾ ¾¾¾
liq NH
55.
.
O
(a)
3
(b) HC ºº C — (CH 2 ) 3 ONa
CH2
O
(c) NaC ºº C — (CH 2 ) 3 ONa
56.
(b) Positional isomer
(d) Chain isomer
(d) H — C ºº C — (CH 2 ) 3 OH
Which best describes the product of the following reaction ?
CH3
K +t - BuO -
Ph
(a)
(b)
(c)
(d)
57.
® product
CD3 ¾ ¾¾¾¾
E2
Br
Absolute configuration has been inverted
Absolute configuration has been retained
Racemization (loss of absolute configuration) has occurred
Loss of chirality has occurred (the product is achiral)
What is the major product of the following reaction ?
OH
CH3
|
H+
CH3 – CH2 – C – CH
¾¾
¾® Product
D
|
CH
3
CH3
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CH3
|
CH – CH3
CH3
CH3
C=C
H
CH3
CH3
CH3
|
CH – CH3
H
(c)
C=C
(b)
CH3
H
58.
H
C=C
(a)
CH3
|
CH – CH3
CH3
C=C
(d)
CH3CH2
CH2CH3
CH3
What will be the major product of each of the two reaction shown below ?
heat
1. CH3CH2CHCH3
+N(CH ) –OH
3 3
2. CH3CH2CHCH3+ CH3CH2ONa
Br
(a) 1 – X, 2 – X
NHCH2CH3
59.
CH3CH=CHCH3+CH3CH2CH=CH2
heat
X
(b) 1 – Y, 2 – X
(c) 1 – X, 2 – Y
Y
(d) 1 – Y, 2 – Y
+ CH3I (excess) ¾® product; The product is :
(a) a primary amine
(c) a secondary amine
(b) a tertiary amine
(d) a quaternary ammonium salt
CH2–OH
H+
60.
Isomerisation
¾¾
¾® ( A) ¾ ¾¾¾¾
¾®( B )
D
(A) on heating isomerizes to (B). What is the structure of (B) ?
CH3
(a)
OH
(b)
(c)
(d)
H
|
Ph—C—Ph
CH2–CH2–OH
61.
+
H
¾¾
¾® ( A) , major product (A) is :
D
(major)
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Ph—C—Ph
Ph—CH—Ph
CH2–CH3
(a)
CH–CH3
(b)
Ph
Ph—CH—Ph
Ph—CH—OH
CH–CH2
CH2–CH3
(c)
(d)
62. Which of the following carbocation will undergo rearrangement ?
CH3
Å
(a)
(b)
Å
Å
Å
(c) CH3 – CH – C = O
|
CH3
(d) CH3 – NH – CH – CH – CH3
|
CH3
63. In which of the following reaction resonance stabilized product will form ?
CH2–OH
OH
H
(a)
+
¾¾
¾
®
D
(b)
H+
¾¾
¾
®
D
CH3
(c)
OH
H+
¾¾
¾
®
D
(d) All of these
64. In which of following reaction rearrangement take place with change in carbon skeleton ?
CH3
|
Å
(a) CH — C — CH
3
2
|
CH3
(b) CH 3 - CH 2 CH 2
Å
(c) CH3 – CH – CH2 – CH2
|
CH3
Å
(d) CH 3 - CH Å - CH 3
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65.
Consider the following reaction :
H3PO4
OH
heat
Which response contains all the correct statement about this process ?
(1) Dehydration
(2) E 2 mechanism
(3) Carbon skeleton migration
(4) Most stable alkene will form
(5) Single-step reaction
(a) 1, 3
(b) 1, 2, 3
(c) 1, 2, 5
(d) 1, 3, 4
CH3
66.
H
Br
H
OH
CH3
(a) cis-2-butene
(c) 1-butene
Br
|
67.
NaI
acetone
HBr
¾ ¾¾® ( X ) ¾ ¾¾¾® (Y) (Major); Product (Y) is:
(b) trans-2-butene
(d) Iso-butene
Br
|
Zn (dust)
CH 2 — CH == CH — CH 2 ¾ ¾¾¾
¾® ( A)
Above reaction is an example of 1,4-elimination. Predict the product.
(a) CH 3 — CH == C == CH 2
(b) CH 3 — C ºº C — CH 3
(c) CH 3 — CH 2 — C ºº CH
(d) H 2 C == CH — CH == CH 2
Ph
conc. H SO
2
4
¾ ¾¾¾¾
¾
® Major product of the reaction is:
68.
OH
Ph
Ph
(a)
(b)
Ph
(c)
Ph
Ph
Ph
(d) None of these
Ph
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69.
Ph CH 3
Ph Et
| |
|
|
H 2SO 4
¾®
Ph — C — C — CH 3 + Ph — C — C — Et ¾ ¾¾
|
|
|
|
OH OH
OH OH
(B)
(A)
Ph O
| ||
(p) Ph — C — C — CH 3
|
CH 3
Ph O
| ||
(q) Ph — C — C — Et
|
Et
Ph O
| ||
(r) Ph — C — C — CH 3
|
Et
Ph O
| ||
(s) Ph — C — C — Et
|
CH 3
When (A) and (B) reacts with H 2 SO 4 products obtained are :
(a) p, q, r, s
70.
(b) p, q
(c) p, q, r
(d) p, q, s
Which of the following compound gives even number of Hoffmann’s exhaustive methylation
and elimination?
(a)
(b)
(c)
N
|
H
N
|
H
(d)
N
NH
CH3 I
C
71.
C
CH2
alc.KOH
CH3 CH—CH3
X = Number of chiral products
(including stereoisomer).
CH3
(a) 2
(b) 4
(c) 6
(d) 8
Cl
t-butOs
t-butO
72.
(A) ; “( A)” is :
O
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Os
t-but O
(a)
(b)
O
O t-but
Cl
(c)
(d)
O
O
Conc. H SO
2
4
¾ ¾¾¾¾
¾
® A + H 2O
73.
(Major)
OH
which of the following is product “A” in the above reaction?
(a)
(b)
(c)
(d)
74. Which of the following is true regarding increasing reactivity in the E 2 reaction with Na +
C 2H 5O - ?
CH3
CH3
CD3
CH3 — C — Br
D3C — C — Cl
CH3
(A)
(a) A is more reactive than B
(c) A is more reactive than C
H3C — C — Cl
CH3
CD3
(B)
(C)
(b) B is more reactive than A
(d) B is less reactive than C
EtO
75.
r1
Br
EtO
r2
Br
D
D
CH 2
C=
|
D
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321
Compare rate of Reactions.
(a)
r1 > r2 (b)
OH
|
76.
r1 = r2 (c)
r2 > r1 (d)
r1 =
r2
2
Å
H
Ph
Ph
+
Ph
Which statement is not true for above reaction ?
(a) It is dehydration reaction.
(b) The mechanism followed by reaction is E 1
(c) The reaction is stereo selective.
(d) The major product is Z-alkene.
ANSWERS — LEVEL 1
1.
(d)
2.
A-a
B- d
9.
(c)
10.
(d)
11.
(c)
12.
(c)
13.
(c)
14.
(d)
15.
(d)
16.
(c)
17.
(b)
18.
(b)
19.
(c)
20.
(a)
21.
(b)
22.
(a)
23.
(b)
24.
(a)
25.
(b)
26.
(a)
27.
(d)
28.
(c)
29.
(b)
30.
(c)
31.
(d)
32.
(d)
33.
(a)
34.
(a)
35.
(a)
36.
(b)
37.
(c)
38.
(c)
39.
(c)
40.
(c)
41.
(c)
42.
(b)
43.
(b)
44.
(b)
45.
(c)
46.
(a)
47.
(d)
48.
(b)
49.
(b)
50.
(a)
51.
(c)
52.
(b)
53.
(b)
54.
(b)
55.
(c)
56.
(d)
57.
(d)
58.
(b)
59.
(d)
60.
(b)
61.
(a)
62.
(b)
63.
(d)
64.
(a)
65.
(d)
66.
(b)
67.
(d)
68.
(b)
69.
(b)
70. (a,b)
71.
(b)
72.
(b)
73.
(a)
74. (a,c,d)
75.
(a)
76.
(d)
3.
(a )
4.
(c)
5.
(b)
6.
(b)
7.
(d)
8.
(b)
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Level - 2
1. Comprehension
E 2 reaction ® Elimination bimolecular
In the general mechanism of the E 2 reaction a strong base abstract a proton on a carbon
atom adjacent to the one of the leaving group. As the base abstracts a proton, a double bond
forms and the leaving group leaves.
CH3
H
CH 3ONa
+
+
CH 3 - CH 2 - CH - CH 3 ¾ ¾¾¾®
CH 3OH
|
CH3
H
(major)
Br
Mechanism :
+
dQ
+
CH3O----H
H
|
Q
CH3–— CH
CH — CH
CH3ONa + CH3 – CH – CH – CH3
|
dQ
Br
Br
anti-coplanar transition state
(staggered conformation
-lower energy)
(trans-2-butene)
A. Identify the rate of reaction of given compounds in E 2 reaction:
I
Br
F
Cl
(a)
(b)
(c)
(d)
(a) a > b > c > d
(b) a > c > b > d
(c) b > a > c > d
(d) b > d > a > c
B. In given pairs, which compound is more reactive toward E2 reaction:
CH3
CH3
Br
Br
(P)
(I)
CH3
(Q) CH3 – CH – CH3
|
Br
(III)
(II)
CH3 – CH – CD3
|
Br
(IV)
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Br
Br
(R)
(V)
(VI)
Ph — CH — CH3
|
Br (VIII)
(S) Ph — CH2— CH2 — Br
(VII )
(a) P – II, Q – III, R – VI , S – VII
(c) P – I, Q – III , R – VI , S – VII
(b) P – II , Q – III, R – VI , S – VI
(d) P – I , Q – II , R – V , S – VIII
Ph
C.
Ph
CH3
H
CH3
Br
alc.KOH
¾ ¾¾¾® ( A) ,
H
CH3
CH3
Br
alc.KOH
¾ ¾¾¾® ( B )
Ph
Ph
Product (A) and (B) are :
(a) A = cis, B = cis
(c) A = trans, B = trans
CH3
D.
CH3
NaOEt
D
(b) A = trans, B = cis
(d) A = cis, B = trans
¾ ¾¾
¾® ( A) ,
Cl
NaOEt
D
¾ ¾¾
¾® ( B )
Cl
Select the products (A) and (B) from the compounds ( P ) and (Q ) given below:
CH3
CH3
(P)
(Q)
(a) A = P, B = P
(b) A = Q, B = Q (c) A = Q, B = P
E. Which of the following compound is inert toward E2 reaction.
Br
(a) CH3 – CH – CH2 – CH3
|
Br
CH3
|
(c) CH3 — C — CH2 — Br
|
CH3
(d) A = P, B = Q
(b)
CH3
|
(d) CH3 — C — CH — CH3
|
|
CH3 Br
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2.
Match the column :
Column (I)
Column (II)
E 2 reaction
No. of possible products.
(elimination bimolecular)
Br
(a)
(p)
0
(q)
1
¾®
Br ¾ ¾¾¾
D
(r)
2
alc. KOH
D
(s)
3
alc. KOH
D
¾ ¾¾¾¾®
alc. KOH
D
¾ ¾¾¾¾®
(b)
Br
alc. KOH
(c)
Br
(d)
(including stereoisomerism)
¾ ¾¾¾¾®
3. Match the Column :
HEM = Hoffmann exhaustive methylation followed by elimination.
Column (I)
Column (II)
Reaction
Product
HEM
(a)
HEM
¾ ¾¾®
¾ ¾¾®
N
(p)
H 2C == CH — CH 2 — CH == CH 2
(q)
H 2C == CH — CH 2 — CH 2 — CH == CH 2
H
HEM
(b)
¾ ¾¾®
HEM
¾ ¾¾®
N
H
HEM
(c)
¾ ¾¾®
CH 3
HEM
¾ ¾¾®
N
(r)
|
H 2C == CH — CH 2 — C == CH 2
H
HEM
¾ ¾¾®
(d)
N
HEM
CH 3
¾ ¾¾®
(s)
|
H 2C == CH — CH — CH == CH 2
H
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4.
Match the column :
Column (I)
(a)
OH
(b)
Br
(c)
OH
(d)
5.
Hr
¾¾®
D
alc. KOH
D
¾¾¾¾®
Hr
¾¾®
D
alc. KOH
D
¾¾¾¾®
Br
Column (II)
(p)
Product are Diastereomers
(q)
Carbocation is intermediate
(r)
2nd order reaction
(s)
Ist order reaction
Match the column :
Column (I)
Cl
(a)
Cl
Column (II)
alc. KOH
¾¾¾®
(p)
Optically active product
(q)
Optically inactive product
(r)
2nd order reaction
(s)
unimolecular reaction
Cl
Cl
alc. KOH
¾¾¾®
(b)
Cl
Cl
Cl
H
(c)
aq. KOH
¾¾¾®
Cl
aq. KOH
¾¾¾®
(d)
CH3
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6. Match the column :
Column (I)
Column (II)
E 2 reactions
Number of products
(elimination bimolecular)
alc. KOH
(a)
CH 3 - CH 2 - CH 2 - CH 2 - Br ¾ ¾¾¾¾®
(b)
CH 3 - CH - CH 2 - CH 3 ¾ ¾¾¾¾®
|
Br
(including stereoisomerism)
(p)
1
(q)
2
(r)
3
(s)
4
alc. KOH
(c)
(d)
CH 3
|
alc. KOH
CH 3 - C - CH 2 - CH 3 ¾ ¾¾¾¾®
|
Br
Ph - CH 2 - CH - CH 2 - CH 3
|
Br
7. Match the column :
Column (I)
(a)
(b)
(c)
(d)
H+
D
¾¾® ( A )
OH
NaNH
D
2®
¾ ¾¾¾
Cl
O
||
EtONa
CH3 – C – CH2 – CH – CH3¾ ¾¾¾®
D
|
Br
Å
Me
N
| Me
Q
O
Column (II)
(p)
E1
(q)
E2
(r)
Ei (elimination intramolecular)
(s)
E1CB
¾¾®
D
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8. Match the column :
Column (I)
Column (II)
Reaction
Product
Å
N
(a)
Me
Me
OQ ¾¾®
D
H
(p)
D
D
Å
N
(b)
Me
Me
OQ ¾¾®
D
D
(q)
H
H
Å
N
(c)
Me
Me
OQ ¾¾®
D
(r)
H
CH3
CH3
Q
O
N
Å
(d)
Me
Me
D
CD3
9.
(s)
¾¾®
D
CD3
alc. KOH
(a)
¾ ¾¾¾® (X) products
Br
Br
alc. KOH
(b)
¾ ¾¾¾® (Y)
(c)
¾ ¾¾¾® (Z)
alc. KOH
Br
CH3
(d) CH3
H
alc. KOH
¾ ¾¾¾® (P)
CH3
Br
Sum of X + Y + Z + P =
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O
||
x NaNH2
PCl 5
10. Reaction-1 : Ph – C – CH3 ¾ ¾¾
® ¾¾ ¾ ¾®
Br
CH I
3
¾ ¾¾
® Ph – C º C – CH 3
y NaNH
¾¾ ¾ ¾2® CH – C º C – CH
3
3
Reaction-2 :
Br
z NaNH
Et -I
Reaction-3 : Ph – CH – CH2 ¾¾ ¾ ¾2® ¾ ¾¾® Ph – C º C – Et
|
|
Cl
Cl
x, y, z are moles used.
Sum of [ x + y + z = ]
11. Sum of a-hydrogen in major product of the reaction.
OH
H+
Reaction-1
¾¾
¾® ( A)
D
OH
H+
Reaction-2
¾¾
¾® ( B )
D
OH
H+
Reaction-3
¾¾
¾® (C )
D
OH
H+
Reaction-4
¾¾
¾® ( D)
D
Sum of a-hydrogen is A + B + C + D =
12. Reaction-1
Reaction-2
CH3 CH3
|
|
CH3 — C — CH — CH3
|
OH
CH3
|
CH3 – CH – CH2 – CH2 – OH
CH3
Reaction-3
CH3
CH3
|
CH – CH – CH2 – OH
Sum of a-hydrogen is (A + B + C =
H+
¾¾
¾® ( A)
D
H+
¾¾
¾® ( B )
D
H+
¾¾
¾® (C )
D
)
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OH
H+
13. Reaction-1
¾¾
¾®
( A)
D
(major)
H+
Reaction-2
¾¾
¾®
( B)
D
(major)
OH
H+
Reaction-3
¾®
OH ¾ ¾
D
(C )
(major)
Sum of a-hydrogen (A + B + C) =
14. (a)
H+
OH
OH
D
OH
(c)
H+
(b)
¾¾
¾® ( x)
H+
¾¾
¾® ( y)
H+
(d)
¾¾
¾® ( z )
D
¾¾
¾® ( p)
D
D
OH
Total number of products obtained in above reactions including minor products is (including
stereoisomer)
15.
Match the column (I) and (II).
Column (I)
Column (II)
Reaction
Type of Reaction
KSH
(a)
R -2 -chlorobutane ¾ ¾¾®
(b)
R - 2- chlorobutane ¾ ¾¾¾
¾®
(c)
2 ®
2 - bromo- 2- methyl propane ¾ ¾¾
(d)
2 ¾
4®
2- butanol ¾ ¾¾
acetone
(p)
S
(q)
S
N1
Å
EtO - Na
EtOH
HO
H SO
D
N2
(r)
E1
(s)
E2
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16.
Match the column (I) and (II).
Column (I)
Column (II)
Reaction
Type of Reaction
Cl
(a)
aq. KOH
(p)
S
(q)
S
N1
¾ ¾¾¾
¾®
Cl
(b)
alc. KOH
N2
¾ ¾¾¾
¾®
Cl
(c)
HO
(r)
E1
(s)
E2
2 ®
¾ ¾¾
OH
(d)
H+
¾¾
¾®
D
17.
Select whether the following reagent combination will result in elimination or substitution
reactions leading to the major product.
Reaction
(a)
CH 3
–
|
K Å OC(CH 3 )3
®
CH 3 — C — Cl ¾ ¾¾¾¾¾
H 2O
|
H
(b)
CH 3
|
H 2SO 4
¾®
CH 3 — C — OH ¾ ¾¾
D
|
CH 3
Substitution
Elimination
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(c)
Cl
|
alc-KOH
CH 3 — CH — CH 2 — CH 3 ¾ ¾¾¾®
(d)
CH 3
Å –
|
Na N 3
¾®
CH 3 — C — I ¾ ¾¾
|
H
Cl
(e)
-
EtO
CH3¾ ¾¾
®
D
(f)
18.
CH 3
|
HO
CH 3 — C — Cl ¾ ¾2¾®
|
CH 3
Match the Column (I) and (II) (Matrix).
Column (I)
Column (II)
Reaction
CH3
Comment on product
H+
(a)
(p)
Racemic mixture
D
(q)
Major product consist of even
number of a-hydrogen
H+
(r)
Will not undergo dehydration
¾¾
¾®
D
OH
CH3
H+
¾¾
¾®
(b)
OH
OH
(c)
¾¾
¾®
D
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(d)
H+
Major product consist of odd
number of a-hydrogen
(s)
¾¾
¾®
D
OH
19.
For each of the following amines (A through D), exhaustive methylation (treatment with
excess methyl iodide), followed by Hoffmann elimination (heating with AgOH), repeated as
necessary, removes the nitrogen atom in the form of trimethylamine. Indicate the number of
repetitive Hoffmann eliminations required to remove the nitrogen by a number (1 to 4) in
the designated answer sheet.
A.
B.
N
D.
E.
NH2
N–H
N–H
C.
N
N
F.
a.
b.
c.
d.
e.
f.
20.
¾¾® x is total number of HEM (Hoffman Exhaustive Methylation and
N
eliminations) to remove nitrogen from given compound.
alc.KOH
Br
¾ ¾¾¾® y is total number of possible E 2 product (including stereoisomer)
Sum of x+y= ?
21.
CH3
CH3—CH—CH—CH3
Br
EtOH
¾ ¾¾® (x)
( S N1 + E 1 ) products.
consider all products
( including stereoisomer)
Total number of products are :
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ANSWERS — LEVEL 2
1.
A – a; B – a; C – b; D – c; E – c;
2.
a – s; b – r; c – q; d – p
3.
a – s; b – r; c – q; d – p
4.
a – p, q, s; b – p, r; c – q, s; d – r
5.
a – p, r; b – p, r; c – p, r; d – q, r
6.
a – p; b – r; c – q; d – s
7.
a – p; b – q; c – q; d – r
8.
a – p; b – q; c – r; d – s
9.
X = 3, Y = 3, Z = 2, P = 0 Þ 3 + 3 + 2 + 0 = 8
10.
x = 3, y = 2, z = 3 Þ 3 + 2 + 3 = 8
11.
32
12.
33
13.
28
14.
x = 3 , y = 1, z = 3 , p = 2
Sum = 9
15.
(a – q), (b – s), (c – p), (d – r)
16.
(a – q), (b – s), (c – p), (d – r)
17.
Substitution –
d, f
Elimination –
a, b, c, e
18.
a – p, q; b – p, q; c – q; d – r
19.
a – 3; b – 2; c – 3; d – 1; e – 2; f – 3
20.
6
21.
6
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5C
ALKYL HALIDES
Level - 1
Br
1.
1. One eq. NaCN
¾¾¾¾¾¾® (A); Product (A) is :
2. LiAlH 4
Br
Br
Br
(a)
(b)
CH2–NH2
CH2NH2
CH2NH2
(c)
CH2–NH2
(d)
Br
Br
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2.
In the reactions given below,
(i) KCN, (ii) LiAlH 4
R – Cl ¾¾¾¾¾¾¾® Product A
(i) AgCN, (ii) LiAlH 4
R – Cl ¾¾¾¾¾¾¾® Product B
the compounds A and B are :
(a) chain isomers
(c) functional isomers
3.
(b) position isomers
(d) metamers
Which is the major product expected from the following S N 2 reaction ?
Cl
O
NaOH
¾ ¾¾
¾® Product
(a)
OH O
Cl
(b)
OH OH
OH
(c)
4.
OH O
(d)
Consider the following E 1 S N1 reaction :
Br
OH
CH3
CH3
H 2O
¾ ¾¾¾
¾®
Ethanol D
H3C H
H3C
CH3
+
H
H3 C
H
The missing product(s) is(are) :
OH
CH3
CH3
(1)
(2)
H3C
H
H
CH3
CH3
(3)
(4)
H3C
H
(a) 1, 2 and 3
(b) 3 and 4
H
(c) 2 and 3
(d) 1, 2 , 3 and 4
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5.
What is the product of the following S N 2 reaction ?
OTs O
NaBr
S 2
¾¾¾® Product
Ph
O
(a)
6.
7.
OMe
OMe
H3C
H
Br
H
O
(b)
N
OMe
H3C
H
H
Br
O
(c)
OMe
H
O
CH3
Br
(d)
H
OMe
H
CH3
H
Br
Ph
Ph
Ph
Ph
Select the reagent that will yield the greater amount of substitution on reaction with
CH 3 - CH 2 - Br :
(a) CH 3 CH 2 OK in dimethyl sulfoxide (DMSO)
(b) (CH 3 ) 3 COK in dimethyl sulfoxide (DMSO)
(c) Both (a) and (b) will give comparable amounts of substitution
(d) Neither (a) nor (b) will give any amount of substitution
Under the specified conditions, substrate X undergoes substitution and elimination reactions
to give products A - D. A and B are stereoisomers, but not enantiomers. C and D are
enantiomers. A is not an isomer of C. Which of the following could be the starting material X ?
H O
X ¾ ¾2¾® A + B + C + D
D
Br
H
(I)
(II)
(IV)
Br
H
CH3
H
(a) (I)
(b) (II)
(c) (III)
CH 3
|
CH 3 ¾ C ¾ CH 3 ,
|
Br
CH 3 ¾ CH ¾ CH 3 ,
|
Br
CH 3 ¾ CH ¾ Br
(a)
(b)
Compare rate of E 2 reaction :
(a) c > b > a
(b) a > b > c
9.
CH3
Br
(III)
H3C
H3C H
8.
CH3
Br
CH3
H3C
H
(d) (IV)
(c)
(c) b > a > c
(d) c > a > b
Which reaction results in the formation of a pair of enantiomers ?
CN –
DMSO
(a)
I
H3C
(c)
O
H ¾H
¾2¾®
I
(b)
¾ ¾¾
¾®
H
I
OH –
DMF
¾ ¾¾®
CH OH
3
¾ ¾¾
¾®
(d)
I
H
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10.
Rate limiting S N1 follows the sequence
d+ d –
R–Br
R + Br –
R + Br –
(a)
(b)
Br –
R+
(c)
True statement about sequence on the basis of assumption that R contains 3 different groups
is :
(a) more stable carbocation, greater is in the proportion of racemization
(b) the more nucleophilic the solvent greater in the proportion of inversion
(c) In above sequence (b) represent separately solvated, pair of ions
(d) All of these
11.
Compare the two methods shown for the preparation of carboxylic acids :
Mg
1. CO
diethyl ether
2. H 3O +
2
Method 1 : RBr ¾ ¾¾¾¾
¾® RMgBr ¾ ¾¾
¾
® RCO 2 H
H O, HCl
NaCN
2
Method 2 : RBr ¾ ¾¾
¾® RCN ¾ ¾¾¾
¾® RCO 2 H
heat
Which one of the following statements correctly describes this conversion ?
Br
(a)
(b)
(c)
(d)
12.
CO2H
Both method 1 and method 2 are appropriate for carrying out this conversion
Neither method 1 nor method 2 is appropriate for carrying out this conversion
Method 1 will work well, but method 2 is not appropriate
Method 2 will work well, but method 1 is not appropriate
Which of the following statements is true ?
(a) CH 3 CH 2 S - is both a stronger base and more nucleophilic than CH 3 CH 2 O (b) CH 3 CH 2 S - is a stronger base but is less nucleophilic than CH 3 CH 2 O (c) CH 3 CH 2 S - is a weaker base but is more nucleophilic than CH 3 CH 2 O (d) CH 3 CH 2 S - is both a weaker base and less nucleophilic than CH 3 CH 2 O -
13.
In the given pair of alcohols, in which pair second alcohol is more reactive than first towards
hydrogen bromide ?
CH3
H
OH
(a)
OH
and
OH
(b)
and
CH – CH3
|
OH
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(c) CH 3 - CH - CH 2 - CH 3
|
and CH 3 - CH 2 - CH - CH 2 - OH
|
OH
CH 3
(d) CH 3 - CH - CH 2 - CH 3
|
14.
and (CH 3 ) 2 C - CH 2 - CH 3
|
OH
OH
Which product would be expected to predominate in the given reaction ?
OSO2CF3
CH OH
3
¾ ¾¾
¾®
D (30°C)
OCH3
(a)
(b)
O – SO2 – CH3
(c)
15.
(d) None of these
Which is the major product of the following reaction ?
N
C
NaOH (excess)
H 2O
heat
¾ ¾¾¾¾¾® Product
CH2– Br
O
C
N
C
OH
(a)
(b)
CH2– OH
CH2– Br
O
C
(c)
H
OH
C
(d)
CH2– OH
CH2– OH
Br
CH3
16.
N
OH
D
Alc. KOH
¾® ( A) ; Major product of this reaction is :
H ¾ ¾¾¾
H
OH
(a)
D
H
CH3
(b)
D
(c)
CH3
(d)
CH3
D
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17.
Rate of S N 2 reaction is :
Br
(A)
Br
Br
(B)
(C)
(a) ( B ) > ( A) > (C )
(c) ( A) > ( B ) > (C )
18.
(b) (C ) > ( A) > ( B )
(d) ( A) > (C ) > ( B )
1-2-dichloro ethane + NaSCH 2 CH 2 SNa ¾® C 4 H 8 S 2 + ( P )
Unknown product ( P ) of the above reaction is :
S
S
(a)
(b)
S
S
(c) H - S - C = C - CH = CH - S - H
|
H
|
(d) H - C = C - CH = CH - S - H
|
H
H
|
H
Br
Moist Ag O
2
¾¾¾¾®
( A) product
19.
Major product (A) is :
OH
(a)
(b)
MeO
20.
OH
OH
OH
(c)
(d)
KCN
Cl
¾ ¾¾® Product of reaction is :
(MOM chloride)
(Methoxy methyl chloride)
(a)
Cl
CN
(b)
(c) Me - O - CH 2 - CH 2 - CN
21.
MeO
(d) O
CN
CN
CN
In the given pair of compound, in which pair the second compound is more reactive than first
toward S N 2 reaction ?
(a)
Cl or
(b)
CH2 – Cl or
Cl
Br
Br
(c)
Cl
or
(d)
or
Cl
Cl
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22.
Which compound might be synthesized by the S N 2 displacement of an alkyl-halide ?
SCH2CH3
(a)
(b)
CH2 – OH
(c) Me 3 C - OCH 3
23.
(d) All of these
Identify C in the following
series C 3 H 7 I ¾ KOH
¾¾
®
alc.
(a) (CH 3 ) 2 CH - CN
(c) Br - CH = CH - CN
24.
NBS
KCN
A ¾ ¾¾® B ¾ ¾
¾® C .
alc.
D
(b) CH 2 = CH - CH 2 CN
(d) CH 2 = CH - CH CN
|
Br
What sequence of reagents is required to accomplish the following transformation ?
OH
-
(a) (1)NBS, ROOR (2) CH 3 CH 2 O (3) 2HBr (4) NH -2 (5) disiamyl borane (6) H 2 O 2 ,OH (b) (1) Cl 2 hn (2) OH - , heat; (3) 2HCl (4) OH - , heat (5) HgSO 4 , H 2 SO 4
(c) (1) NBS, ROOR; OH - , DMSO
(d) (1) Br 2 , hn (2) t-butoxide (3) BH 3 , THF (4) H 2 O 2 , OH 25.
Which of the reagents shown below would accomplish the following transformations?
Br
26.
1. A
2. B
OH
A
(a) H 3 O +
B
BH 3 - THF; H 2 O 2 /NaOH
(b) NaOH
(c) HBr in ether
(d) NaNH 2
BH 3 - THF; H 2 O 2 /NaOH
Hg(OAc) 2 /H 2 O; NaBH 4
Hg(OAc) 2 /H 2 O; NaBH 4
What are the products obtained from the following reaction ?
Br
HC ºº CNa
¾ ¾¾¾¾® Product
Et 2O
C
C
(a)
H
C
80%
20%
C
(c)
C
80%
20%
H
(d)
100%
H
+
(b)
+
C
H
C
C
100%
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27.
The back-side attack on 2-bromobutane by methoxide (CH 3 O - ) gives the product shown
below. Which Fischer projection represents 2-bromobutane used as the reactant in this
reaction ?
OCH3
product = Et
H
Et
Et
(a) Me
(b) H
H
Br
Br
Me
Me
Me
H
(c) Br
Et
Br
(d) Me
H
Et
28.
Consider the following statements :
(1) Bridgehead halides are inert towards both S N1 and S N 2 reactions (till one of the ring size
is eight member ring)
(2) The first step in both S N1 and E 1 reactions is the same
(3) S N 2 reactions proceed with total retention of configuration
(4) E 2 eliminations are by the use of a solvent of low polarity and high concentration of a
strong base
Which of the above statements are correct?
(a) 1, 2 and 4
(b) 1 and 3
(c) 2, 3 and 4
(d) 1, 2, 3 and 4
29.
Consider the following alcohols :
CH2OH
CH2OH
O2N
(I)
CH3O
(II)
CH2OH
CH2OH
(III)
Br
(IV)
The order of decreasing reactivities of these alcohols towards substitution with HBr is :
(a) III > I > IV > II
(b) III > I > II > IV
(c) I > III > IV > II
(d) I > III > II > IV
30.
In solvolysis of 1,2-dimethyl propyl p-toluene sulfonate in acetic acid at 75°C, how many
(alkene + substitution) products will be formed ?
(a) 2
(b) 3
(c) 4
(d) 5
31.
Benzotrichloride reacts with milk of lime to form :
(a) Benzal
(b) Benzoic acid
(c) Benzyl alcohol
32.
Br - CH 2 - (CH 2 ) 2 - CH 2 - Br + CH 3 NH 2 ¾® Product of the reaction is :
(a)
(b)
N
H
33.
(d) Phenol
(c)
N
(d)
N
N
H
The configurations of the reactant and the product in the following reaction, respectively,
are:
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CO2CH3
D
(a) R, R
34.
35.
Br
CO2CH3
KCN
EtOH
H
(b) R, S
CHCN
D
(c) S, R
(d) S, S
Acetone
1-4-dichlorohexane (1 mole) + NaI (1 mole) ¾ ¾¾¾® Product of the reaction is :
(a) Cl – CH 2 – CH 2 – CH – CH 2 – CH 3
(b) I – CH 2 – CH 2 – CH – CH 2 – CH 3
|
|
I
Cl
(c) H 2 C = CH – CH – CH 2 – CH 3
(d) I – CH 2 – CH 2 – CH 2 – CH – CH 2 – CH 3
|
|
Cl
Cl
Alkyl halides can be obtained by all methods except :
2 / UV light
(b) CH 3 – CH 2 – CH 3 – CH 2 ¾Cl
(a) CH 3 CH 2 OH + HCl ZnCl 2 ¾®
¾¾¾¾
¾®
(c) C 2 H 5 OH + NaCl ¾®
(d) CH 3 COOAg + Br 2 CCl 4 ¾®
36.
In order to prepare 1-chloropropane, which of the following reactants can be employed ?
(a) Propene and HCl in the presence of peroxide
(b) Propene and Cl 2 followed by treatment with aq. KOH
(c) Propanol-1 and SOCl 2 pyridine
(d) Any of the above can be used
37.
Which alkyl halide has maximum density ?
(a) C 3 H 7 I
(b) C 2 H 5 I
(c) CH 3 I
(d) CH 3 Br
38.
Which of the following molecules would have a carbon-halogen bond most susceptible to
nucleophilic substitution ?
(a) 2-fluorobutane
(b) 2-chlorobutane (c) 2-bromobutane (d) 2-iodobutane
39.
When benzyl chloride is treated with ethanolic KCN, the major product formed is :
(a) benzyl ethyl ether (b) benzyl alcohol
(c) benzyl cyanide
(d) benzyl isocyanide
40.
Which of the following is most reactive towards nucleophilic substitution reaction ?
(a) CH 2 = CH – Cl
(b) C 6 H 5 Cl
(c) CH 3 CH = CHCl
(d)ClCH 2 – CH = CH 2
41.
Which of the following reaction will not give ether as a major product ?
(a) CH 3 CH 2 Cl + Ag 2 O(dry) ¾®
(b) (CH 3 ) 3 CCl + CH 3 CH 2 O - Na + ¾®
CH 3
|
(c) CH 3 CH 2 Cl + Na + O (d) CH 3 Cl + Na+O – – C – CH 3 ¾®
¾®
|
CH 3
(A)
+
O
H
||
Q
Q
42. O – S – O CH3 –I
(B)
Product (A) and (B) in above reaction is :
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O
O
O
||
||
||
(a) O - — S — O — H , O - — S — O — CH 3 (b) O - — S — O — H ,O -—
O
||
S — CH 3
Å|
O-
O
O
||
||
(d) O -— Å S — O , O - — S — O |
||
CH 3
H
43. Which of the following would be true for the reaction shown ?
O
O
||
||
Q Å
(c) O — S — O - CH 3 , O — S — H
|
CH3
CH3OH
Br
OCH3
(a) The rate of the reaction depends only on the alkyl bromide concentration.
(b) The rate of the reaction depends only on the methanol concentration.
(c) The rate of the reaction depends on both the alkyl halide concentration and the
methanol concentration.
(d) The rate of the reaction depends on the concentration of neither reactant.
44. The correct order of rate of S N 1 is :
Cl
Cl
Cl
(a)
(b)
<
>
Cl
H
Cl
Cl
Cl
(c)
Cl
>
<
(d)
ANSWERS — LEVEL 1
1.
(c)
2.
(c)
3.
(b )
4.
(a)
5.
(a)
6.
(a)
7.
(c)
8.
(b)
9.
(b)
10.
(d)
11.
(c)
12.
(c)
13.
(d)
14.
(a)
15.
(c)
16.
(c)
17.
(c)
18.
(a)
19.
(c)
20.
(b)
21.
(d)
22.
(d)
23.
(b)
24.
(d)
25.
(d)
26.
(b)
27.
(d)
28.
(a)
29.
(a)
30.
(d)
31.
(b)
32.
(b)
33.
(d)
34.
(d)
35.
(c)
36.
(c)
37.
(a)
38.
(d)
39.
(c)
40.
(d)
41.
(b)
42.
(b)
43.
(a)
44.
(b)
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Level - 2
1.
The following organic halide derivatives (A to J) are reacted in ethanol solution with each of
the nucleophiles : acetate, methylthiolate, cyanide and hydroxide anions. Six possible results
from these combinations of reactants are designated (1) through (6) below :
Write the number corresponding to your best estimate of the outcome of each reaction in the
appropriate answer box below.
Cl
CH2 – Cl
A
CH 3 – I
B
H
I
Possible Outcome :
(1) No reaction
(3) Elimination
(5) No reaction or slow substitution
CH3
H3C
H
B
Br
H
H3C
H
A
E
H
H
H
G
CH3
CH2 – Br
Br
Cl
(i)
H3C
Cl
D
Br
Compound
Cl
C
H
F
H3C
J
(2) Substitution
(4) Substitution and elimination
(6) No reaction or slow elimination
C
D
E
F
G
H
I
J
CH 3 CO 2Na
(ii) CH 3 SNa
(iii) NaCN
(iv) NaOH
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2.
In each of the following sections three organic halogen compounds are listed. In the box
given enter a number (1 to 3) indicating the order of reactivity of the designated (1 is most
reactive and 3 is least).
(a) S N 2 substitution by NaOCOCH 3 in methanol:
1. CH 3CH 2CH 2Br £
2. (CH 3 ) 2 CHBr £
3. CH 2 = CHCH 2Br £
(b) S N 2 substitution by NaI in acetone:
1. C 6 H 5Cl
2. C 6 H 5CH 2Cl £
3. C 6 H 5CHClCH 3 £
£
(c) S N 2 substitution by NaCN in methanol:
1. CH 3CH 2Cl
2. CH 3CH 2F
3. CH 3CH 2I
£
£
£
(d) S N 2 substitution by NaSCH 3 in methanol:
1. (CH 3 ) 2 CHCH 2CH 2Br£ 2. CH 3CH 2CHBrCH 2CH 3£ 3. (CH 3 ) 3 CCH 2Br £
3.
Isobutyl alcohol (2-methyl-1-propanol), (CH 3 ) 2 CHCH 2OH, can be transformed to each of
the compounds (a through l) listed in the left-hand column. In each case the number of steps
needed to accomplish the change is noted, and an answer box is provided for your reagent
selections. Fourteen reagents (designated A through N) are listed in the right-hand column.
Write letters designating the reagent or reagents you believe will achieve the desired
transformation in the box to the right of the product formula. In the case of a multi-step
sequence write the reagents in the order they are to be used. In some cases you may wish to
use a previously prepared compound as a reactant. If so, write the number (a to l)
corresponding to the desired compound.
Desired product
No. of
Write
Steps
Options
Reagent List
a. (CH 3 ) 2 CHCH 2Br
one
A. Hg(OAc) 2 in H 2O
b. (CH 3 ) 2 C = CH 2
one
B. PBr 3 & heat
c. (CH 3 ) 2 CHCH = O
one
C. NaBH 4 in alcohol
d. (CH 3 ) 2 CHCO 2H
one
D. LiAlH 4 in THF (aqueous workup)
e. (CH 3 ) 3 CBr
two
E. NaCN in alcohol
f. (CH 3 ) 2 CHCH 2C º N
two
F. PCC in CH 2Cl 2
g. (CH 3 ) 2 CHCH 2OCOCH 3
one
G. Jones' reagent (CrO 3 in H 3O + )
h. (CH 3 ) 2 CHCO 2C 2H 5
two
H. HBr in CH 2Cl 2
i. (CH 3 ) 2 CHCH 2OCH 2(CH 3 )
two
I.
H 3PO 4 and heat
j. (CH 3 ) 3 COH
three
J. (CH 3CO) 2 O + pyridine
k. (CH 3 ) 2 CHCH 2NH 2
three
K. NaN 3 in aqueous alcohol
l. (CH 3 ) 2 CHCH 2CH 2NH 2
two
L. C 6 H 5CO 3 H in CH 2Cl 2 (peracid)
M. NaH in ether and heat
N. C 2H 5OH + acid catalyst & heat
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Subjective Problems
CH3
1.
CH3OH
?
Br
X = Total number of substitution and elimination product(s). Find the value of X.
ANSWERS — LEVEL 2
1.
A
B
C
D
E
F
G
H
I
J
(i)
2
2
2
1
1
1
6
2
2
6
(ii)
2
2
2
1
1
5
6
2
2
6
(iii)
2
2
2
1
1
1
3
3
2
3
(iv)
4
2
2
1
1
5
3
3
4
3
2.
a – 3 > 1 > 2;
b – 2 > 3 > 1;
c – 3 > 1 > 2;
d–1>2>3
3.
a – B; b – I; c – F; d – G; e – I, H or 2 H; f – B, E or 1, E; g – J; h – G, N or 4N
i – N, j – I, A, C or 2AC or ILD or 2LD; k – B, K, D or 1KD; l – B, E, D or 1ED or 6D
Subjective Problems
1. 4
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6
ALCOHOL, ETHERS AND EPOXIDES
Level - 1
1.
The following transformation involves a carbocation rearrangement. The carbocation is
generated by protonation of the hydroxyl group, followed by the loss of water. Which bond
has to migrate in the carbocation to yield the product indicated (after the deprotonation) ?
OH
H2SO4
(b)
(c)
H
(d)
(a)
(a) a
2.
(b) b
(c) c
(d) d
Identify the major product.
HO
H SO
4
¾ ¾2 ¾
¾
® Product
(a)
(b)
(c)
(d)
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CH2 – OH
Et
3.
O
||
CH2 – C– Cl
(A) (major)
N
|
H
O
||
CH2 – O – C – CH3
CH2 – OH
Et
(a)
Et
(b)
N
|
H
N
|
C – CH3
||
O
O
||
C – CH3
CH2
Et
(c)
4.
(d)
N
N
|
|
H
H
Predict the product when given compound reacts with LiAlH 4 :
O
O
||
||
C
C
OCH3
H
||
O
(A)
O
||
C – O – CH3
OH
(a)
O
||
C – O – CH 3
OH
(b)
||
O
OH
O
||
C
OH
OH
(c)
(d)
H
OH
OH
OH
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5.
Predict the product when given compound (A, in the above question 4) reacts with NaBH 4 .
O
O
||
||
OH
OH
C – O – CH3
C – O – CH 3
(a)
(b)
||
O
OH
O
||
C
OH
OH
(c)
H
(d)
OH
O
OH
OH
O
C–O–H
+ CH 3 – O
6.
18
C – O – CH 3
HCl
–H
The labelled –O 18 will be in :
(a) H 2O
(c) Both (a) and (b)
+ H 2O
Catalyst
Methyl benzoate
(b) Methyl benzoate
(d) Benzoic acid
18
7.
CO 2H
CH 2 – OH
H+
|
+ |
¾¾® (A); Product (A) is :
18
D
CH 2 – OH
CO 2H
O
|| 18
C – O – CH 2
|
(b) |
C – O – CH 2
|| 18
O
O
||
C – O – CH 2
|
(a) |
C – O – CH 2
||
O
18
8.
O
||
C – O – CH 2
|
(c) |
C – O – CH 2
||
18
O
Which is oxidized most easily ?
O O
|| ||
(d) H – O – C – C – O – CH 2 – CH 2 – OH
(a) CH 3 – CHOH – CH 3
(b)
OH
(c) CH 3 – CH 2 – O – CH 2 – CH 3
(d)
CH3
OH
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OH
CO2H
9.
K Cr O
2 2 7
¾¾
¾¾® ( P ); Product (P) is :
D
O
O
CO2H
CO2H
(a)
10.
(b)
(c)
(d)
Which of the following react with HBr at faster rate ?
OH
(a)
(b)
OH
CH3
OH
(c)
O
||
C – OH
O
11.
(d)
OH
CH3
CH3 – C
CH3
OH
|
¾¾® CH3 – CH
Above conversion can be done by :
(a) NaBH 4
(b) LiAlH 4
CH2 – OH
(c) PCC
(d) KMnO 4
CO2H
2 CH OH
3
¾ ¾ ¾¾
® (A) ; Product (A) is :
12.
H 2SO 4 , D
O
||
C – CH3
CO2H
CO2CH3
CO2CH3
CO2CH3
(a)
(b)
(c)
(d)
CO2CH3
CO2H
5
13.
OH
4
6
1
3
(a)
(c)
2
O
1||
5
OH
6
Ph
H SO
4
¾ ¾2 ¾
¾
® ( P ) ; Unknown (P) of the reaction is :
Ph
Ph
2
5
3
O
||
6 1
2
3
Ph
99% yield
4
4
C – CH3
||
O
CO2CH3
(b)
6
1 C
5
4
3
Ph
2
5
Ph
Ph
Ph
(d) 4
3
OH
1
C
6
Ph
Ph
2
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351
14.
Predict the major product of the given reaction.
OH
+
¾ H¾
¾® (A); Product (A) is :
OH
OMe
OMe
(a)
OMe
(b)
O
(c)
(d)
MeO
15.
OMe
O
O
Identify the major product,
OH
H+
Product
O
OH
O
(a)
O
(b)
(c)
O
O
(d)
O
O
O
O
O
+
¾ H¾
¾® (A); Product (A) is :
16.
O
O
O
O
(a)
(b)
O
O
(d) O
(c)
O
OCH3 OCH
3
4
¾ LiAlH
¾¾
¾
® (A) Major; product (A) is :
17.
CO2CH3
OH
(a)
(b)
CH2OH
OH
O
OCH3
OCH3
(c)
OH
OCH3
(d)
OH
CH2OH
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OH
I 2 + NaOH
¾ ¾ ¾¾® CHI 3 + ( A); Compound (A) is :
18.
(Iodoform)
OH
(Resorcinol)
O
O
O
||
||
(b) H – O – C – (CH 2 ) 2 – C – OH
ONa
(a)
CO2Na
CH2
O
||
(c) CH 3 – CH 2 – CH 2 – CH 2 – C – OH
O
||
(d) CH 3 – (CH 2 ) 3 – C – ONa
OH
H CrO
4
¾ ¾2 ¾¾
® (A). Product (A) is :
19.
(3º alcohol)
OH
(a) No reaction
(b)
(c)
(d)
O
CO2H
O
- Li(excess)
I2
¾(1)CH
¾ ¾3 ¾
¾
¾
¾®( A) ¾¾
®( B ) + CHI 3 ¯; Compound (B) is :
Å
20.
NaOH
(2) H
O
O
– +
O Na
(a)
(b)
– +
O Na
CO2Na
(c)
CO2Na
(d)
OH
18
- Br
¾ H¾¾
® Major product obtained in the reaction is :
CCl
OH
21.
4
18
O
(a)
O
(b)
Br
(c)
OH
Br
(d)
OH
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22.
Consider the following alcohols,
CH2OH
CH2OH
(I)
(II)
O2N
CH2OH
(III)
CH2OH
(IV)
CH3O
Br
The order of decreasing reactivities of these alcohols towards nucleophilic substitution with
HBr is:
(a) III > I > IV > II
(b) III > I > II > IV
(c) I > III > IV > II
(d) I > III > II > IV
O
23.
O
O
NaBH
4
¾¾¾®
(P)
O
O
O
O
LiAlH
4
¾¾¾®
(Q)
Sum of number of alcoholic groups in product ( P ) and (Q ) is:
(a) 1
(b) 2
(c) 3
24.
(d) 5
In presence of dil. HCl, compound A is converted to a constitutional isomer (B), compound B
is:
O
||
HO
(a) NH2
O
||
O–C
NH – C
NO2
NO2
(b) NH2
O
OH
(c) NH2
O–C
H
OH
|
O–C
|
H
NO2
NO2
O
C
(d)
NH2
Ar
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N
CH3
25.
|
CH3
OH
CrO3ClQ
H
(A) (ten carbon atom)
dichloro methane
CH3
(a)
(b)
(c)
(d)
O
OH
CO2Et
26.
O
CH2OH
; Product of the reaction is:
LiAlH4
(a) Racemic
(c) Meso
OH
27.
O
(b) Diastereomer
(d) Optically pure
(1) EtLi (3.5 eq)
CO2H
(2) H +, H 2O
( A) ; Chemist added extra 0.5 mole of Et-Li
65% yield
in above reaction to obtain product (A), which is?
O
O
||
||
Et
(a)
(b)
O
||
(c)
28.
O
||
C – Et
O
||
Et
CH2OH
OH
(d)
Et
O
+ Ph – C – O – H
HO
HCl
Major product of above esterification reaction is:
O
CH2 – O – C – Ph
O
||
(a)
Ph
OH
(b)
HO
O
O
||
O – C – Ph
CH2 – O – Ph
(c)
(d)
HO
HO
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14
C label
OTs
29.
OCOR
OCOR
RCO 2 H
¾¾¾® ;
+
no label
(c) SN — NGP
(b) S N 2
(a) S N1
HO
(d) SN — Ar
Ac 2O
30.
(A); Product (A) of reaction is :
¾¾¾¾®
100 °C
NH2
O
O
||
O
||
O
O
(a)
OH
(b)
O
(c)
(d)
NH
NH2
NH
NH
O
OH
Q
N
CrO3Cl , (PCC).CH2Cl2
H
31.
||
O
||
O
Product of the reaction is :
CH3 – C – OH
CH3
CHO
OH
(a)
CO2H
(b)
(c)
OH
32.
O
(d)
OH
OH
Which is the best reagent to convert isopropyl alcohol to isopropyl bromide ?
CH3
CH3
CH3 – CH – OH
(a) HBr
(b) SOBr 2
?
CH3 – CH – Br
(c) Br 2
(d) CH 3MgBr
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NH2
Ph
OH
33.
HNO2
A
CH3
H
Ph
Major product obtained in the above reaction is :
O
(a)
O
H CH 3
Ph — C
(b)
CH3 H
Ph — C
Ph
Ph
(c) Racemic
(d) Diastereomers
HIO4
(1) LiAlH 4 (excess)
OH ¾¾®
(B)
(A) ¾¾¾¾¾¾®
(2) H +
OH
34.
Total number of stereoisomers of product ( B ) will be:
(a) 2
(b) 3
(c) 4
O
S – C – CH 3
1. HO–
2. H+
35.
(d) 5
Major product of the reaction is :
O – C – CH 3
O
SH
(a)
SH
(b)
(c)
S
(d)
O
(c)
S
(d)
O
OH
OH
O
S – C – CH3
HOQ
36.
O – C – CH3
O
SH
(a)
SH
(b)
OH
OH
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CH3
O
37.
CH 3MgBr H+
OH
O
KMnO 4 (cold dil.)
H+ D
CrO 3
(1)
(2)
(3)
For the above conversion the correct order of reagents used is :
(a) 1 ® 2 ® 3 ® 4
(b) 1 ® 4 ® 3 ® 2
(c) 1 ® 4 ® 2 ® 3
(d) 2 ® 3 ® 4 ® 1
CH3
38.
CH3
CH3
CH3
C – CH2 – CH3
|
OH
(x)
C — C H – CH3
CH3
O
(y)
CH – C H – CH3
CH3
OH
(2º alcohol)
(3º alcohol)
Find missing reagents.
(a) x = LiAlH 4 , y = NaBH 4
(c) x = LiAlH 4 , y = LiAlH 4 AlCl 3
39.
(4)
(b) x = LiAlH 4 AlCl 3 , y = LiAlH 4
(d) x = H 2 Ni , y = H 2 Pt
In solvolysis of 1, 2-dimethyl propyl p-toluene sulfonate in acetic acid at 75ºC, (alkene +
substitution products) will be formed by mechanism ?
(d) S N1 , E 1
(c) S N1 , E 2
(b) S N 2 , E 1
(a) S N 2 , E 2
O
O
40.
¾¾¾®
O
LiAlH
4
¾¾¾®
(A)
xAc2O
(B)
x = moles of anhydride consumed
(a) 1
(b) 2
41.
(c) 3
(d) 4
Identify product when (R) – and (S) – 2 – butanol reacts with (R,R) tartaric acid in acidic
medium.
(a) Racemic
(b) Diastereomer
(c) Meso
(d) Pure enantiomer
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42.
43.
An alcohol of formula C 9 H 12O reacts with Na 2Cr 2O 7 to form a compound having formula
C 9 H 10 O. The original alcohol might be :
OH
|
CH2 – CH2 – CH2 – OH
CH – CH2 – CH3
(a)
(b)
CH3
CH3
|
|
C – OH
CH – CH2OH
(c)
(d)
|
CH3
An optically active alcohol of formula C 9 H 12O 2 produced the following compound when
refluxed with KMnO 4 .
O
O
HO –– C
C –– OH
The original compound showed these properties also :
Na
C9H12O2
(A)
Br2
CrO3/H+
cool
What is structure of (A)?
CH3
(a)
44.
H2 liberated
no rapid reaction
C9H8O3
OH
OH
OH
OH
(b)
(c)
CH3
OH
Which are not cleaved by HIO 4 ?
I : glycerol
III : 1, 3-propenediol
(a) I, II, III, IV
(c) II, III
(d) both (a) and (b)
CH3
II : glycol
IV : methoxy-2-propanol
(b) I, II
(d) III, IV
45.
Which of the following reactions require an oxidising agent ?
(a) CH 3 — CH == CH 2 ¾® CH 3 — CH 2 — CH 3
(b) CH 3 — CH 2OH ¾® CH 3CHO
(c) CH 3 — CH 2Cl ¾® CH 3 — CH 3
(d) CH 3 — CH 2OH ¾® CH 3 — CH 2Cl
46.
What is the major product of the following reaction ?
O
NaBH4
product
CO2H
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OH
OH
(a)
OH
O
(b)
(c)
(d)
CO2H
CO2H
CO2CH3
CH2OH
47.
Which of the esters shown, after reduction with LiAlH4 and aqueous workup, will yield two
molecules of only a single alcohol ?
(a) CH 3CH 2CO 2CH 2CH 3
(b) C 6 H 5CO 2CH 2C 6 H 5
(c) C 6 H 5CO 2C 6 H 5
(d) None of these
48.
For the following reaction, select the statement that best describes the change.
RCH 2OH + PCC [C 5H 5NH + ClCrO -3 ] ¾¾®
(a)
(b)
(c)
(d)
49.
The alcohol is oxidized to an acid, and the Cr(VI) is reduced
The alcohol is oxidized to an aldehyde, and the Cr(VI) is reduced
The alcohol is reduced to an aldehyde, and the Cr(III) is oxidized
The alcohol is oxidized to a ketone, and the Cr(VI) is reduced
What is the product of the following reaction ?
CH3
CH3
H3C
C == C
H
H
OsO4(cat.), (CH3)3CCOOH
(CH3)3COH,HO–
H
OH
H
OH
HO
OH
H
HO
H
H
OH
CH3
CH3
CH3
3
2
1
(b) 1 : 1 mixture of 2 and 3
(d) 1 : 1 : 1 mixture of 1, 2, and 3
(a) Only 1
(c) Only 2
50.
CH3
CH3
H
An organic compound B is formed by the reaction of ethylmagnesium iodide (CH3CH2MgI)
with a substance A, followed by treatment with dilute aqueous acid. Compound B does not
react with PCC in dichloromethane. Identify A ?
O
O
O
||
||
(a) CH — C — H
(b) CH CH C CH
(c) H C == O
(d) H2C – CH2
3
3
2
3
2
51.
Which of the following reagents would carry out the following transformation ? (D = 2H)
OH
O
|
?
CCH3
CCH3
|
D
(a) NaBD 4 in CH 3OH
(b) LiAlH 4 , then D 2O
(c) NaBD 4 in CH 3OD
(d) LiAlD 4 , then D 2O
52.
Which sequence of steps describes the best synthesis of 2-methyl-3-pentanone ?
O
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(a) (1) 1-Propanol + (CH 3 ) 2 CHMgBr, diethyl ether
(2) H 3O +
(3)
(b) (1)
(2)
(3)
(c) (1)
(2)
(3)
PCC, CH 2Cl 2
1-Propanol + Na 2Cr 2O 7 , H 2SO 4 , H 2O, heat
SOCl 2
(CH 3 ) 2 CHCl, AlCl 3
1-Propanol + PCC, CH 2Cl 2
(CH 3 ) 2 CHLi, diethyl ether
H 3O +
(4)
(d) (1)
(2)
(3)
Na 2Cr 2O 7 ,H 2SO 4 ,H 2O, heat
2-Propanol + Na 2Cr 2O 7 , H 2SO 4 , H 2O, heat
CH 3CH 2CH 2Li, diethyl ether
H 3O +
(4) PCC, CH 2Cl 2
53.
Diols (I-IV) which react with CrO 3 in aqueous H 2SO 4 and yield products that readily under
go dercarboxylation on heating, are :
OH
OH
(I) HO
(II) HO
OH
(III) HO
(IV)
OH
OH
(a) I and II
54.
(b) II and III
(c) II and IV
(d) I and IV
Which of following compounds are not oxidized by HIO 4 ?
CH 3 — CH — OH
CH 3 — C == O
(1)
(2)
|
|
CH 2 — OH
H — C == O
(3)
CH 3 — C == O
|
CH 3 — C == O
O
(5)
(a) 5, 6, 7
(4)
CH 3 — C == O
|
CH 3 — CH — NH 2
CH 2 — OCH 3
(6) |
CH 2 — OH
O
||
(7) C — OH
|
CH 2 — OH
(b) 4, 5, 6, 7
(c) 6, 7
(d) 3, 4, 5, 6, 7
CH2OH
55.
TsCl
( A) ¾¾¾¾¾® ( B ) 84%; Final product (B) will be :
OH ¾¾¾¾®
Pyridine
80 °C
0 °C
(HMPT Solvent)
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O
O
(a)
56.
(b)
O
(c)
Unknown (A) in the reaction (given in Q. 55) is :
CH2 – OTs
OH
(a)
(b)
CH2 – CH3
57.
CH2OH
OTs
(d)
In the given table, identify the incorrect option. The digit in box indicate the moles of that
substance.
HIO 4
consumed
Reactant
58.
(d)
O
OH
(c)
O
HCO 2H
formed
HCHO
formed
(a)
OH
|
HO – CH 2 – CH – CH 2 – OH
2
1
2
(b)
OH OH OH
|
|
|
R – CH – CH – CH – CH 2 – OH
3
2
1
(c)
OCH 3
|
HO – CH 2 – CH – CH 2OH
0
0
0
(d)
OH OCH 3
|
|
HO – CH 2 – CH – CH 2
1
1
1
3
2
Succinic acid ¾¾®( A) ¾ NH
¾¾
®( B ) ¾ Br
¾
¾
®(C ); Product (C) will be :
D
D
KOH
CH 2 – CO 2H
CH 2 – CO 2H
(a) |
(b) |
CH 2 – CH 2 – NH 2
CH 2 – NH 2
CH 2 – CO -2 K +
(c) |
CH 2 – NH 2
CH 2 – CO 2H
(d) |
CH 2 – CH 2 – Br
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59A.
Given are the structures of cyclic D-glucoside. Moles of HIO 4 consumed with X and Y are
......... respectively:
CHOR
RO
CH
OH
O
HO
O
OH
OH
OH
OH
CH2 – OH
CH2 – OH
(X)
(Y)
(a) 2, 2
(c) 2, 3
(b) 3, 3
(d) 3, 2
B.
Moles of formic acid formed in X and Y respectively are:
(a) 1, 2
(b) 2, 1
(c) 2, 3
(d) 3, 2
C.
Moles of HCHO formed are:
(a) 1, 1
(c) 1, 2
(b) 2, 2
(d) 2, 1
60.
In which of the following group, each member gives positive iodoform test ?
(a) methanol, ethanol, propanone
(b) ethanol, isopropanal, methanal
(c) ethanol, ethanal, isopropyl alcohol
(d) propanal, propanol-2, propanone
61.
H 2O 18 + Na ¾® ( A) + ( B )
(base)
O
||
CH 3 – C – O – CH 2 – CH 3 + ( A) ¾® (C ) + ( D) alcohol
Product (C) of the reactions is:
O
||
(a) CH 3 – C – O– H
O
||
(b) CH 3 – C – O – H
O
|| 18
(c) CH 3 — C — O –
O
||
Å
(d) CH 3 – C – O Q N a
18
18
O
O
62A.
H2
0.1 M NaOH
(Ph 3 P)3 RhCl
H 2O
(Methanol)
¾¾¾¾¾® ( A) ¾¾¾¾¾® ( B ) +
NO2
O
Product (B) of the reaction is :
(C )
(Contains no nitrogen)
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Q
CO2
OH
(a)
(b)
NO2
NO2
O
O
C – O – CH3
C–O
(c)
(d)
NO2
B.
Product (C) of above reaction is :
OH
HO
(a)
63.
O
NO2
HO
(b)
(c)
OH
(d)
O
O
O
O
Two unknown compounds X and Y, both having molecular formula C 4 H 8 O, give following
results with four chemical tests.
Bromine
Na metal
Chromic acid
Lucas reagent
Compound X
decolourises
bubbles
Orange to Green
No reaction
Compound Y
No reaction
No reaction
No reaction
No reaction
Compound X and Y respectively are :
O
||
(a) CH 3 – CH 2 – C – CH 3 ;
(c)
64.
OH
;
O
OH ;
(b)
O
OO
||
(d) CH 3 – CH 2 – CH 2 – C – H ;
O
O
H 3O +
CH 3 Br
LiH
L ¾¾¾® M ¾¾¾® N + CH 3OH
COH ¾¾¾¾¾¾®
dimethoxy ethane
Product (N) is :
O
(a)
CH3
(c)
O
||
C—O—H
(b)
C – CH3
(d)
OH
|
CH – CH3
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65.
Assign the structure of major product (X) of the reaction given below.
O
CH – COH
|
OH
O
||
CH – C – OH
|
OEt
O
(a)
(c)
CH – C – Cl
|
OEt
Cl
O
CH3CH2OH
SOCl2
HCl(g), D
D
O
||
CH – C – OEt
|
Cl
(b)
O
CH = CH – C – O – Et
(d)
O
||
CH — C — OCH2 — CH3 + CH3 – COH
66.
acetic acid
(7 mole)
ethyl-2-chloro
2-phenyl acetate
(1 mole)
(X)
(A)
HCl
D, 1.5 h
+ (B)
(contains chlorine)
Product (A) and (B) respectively in the above reaction are :
O
O
(a)
(b)
(c)
(d)
67.
CH – C – OH, CH 3 – C – OCH 2CH3
|
Cl
O
O
||
||
CH – C – OEt, CH3 – C – OCH3
|
Cl
O
O
||
||
CH – C – OEt, CH3 – C – OH
|
Cl
O
||
CH2 – Cl, CH3 – C – OH
O
||
H 2C = CH – C – OCH 3 + CH 3CH 2CH 2OH ¾¾¾® ( A) + CH 3OH
methylacrylate
bpt 81 °C
n - butyl alcohol
bpt 117 °C
Product (A) of above reaction is :
O
||
(a) H 2C == CH – C – OCH 2CH 2CH 3
O
||
(c) H 2 C – CH 2 C – OCH 3
|
OCH 3
TsOH, D
bpt,145°C
bpt 65°C
O
||
(b) H 2C == CH – C – O – CH(Me) 2
O
||
(d) H 3C – (CH 2 ) 4 – C – O – CH 3
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68.
69.
OH
3Ac 2O ¾®
OH
(acetic anhydride)
OH
In above reaction molecular formula of glycerol increases by :
(a) C 4 H 4 O 2
(b) C 6 H 6 O 6
(c) C 6 H 6 O 2
(d) C 6 H 6 O 3
Give the best conditions for this transformation:
OCH3
H3C
70.
H3C
O
OCH3
(a) CH 3OH,H + (cat.),heat
(b) H 2O,H + (cat.),heat
(c) Mg,ether,CH 3OH
(d) SOCl 2 ,CH 3OH
Give the major organic product of the following reaction.
O
(1) sodium acetylide
¾¾¾¾¾¾¾¾¾¾®
Product
+
(2) H 2O,H to neutralize
O
OH
(a)
(b)
HO
(c)
(d)
OH
OH
PCC
71.
(A)
OH
OH
H+
(B)
(1) MeMgBr
(2) H3OÅ
(C)
NaBH4, EtOH
(D)
Product (D) in above reaction is :
OH
OH
OH
(a)
(b)
OH OH
OH
(c)
OH
OH
(d)
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72.
Select the best method for the preparation of the following compounds :
OH
OH
and
CH3
(a)
(b)
(c)
(d)
73.
CH3
(MCPBA = Metachloro per benzoic acid )
reaction of cyclohexanone with CH 3Li
reaction of 1-methylcyclohexene with Hg(OAc) 2 followed by NaBH 4
reaction of cyclohexene with BH 3 ;NaOH H 2O 2 , following by CH 3Br
reaction of cyclohexene with MCPBA, followed by CH 3MgBr
Identify the reagents (1-4), required for the transformations shown and arrange them in
correct order.
Ph
Ph
Ph
1
Ph
Ph
Ph
H+
H
O
Ph
H
HOH2C
O
OH
HO
H
Ph
4
Ph
74.
O O
Ph
3
O
OH OH
Ph
Ph
2
O
O
(1)
(3)
(a)
(c)
CH2OH
O
LAH (LiAlH 4 )
NaIO 4
1®3®4®2
2®1®3®4
(2)
(4)
(b)
(d)
OsO 4
NaBH 4
2®3®1®4
1®2®3®4
Which describes the best stereochemical aspects of the following reaction ?
CH3
Ph
(a)
(b)
(c)
(d)
75.
CD3
OH
Br
¾ H–
¾¾
® Product
Inversion of configuration occurs at the carbon undergoing substitution.
Retention of configuration occurs at the carbon undergoing substitution.
Racemization (loss of configuration) occurs at the carbon undergoing substitution.
The carbon undergoing substitution is not stereogenic
Which of following is an example of Pinacol-Diazotization ?
O
O
|
|
|
|
+
2
(a) Me 2C – CMe 2 ¾ Ag
¾¾
¾
® Me – C – CMe 3
¾
¾® Me – C – CMe 3 (b) Me 2C – CMe 2 ¾ NaNO
HCl
| |
| |
NH
Br
OH
OH
2
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O
|
|
Å
(c) Me 2C – CMe 2 ¾ H
¾
¾® Me – C – CMe 3
| |
OH OH
76.
OH
O
H+
(d)
R
R
R
R
Å
3O
¾¾
® B + C ; (B) and (C) both give +ve iodoform test. Compound (A) is :
( A) ¾ H
C 5 H10O
(a) CH 3 – CH = CH – O – CH 2 – CH 3
77.
H
|
(b) CH 3 - C - O - CH 2 - CH 3
|
CH 3
(c) CH 3 – C – O – CH 2 – CH 3
(d) both (b) and (c)
||
CH 2
A solution of Ph 3CCO 2H in conc. H 2SO 4 gives (X) when poured into methanol X is :
O
O
||
||
(b) Ph 2CH – C – O – CH 3
(a) Ph 3C – C – O – CH 3
(c) Ph 3C – OCH 3
(d) Ph 3C – CH 3
OH
LiAlH
TsCl
4
¾ Pyridine
¾¾¾® ( A) ¾ ¾¾
¾
® ( B)
78.
Product (B) of the above reaction is :
Cl
(a)
79.
(b)
(c)
(d)
In the given pair of alcohol, in which pair second alcohol is more reactive than first towards
hydrogen bromide?
CH3
(a)
OH
H
and
OH
OH
and
(b)
CH – CH3
|
OH
(c) CH 3 — CH — CH 2 — CH 3 and CH 3 — CH 2 — CH — CH 2 — OH
|
|
OH
CH 3
(d) CH 3 — CH — CH 2 — CH 3 and (CH 3 ) 2 C — CH 2 — CH 3
|
|
OH
OH
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80.
Rank the transition states that occur during the following reaction steps in order of
increasing stability (least ® most stable)
+
1. H 3C — OH 2 ¾® CH +3 + H 2O
+
2. (CH 3 ) 3 C — OH 2 ¾® (CH 3 ) 3 C + + H 2O
+
3. (CH 3 ) 2 CH — OH 2 ¾® (CH 3 ) 2 CH + + H 2O
(a) 1 < 2 < 3
(b) 2 < 3 < 1
(c) 1 < 3 < 2
81.
OH
HO
MnO
¾ ¾¾2 ® (A), Product (A) is :
OH
(a) O == C
|
H
82.
CHO
(b) HO
CH2 O
(c) HO
(d) 2 < 1 < 3
O
(d) HO
C—H
C—O—H
In which of the following reactions hydrogen gas will not be evolved ?
K
(b) CH 3 — CH 2 — OH ¾¾
(a) CH 3 — CH 2 — OH ¾ Na
®
¾®
CH MgBr
Al
(c) CH 3 — CH — OH ¾¾
®
3
(d) CH 3 — CH — OH ¾ ¾¾¾
®
|
CH 3
|
CH 3
PBr3
(A)
83.
Mg, ether
(C)
Na2Cr2O7
Grignard reagent
(D)
(B)
H2SO4
H3O
(3, 4-dimethyl
3-hexanol)
When Grignard reagent reacts with (B) product (D) will obtained.
Reactant (A) of the above reaction is :
(a)
(b)
OH
(c)
OH
84.
(d)
OH
OH
LiAlH 4
( A) ¾¾¾®
; structure of (A) is :
2( B )
(Chiral alcohol only)
O
||
(a) CH 3 ¾ CH ¾ C ¾ O ¾ CH ¾ CH 3
|
|
Et
Et
O
O
(c)
O
O
||
(b) CH 3 ¾ CH ¾ C ¾ O ¾ CH 2 ¾ CH ¾ CH 3
|
|
Et
Et
(d)
OH
O
¾¾¾®
85.
NO2
NO2
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Above conversion can be acheived by :
(a) LiAlH 4
(b) NaBH 4
(c) H 2 / Ni
(d) CrO 3
OH O
|
||
CH–COH
86.
+ EtOH ¾ HCl
¾
¾® (86%)
(Mandelicacid)
Identify product of above Fischer esterification reaction :
O - Et
O
|
(a) Ph - CH - CO 2H
(b) Ph – CH – C = O
O
(c) Ph - CH - CO 2Et
(d) Ph - CH - C - Et
||
|
|
OH
OH
O
CH2CH2COH
CH3
H OÅ
CH Li
CH Li
3
3
3
¾ ¾¾
®( A) ¾ ¾¾
® ( B ) ¾ ¾¾
® (C )
87.
O
O
Product (C) of the above reaction is :
O
OH
||
OH
|
(a) CH 3 - C - CH 2 -CH 2 - C - CH 3
|
O
||
|
(b) CH 3 - C - CH 2 - CH 2 - C - CH 3
CH 3
|
|
CH 3
CH 3
O
O
||
||
(c) CH 3 - C - CH 2 - CH 2 - C - CH 3
88.
OH
|
O
||
(d) CH 3 - C - CH 2 - C - CH 3
What is the major product of the following reaction ?
OH
|
CrO
3
CH 3 - CH - CH 2 - CH 2 - OH ¾ Pyridine
¾¾¾¾
® Product
cold
OH
O
|
O
||
||
(a) CH 3 - CH - CH 2 - C - H
O
||
O
|
(c) CH 3 - C - CH 2 - C - OH
||
(b) CH 3 - C - CH 2 - C - H
OH
||
O
O
||
(d) CH 3 - CH - CH 2 - C - OH
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89.
The major reason that phenol is a better Bronsted acid than cyclohexanol is that :
(a) it is a better proton donor.
(b) the cyclohexyl group is an electron donating group by induction, which destabilizes the
anion formed in the reaction by resonance.
(c) phenol is able to stabilize the anion formed in the reaction.
(d) the phenyl group is an electron withdrawing group by induction, which stabilizes the
anion formed in the reaction.
90.
Which of these reagents would accomplish the following reduction ?
O
OH
||
|
N º C - CH 2 - C - CH 2 - CH = CH 2 ¾® N º C - CH 2 - C - CH 2 - CH = CH 2
H
(a) NaBH 4
(c) 1 mole H 2 , poisoned catalyst, low pressure
(b) LiAlH 4
(d) H3O+
CH – CH2 – OH
||
CH – CO2Et
||
MnO
A)
¾(¾
¾
®
91.
¾ ¾¾2 ® (B)
Identify A and B :
CH – CO2H
CH – CHO
(a) A = NaBH 4 , B =
(b) A = NaBH 4 , B =
CH – CHO
||
CH – CO2H
||
(c) A = LiAlH 4 , B =
92.
(d) A = LiAlH 4 , B =
K
2 H 5 Br
Ph - CH 2 -CH - CH 3 ¾¾
® ¾C¾¾
¾® ( A)
|
OH
Product (A) in above reaction is:
(a) Ph - CH 2 -CH - CH 3 , (inversion)
|
(b) Ph - CH 2 -CH - CH 3 , (retention)
|
OEt
OEt
(c) Ph - CH 2 -CH - CH 3 , (racemic)
|
OEt
O
||
93.
(d) Ph - CH = CH - CH 3
Ph - C - O - H + CH 3 - O 18 - H
O
H+
( X ) + H 2O ; Identify X:
||
(a) X = Ph - C - O 18 - CH 3 (Trans esterification )
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O
||
(b) X = Ph - C - O 18 - CH 3 (Esterification reaction)
O
||
(c) X = Ph - C - O 18 - CH 3 (Saponification)
O
||
(d) X = Ph - C - O - CH 3 (Hydrolysis)
O
||
H
¾® R – O – C
NO2 ¾ ¾
O
||
94.
+
R - OH + H - O - C
NO2
Fastest rate of reaction will be when R is :
CH 3
|
(a) CH 3 -
(b) CH 3 - CH 2
(c) CH 3 - CH |
(d) CH 3 - C |
CH 3
95.
96.
Select the correct statement.
(a) Solvolysis of (CH 3 ) 2 C = CH - CH 2 - Cl in ethanol is over 6000 times greater than alkyl
chloride (25ºC)
(b) CH 3 - CH = CH - CH 2 - OH when reacts with HBr give a mixture of 1-bromo-2-butene
and 3-bromo 1-butene
(c) When solution of 3-buten-2-ol in aqueous sulphuric acid is allowed to stand for one
week, it was found to contain both 3-buten-2-ol and 2-buten-1-ol
(d) All of these
OH
OH
CH2 – OH
; Above transformation can be carried out by :
¾®
(a) H + D , Zn(Hg), HCl
(c) HIO 4 , H
97.
CH 3
+
(b) HIO 4 , LiAlH 4
(d) H + D , HIO 4
D
SOCl
O
NaBH
Zn
4
3
2
H 2C = CH - CH 2 - CH 2 -CH - CH 3 ¾ ¾¾
® ( A) ¾ ¾¾
¾
® (C )
¾® ( B ) ¾ ¾¾
(H O)
Pyridine
|
2
OH
C 5 H 9ClO
Compound (C) is :
OH
|
(a) CH 3 -CH - CH 2 -CH - CH 3
|
Cl
(b) HOCH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - Cl
Cl
|
(c) HO - CH 2 - CH 2 - CH 2 -CH - CH 3
(d) HO - CH 2 - CH 2 -CH - CH 2 - CH 3
|
Cl
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98.
Iodoform can be obtained on warming NaOH and iodine with :
O
||
(a) CH 3CH 2CH(OH)CH 3
(b) (CH 3 ) 2 CH C C 2H 5
(c) CH 3 — C — OCH 3
(d) (CH 3 ) 2 CHCH 2OH
O
Which of these is a reducing agent ?
(a) CrO 3 H +
(b) KMnO 4
(c) LiAlH 4
(d) O 3
||
99.
(i). (BH 3 )2
CH2
100.
¾ ¾¾¾¾¾
¾
- ® ( P ); Product ( P ) in the reaction is:
(ii). H 2O 2 OH
CH3
OH
CH2OH (b)
(a)
O
O
(c)
(d)
OH
CH 3
|
101.
Na Cr O
2 2 7
¾® ( P ); Product ( P ) in the reaction is:
CH 3 — C — CH 3 ¾ ¾¾¾
cool
|
OH
CH 3
CH 3
|
|
(a) CH 3 — C = CH 2
CH 3
|
(b) CH 3 — CH — CH 3
CH 3
|
(c) CH 3 — C — O — C — CH 3
102.
|
|
CH 3
CH 3
(d) No reaction
1, 2, 3 – butanetriol undergoes oxidative cleavage of HIO 4 . During this process
(a) 1 equivalent of HIO 4 consumed & HCO 2H & H 3C - C - CO 2H are formed
||
O
(b) 2 equivalents of HIO 4 consumed & HCO 2H, HCH = O & CH 3 - CH = O are formed
(c) 3 equivalents of HIO 4 consumed & HCO 2H (2 eq.) & 1 eq. of CH 3CO 2H are formed
(d) 2 equivalents of HIO 4 consumed & 2 eq. of HCO 2H & 1 eq. of CH 3 CH = O is formed
O
O
||
||
C – OCH3
CH3 – CO
4
¾(i)LiAlH
¾¾¾
® ( A) ; Product (A) of the reaction is :
103.
(ii)H 2O
OH
OH OH
(a)
(b)
( 96%)
O
OH CH OH
2
CH2 – OH
(c)
(d)
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O
O
||
104.
R - C - O - R ' + R ' ' OH
HÅ
||
R - C - O - R ' ' + R ' OH
Above reaction is/an example of :
(a) esterification
(c) trans-esterification
105.
(b) saponification
(d) hydrolysis
What is the major organic product of the following sequence of reactions ?
O
3
(CH 3 ) 2 CHCH 2OH ¾ PBr
¾¾
® ¾ Mg
¾
¾®
OH
H2C
CH2
H O+
3
¾ ¾¾
®?
|
(a) (CH 3 ) 2 CHCH CH 2CH 3
OH
(b) (CH 3 ) 2 CHCH 2CH 2OH
(c) (CH 3 ) 2 CHCH 2CHCH 3
(d) (CH 3 ) 2 CHCH 2CH 2CH 2OH
|
106.
The structure of the product formed in the reaction given below is :
H+
¾¾
®
D
OH OH
(a)
(b)
(c)
(d)
O
107.
CHO
|
2HIO 4
¾®
CH - OH ¾ ¾¾
|
CH 2 - OH
O
Products obtained in the above reaction are :
(a) HCHO , HCO 2H
(c) CO 2 ,2HCO 2H
108.
O
(b) HCHO, 2HCO 2H
(d) CO 2 , HCHO, HCO 2H
CHO
|
(CH - OH) 3 + 4HIO 4 ¾® Products obtained are :
|
CH 2 - OH
Aldo pentose
(a) 4HCO 2H, HCHO
(c) CO 2 , 4HCHO
109.
(b) 4CH 2O, HCO 2H
(d) CO 2 ,3HCO 2H, HCHO
CHO
|
4HIO 4
(i) (CH - OH) 3 ¾ ¾¾
¾® Product
|
CH 2 - OH
CH 2OH
|
5HIO 4
(ii) (CH - OH) 4 ¾ ¾¾
¾® Product
|
CH 2 - OH
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374
Ratio of moles of formic acid obtained in reaction (i) and reaction (ii) is :
(a) 3/4
(b) 4/5
(c) 1
(d) 5/4
110.
Which of the following compound gives 2HCHO, CO 2 , HCO 2 H when oxidised by periodic acid?
CH 2 _ OH
|
(a) (CH - OH) 2
|
CH 2 - OH
CH 2 - OH
|
C == O
(c) |
(CH - OH) 2
|
CH 2 - OH
CHO
|
(b) (CH - OH) 2
|
CH 2 - OH
CHO
|
C == O
(d) |
CH - OH
|
CH 2 - OH
111.
Hydration of 3-phenylbut-1-ene in dil. H 2SO 4 will give mainly :
(a) 3-Phenylbutan-1-ol
(b) 3-Phenylbutan-2-ol
(c) 2-Phenylbutan-2-ol
(d) 2-Phenylbutan-1-ol
112.
Decarboxylation of sodium salicylate with soda lime forms :
(a) Salicylic acid
(b) Phenol
(c) Benzene
(d) None of these
MeO – CH
|
CH – OH
|
xHIO 4
¾® What is the maximum value of (x) ?
CH – OH O ¾ ¾¾
|
CH – OH
|
HC
|
CH2 – OH
113.
(a) 1
(b) 2
(c) 3
(d) 4
CH2 – OH
O
CH2 – OH
114.
H+
CH – CO 2Et
(A)
LiAlH4
( B)
CH3
O
( C). Product C is :
O
(a)
(b)
CH2 – CH – OH
CH – CH 2 – OH
CH3
O
(c)
H3OÅ
OH
CH3
O
(d)
CH2 – CH 2 – OH
C – CH 3
CH3
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115.
CH2 – O
(A) + CH 2 - OH ¾ Pyridine
¾¾¾®
C=O;
CH2 – O
|
CH 2 -OH
Reactant A of the above reaction is :
O
||
(b) COCl 2
(a) CH 3 - C - CH 3
O
116.
O
O
O
(A)
O
(B)
CO2CH3
O
||
(d) CH 3 - C - OEt
O
||
(c) CH 3 - C - Cl
O
(C)
(D)
CH2 – OH
CO2CH3
O
O
CHO
CHO
Identify correct combination :
CH 2 - OH
(a) (A) = |
CH 2 - SH
(b) (B)= NaBH 4
(c) (C) = KMnO 4
(d) (D) = H 3O Å
117.
In the Libermann's nitroso reaction, sequential changes in the colour of phenol occurs as :
(a) Brown or red ¾® green ¾® deep blue (b) Red ¾® deep blue ¾® green
(c) Red ¾® green ¾® white
(d) White ¾® red ¾® green
118.
Ethanol when reacts with PCl 5 gives A, POCl 3 and HCl. A reacts with dry Ag 2O to form
B(major product) and AgCl. A and B respectively are :
(a) C 2H 5Cl and C 2H 5OC 2H 5
(b) C 2H 4 and C 2H 5OC 2H 5
(c) C 2H 6 and C 2H 5OC 2H 5
(d) C 2H 6 and C 2H 5NO 2
O
||
CH 3 -S - Cl
||
119.
120.
14
H OÅ
3
O
CH 3 - (CH 2 ) 3 - OH ¾ ¾¾¾
¾® ( A) ¾ KCN
¾¾® ( B ) ¾ ¾¾
® (C )
ET3 N
Product (C) is :
(a) CH 3 - (CH 2 ) 3 - CO 2H
(b) CH 3 - (CH 2 ) 3 - 14 CO 2H
(c) CH 3 - CO 2H
O
||
(d) CH 3 - C - O - H
14
Choose the best synthesis of phenyl n-propyl ether.
OH
(a)
1. Na metal
¾ 2.
¾¾¾¾¾¾
®
CH CH CH Br/
3
2
2
polar,aprotic solvent
(b) H C
3
OH
Na metal
¾1.
¾¾¾
¾®
2. Ph - Br
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O
CH3
OH
1. Na metal
(c)
3
2
H3C
OH
Na Cr O
H SO
2 2 7
2
4
¾ ¾¾¾¾¾
¾
® The product obtained is :
121.
HO
(a)
122.
Na metal
¾1.¾¾¾
¾®
2. HBr
(d)
¾ 2.
¾¾¾¾
¾®
CH CH - Br
O
O
O
(b) O
O
(c)
(d) None of these
H
CO2H
HO
What is true for the equilibrium reaction ?
O
O
||
||
cat.
CH 3 - C - OH + CH 3 - OH
CH 3 - C - O - CH 3 + H 2O
(a) The use of equimolar quantities of CH3OH and CH3COOH will give the greatest yield of
the ester at equilibrium
(b) Removal of water will increase the amount of ester at equilibrium
(c) Addition of CH3COOCH3 will cause the formation of equal an equal number of moles of
water
(d) Application of pressure increases the amount of ester at equilibrium
123.
PCC (Pyridinium chloro chromate) is a good reagent for which of the following transformations ?
O
OH
O
OH
(a)
(b)
OH
(c)
O
Cl
CO2H
CO2H
(d)
124.
How many primary alcohols (including stereoisomers) are possible with formula C 5H 12O ?
(a) Two
(b) Three
(c) Four
(d) Five
125.
1-Phenylethanol can be prepared by the reaction of benzaldehyde with the product obtained
in the reaction between:
(a) CH 3I and Mg
(b) C 2H 5I and Mg
(c) CH 3Br and AlCl 3
(d) CH 3OH and ZnCl 2
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126.
0.092 g of a compound with the molecular formula C 3H 8 O 3 on reaction with an excess of
CH 3MgI gives 67.00 mL of methane at STP. The number of active hydrogen atoms present in
a molecule of the compound is :
(a) one
(b) two
(c) three
(d) four
127.
Migratory aptitude of the following in decreasing order is :
Cl
Me
(c)
(d)
OMe
(a)
(b)
(a) a > c > b > d
(c) a > d > c > b
(b) a > d > b > c
(d) b > c > a > b
128. The major product formed in the reaction is :
H O+
O
O
(a)
3
®?
CH2R ¾ ¾¾
+ RCH 2OH
(b)
O
(c)
HO
O
HO
+ RCH 2OH
CHO
(d)
HO OH O
CH2R
CH2R
129.
Reaction of R-2-butanol with p-toluenesulphonyl chloride in pyridine then LiBr gives :
(a) R-2-butyl bromide
(b) S-2-butyl tosylate
(c) R-2-butyl tosylate
(d) S-2-butyl bromide
130.
Optically active 2-octanol rapidly loses its optical activity when exposed to :
(a) dilute acid
(b) dilute base
(c) light
(d) humidity
131.
If (±) 2-methyl butanoic acid were esterified by reaction with (±) 2-butanol, how many
optically active compounds would be present in the final equilibrium reaction mixture ?
(a) 2
(b) 3
(c) 4
(d) 6
O
OH
132.
Na2Cr2O7
PBr3
W
Mg
ether
X
(1) V
(2) H3O+
Y
CH3 — C — Cl
Z
V
Product Z of above reaction is :
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O
O
O – C – CH3
O – C – CH3
(a)
(b)
O
O
O – C – CH3
O – C – CH3
(c)
(d)
H
OH
C
4
¾ LiAlH
¾¾
¾
® (A) ; Identify the product :
133.
AlCl 3
(a) No reaction
H
(b)
H
O
||
(d) Ph — C — Ph
C
(c)
134.
H OÅ
(EtO) 2 CHCHO + CH 3MgI ¾ ¾3 ¾® (A)
Product obtained in the above reaction is :
OH
|
(b) CH 3 — CH — CHO
O O
|| ||
(a) CH 3 — C — C — H
O
||
(c) CH 3 — C — CH 2 — OH
135.
(d) CH 3 —CH — CH 2 — OH
|
OH
NaIO
KMnO
4
4
Reaction - (1): CH 3 — CH == CH — CH 3 ¾ ¾
¾
¾
® (A) ¾ ¾ ¾
¾
® (B) 2 mole
Cold
KMnO
NaIO
4
Reaction - (2): CH 3 — CH == CH — CH 3 ¾ ¾ ¾4¾ ¾¾
® (C) 2 mole
Product (B) and (C) respectively are :
(a) CH 3CHO, CH 3CO 2H
(b) CH 3CO 2H, CH 3CHO
(c) CH 3CHO in both reaction
(d) CH 3CO 2H in both reaction
OH
136.
TsCl
Pyridine, 25°C
A
LiAlH4
Pyridine, 25°C
B ; Product (B) is :
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Cl
(a)
137.
(b)
(c)
¾¾® HO – (CH 2 ) 6 – OH, this conversion can be achieved by
(a) O 3 , Zn, then LiAlH 4
(c) cold dil. KMnO 4 , HIO 4 , then LiAlH 4
138.
(d)
(b) O 3 H 2O 2 , then LiAlH 4
(d) All of these
Which of the following alcohol on treatment with HCl give 3-chloro-3-methyl cyclohexene
as a product ?
CH3
CH3
CH3
OH
(a)
(b)
(c)
(d) All of these
OH
OH
(a) RCO 3 H
¾ ¾ ¾ ¾ ¾ ¾ ¾+ ¾¾® (A); Product of the reaction is :
139.
(b) CH 3 MgBr (c) H , H 2O
CH3
OH
(a)
(b)
(c)
OH
Esterification (shown below) is a reaction converting a carboxylic acid to its ester. It involves
only the carbonyl carbon. Esterification of ( -) -lactic acid with methanol yields (+)-methyl
lactate. Assuming that there are no side reactions, what is true about this reaction ?
OH
OH
(a)
(b)
(c)
(d)
OH
CH 3OH
¾¾¾
¾®
HCl
O
141.
(d)
CH3
CH3
140.
OH
OH
OCH3
O
( -)
( +)
An S N 2 process has occurred, inverting the absolute configuration of the chiral center
An S N1 reaction at the chiral center has inverted the optical rotation
A diastereomer has been produced; diastereomers have different physical properties
including optical rotation
Optical rotation is not directly related to absolute configuration, so the change in sign of
rotation is merely a coincidence
Which of the following sets of reagents, used in the order shown, would successfully
accomplish the conversion shown ?
O
||
CCH3 ¾¾®
CH3
|
CHCH2CH2CH3
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(a) CH 3CH 2CH 2MgBr; H 3O + ; PCC, CH 2Cl 2
(b) CH 3CH 2CH 2MgBr; H 3O + ; H 2SO 4 , heat PCC, CH 2Cl 2
+
&& HCH 2CH 3 , B 2H 6 ; CH 3CO 2H
(c) (C 6 H 5 ) 3 P - C
+
&& HCH 2CH 3 ; H 2O
(d) (C 6 H 5 ) 3 P - C
O
||
CO2Et
142.
(2) D
O
||
O
||
O
||
CHO
(a)
143.
+
H 3O
¾(1)
¾¾
¾
¾® Product ; Product of the reaction is :
(b)
O
||
CH3
(c)
O
(d)
Which of the following compound on hydrolysis followed by heating gives a product, which
gives positive iodoform test?
CO2Et
O
||
C –CH3
(a) CH 3 - CH - C - CH 2 - CH 3
(b)
||
|
O
CO 2Et
O
O
||
||
C
– O – Et
(c) CH 3 - CH - CO 2Et
(d)
|
CO 2Et
144.
145.
Treatment of a 2° OH with CrO 3 H 2SO 4 yields an/a :
(a) aldehyde
(b) carboxylic acid
(c) ester
(d) ketone
Esterification of the acid P with the alcohols Q will give :
H
OH
CH3
CH3
CO2H
(S)-P
(±)-Q
(a) only one enantiomer
(c) a mixture of enantiomers
O
CO2Et
H O/D
146.
¾ ¾2 ¾
¾® product
EtO2C
(b) a mixture of diastereomers
(d) only one diastereomer
O
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Identify major product of the reaction, when the given compound is hydrolysed and heated
strongly:
CO2H
OH
OH
O
CO2H
(a)
(b)
(c)
(d)
O
HO2C
CO2H
OH
O
147.
find out the reactivity order with LiAlH 4 :
(a) A > B > C > D
(c) D > C > B > A
148.
(b) B > C > D > A
(d) B > D > C > A
Find out the reaction in which obtained product give positive isocyanide test:
(a)
(b)
(c)
(d)
149.
In the above given compound how many functional group reduced by LAH (Lithium
aluminium hydride ) and SBH (sodium borohydride) respectively ?
(a) 4, 4
(b) 4, 3
(c) 3, 4
(d) 4, 2
150.
An unknown compound (A) (molarmass = 180) on acylation gives a product (molar mass
= 390) than find the number of hydroxyl group present in compound (A).
(a) 5
(b) 6
(c) 10
(d) 1
151.
Which of the following compound is differentiated by NaHCO 3 as well as by NaOH ?
CH2—OH
OH
CO2H
OH
(a)
(b)
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CO2H
CH2—OH
OH
(c)
152.
(d)
Arrange the following compounds in order of their reactivity toward LiAlH 4 .
O
O
O
CH3
O
N
i
ii
iii
(b) i < iii < ii
(d) ii < iii < i
(a) i < ii < iii
(c) ii < i < iii
153.
OCH3
Choose the statement that is true about A , B and C in the following separation scheme.
Ether
layer
Naphthalene
Diethyl
Ether
..
N
Evaporate
A
HCl
Ether
layer
Aqueous
layer
H
tetrahydroisoquinoline
Evaporate
B
Make basic with
10% NaOH
H2O
Aqueous
layer
Evaporate
C
(a) A = tetrahydroisoquinoline, B = naphthalene and C = inorganic ions such as Na + and
Cl (b) A = naphthalene, B = tetrahydroisoquinoline and C = inorganic ions such as Na + and
Cl (c) A = inorganic ions such as Na + and Cl - , B = naphthalene and C = tetrahydroisoquinoline
(d) A = inorganic ions such as Na + and Cl - , B = naphthalene and C = tetrahydroisoquinoline
OH
O
xHI
CH2—OH ¾ ¾
¾® value of x is :
154.
O—CH3
CH2
(a) 2
(b) 3
CO2H
NaBH
(c) 4
(d) 5
r
4
¾¾¾
¾
® ( A) ¾ H¾
¾
® ( B)
D
155.
CH2—CHO
Cyclic
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Compound ( B ) is :
O
COOH
O
(a)
(b)
OH
O
O
(c)
(d) (a) and (c) both
156.
1-Phenoxypropane is treated with excess of conc. HI at 0° C and the mixture of products is
treated with thionyl chloride. The products formed are
(a) n-propanol + Chlorobenzene
(b) Phenol + n-propyl iodide
(c) n-propyl chloride + Chlorobenzene
(d) n-propyl chloride + Phenol
157.
Amongst the following compounds, the compound having the lowest boiling point is
(a)
(c)
(b)
OH
OH
(d)
O
OH
OH
158. Which statement/s are true about products P & Q.
(A) CH3—CH == CH—CH2—OH
(B) CH3—CH—CH == CH2
|
OH
SOCl2
ether
(6 member T.S.)
SOCl2
ether
(6 member T.S.)
P
Q
(a) P & Q are position isomers
(b) P show geometrical isomerism but Q not
(c) P º CH 3 — CH — CH == CH 2
Q º CH 3 — CH ==CH — CH 2 — Cl
|
Cl
(d) P º CH 3 — CH ==CH — CH 2 — Cl
O
|
159.
Q º CH 3 — CH — CH == CH 2
|
Cl
R
(i) BBr3
(ii) H2O
Product
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Which of the following is/are possible end product of the above reaction?
OH
|
Br
|
(a)
(b)
(c) R
(d) both (a) and (c)
Br
ANSWERS — LEVEL 1
1.
(c)
2.
(a)
3.
(b)
4.
(c)
5.
(b)
6.
(b)
7.
(b)
8.
(a)
9.
(b)
10.
(b)
11.
(b)
12.
(b)
13.
(a)
14.
(a)
15.
(a)
16.
(a)
17.
(d)
18.
(a)
19.
(b)
20.
(a)
21.
(a)
22.
(a)
23.
(d)
24.
(a)
25.
(b)
26.
(b)
27.
(b)
28.
(b)
29.
(c)
30.
(c)
31.
(b)
32.
(b)
33.
(a)
34.
(b)
35.
(b)
36.
(c)
37.
(c)
38.
(c)
39.
(d)
40.
(c)
41.
(b)
42.
(b)
43.
(d)
44.
(d)
45.
(b)
46.
(a)
47.
(b)
48.
(b)
49.
(a)
50.
(b)
51.
(a)
52.
(c)
53.
(c)
54.
(c)
55.
(b)
56.
(a)
57.
(d)
58.
(c)
59.
A-d
59.
B-b
59.
C-a
60.
(c)
61.
(c)
62.
A-b
62.
B-b
63.
(b)
64.
(c)
65.
(b)
66.
(a)
67.
(a)
68.
(d)
69.
(a)
70.
(c)
71.
(b)
72.
(d)
73.
(d)
74.
(c)
75.
(b)
76.
(d)
77.
(c)
78.
(c)
79.
(d)
80.
(c)
81.
(c)
82.
(d)
83.
(a)
84.
(b)
85.
(b)
86.
(c)
87.
(c)
88.
(b)
89.
(d)
90.
(a)
91.
(c)
92.
(b)
93.
(b)
94.
(a)
95.
(d)
96.
(b)
97.
(c)
98.
(a)
99.
(c)
100.
(a)
101.
(d)
102.
(b)
103.
(c)
104.
(c)
105.
(d)
106.
(c)
107.
(b)
108.
(a)
109.
(c)
110.
(d)
111.
(c)
112.
(b)
113.
(b)
114.
(b)
115.
(b)
116.
(d)
117.
(b)
118.
(a)
119.
(b)
120.
(a)
121.
(a)
122.
(b)
123.
(b)
124.
(d)
125.
(a)
126.
(c)
127.
(b)
128.
(c)
129.
(d)
130.
(a)
131.
(c)
132.
(b)
133.
(c)
134.
(b)
135.
(a)
136.
(c)
137.
(d)
138.
(d)
139.
(b)
140.
(d)
141.
(c)
142.
(b)
143.
(b)
144.
(d)
145.
(b)
146.
(c)
147.
(b)
148.
(a)
149.
(d)
150.
(a)
151.
(c)
152.
(d)
153.
(b)
154.
(b)
155.
(a)
156.
(b)
157.
(c)
158. (a,c) 159.
(d)
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385
Level - 2
1.
Consider the pairs of ethers, numbered I through V, shown below. To the right of each pair is
a description of reaction conditions to be applied to each. One compound of the pair will
react more rapidly than the other.
Which ether of the two will be more rapidly cleaved?
Write your answer in box.
(A)
Ether Pairs
(B)
Cleavage Conditions
H3C
O—CH(CH3)2 &
I.
H3C
H3C
II.
O—CH3
O—C(CH3)3 &
H3C
O—
C2H5
O—CH3
C2H5
O
&
IV.
V.
OH
&
O
O
Treated with H 2SO 4
in CH 3CN, 40°C
Treated with H 2SO 4
in CH 3CN, 40°C
III.
CH3O
Treated with HBr in
CH 3CN, 40°C
OH
CH(CH3)2 &
O
OCH3
O
CH(CH3)2
Treated with 5% aqueous
H 2SO 4 , 25°C
Treated with 5% aqueous
H 2SO 4 , 25°C
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2. Comprehension
(a) CH 3 - CH 2 - CH 2 - CH 2 - CH 2 - OH
(c) CH 3 - CH 2 -CH - CH 2 - CH 3
|
OH
(b) CH 3 - CH 2 - CH 2 - CH - CH 3
|
OH
CH 3
|
(d) CH 3 - CH 2 -C - OH
|
CH 3
CH 3
|
(e) CH 3 -CH - CH 2 - CH 2 - OH
CH 3
|
(f) CH 3 -CH -CH - CH 3
|
OH
CH 3
|
(g) HO - CH 2 - CH - CH 2 - CH 3
CH 3
|
(h) CH 3 -C - CH 2 - OH
|
CH 3
Above compounds (a) to (h) are isomers of C 5H 12O.
Based on the above isomer answer the following (A to F).
A.
Which isomer is most reactive towards dehydration by conc. H 2SO 4 ?
B.
Which isomer will undergo rearrangement when treated with conc. H 2SO 4 ?
C.
Which isomers on dehydration with conc. H 2SO 4 give alkene which is capable to show
geometrical isomerism ?
D.
Which isomer is least acidic ?
E.
Which isomers on dehydration give most stable alkene ?
F.
Which isomer on dehydration with conc. H 3PO 4 undergo maximum rearrangement ?
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3. Comprehension
R — CH3
(alkane lowest
oxidation no.)
[O]
[H]
R — CH2 — OH
alcohol
[O] = Oxidation
[O]
[H]
RCHO
aldehyde
[O]
[H]
RCO2H
(acid highest
oxidation no.)
[H] = Reduction
Consider the above sequence and answer A to F.
A.
Conversion (CH 3 - CH 3 ¾® CH 3 - CH 2 - OH) alkane ¾® alcohol is achieved by:
(a) Br 2 hn, alc. KOH
(c) Br 2 CCl 4 , LiAlH 4
(b) Br 2 hn, aq. KOH
(d) Br 2 CCl 4 , NaBH 4
B.
Conversion R - C H 2 - OH ¾® R - CHO can be done by:
(b) Cu, 300ºC
(a) PCC CH 2Cl 2
(c) CrO 3
(d) All of these
C.
Conversion R - CHO ¾® R - CO 2H can be done by:
(a) KMnO 4
(b) H 2CrO 4
(c) K 2Cr 2O 7
(d) All of these
D.
Conversion R - CO 2H ¾® R - CHO can be done by:
(a) LiAlH 4
(b) NaBH 4
(c) DIBAL – H
(d) All of these
E.
Conversion R - CHO ¾® R - CH 2 - OH can be done by:
(a) LiAlH 4
(b) NaBH 4
(c) H 2 Ni
(d) All of these
F.
Reduction R - CH 2 - OH ¾® R - CH 3 can be done by:
(a) LiAlH 4
(b) NaBH 4 - AlCl 3
(c) H 2 - Ni
(d) Red P + HI
4.
Which of the following is true for 3-methylbutanal ?
a. This compound may be classified as an aldehyde.
b. This compound may be classified as a ketone
c. An aldol reaction takes place on treatment with NaOH solution.
d. There is no reaction with LiAlH 4 in ether solution.
e. An excess of CH 3 MgBr in ether reacts to give 4-methyl-2-pentanol.
f.
Wolff-Kishner reduction gives butane.
g. This compound is an isomer of 3-pentanone.
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5.
This problem is an introduction to the planning of multistep syntheses.
For use, you have six reactant compounds (A through F) ; and eight reagents (1 through 8),
shown below.
Following these lists, five multistep syntheses are outlined. For each of these, certain
reactants or reagents must be identified by writing an appropriate letter or number in
designated answer boxes. Write a single letter or number, indicating your choice of the best
reactant or reagent, in each answer box.
Reactant Compounds :
(A)
OH
(B)
(C)
O
(F)
(2) PCC [CrO 3 in pyridine + HCl]
(3) Sodium hydride NaH
(5) Thionyl chloride SOCl 2
(7) Aluminium trichloride AlCl 3
1.
O
O
O
(E)
(D)
Reagents :
(1) Jones’ reagent [Na 2Cr 2O 7 in H 3O+ ]
CH2 – OH
O
O
O
(4) Sodium borohydride NaBH 4
(6) Phosphorus tribromide PBr 3
(8) Magnesium turnings in ether
(1) Reagent
(2) reactant
¾¾¾ ¾(+)
¾¾¾¾®
(3) H3O
C9H12O2
O
O
Reagent
¾¾ ¾¾®
H
O
2.
Reactant
C
3.
Reagent
¾¾ ¾¾®
OH
C3H6O2
(1) Reagent
(2) Reagent
¾¾ ¾ ¾ ¾¾®
(3) CO2
(4) H3O(+)
C6H10O2
Reactant Reagent
4.
¾¾ ¾ ¾ ¾¾® C3H6O
C
Reactant
5.
B
(1)Reagent
¾¾ ¾ ¾ ¾¾®
(2)Reagent
(1) Reagent
¾¾¾¾¾¾®
(2) Reactant
Reagent
heat
(1) NaOH solution
(2) Reagent
¾ ¾ ¾ ¾ ¾¾®
(3) Reactant
C3H7Br
O
(1) Reactant
¾¾ ¾ ¾ ¾¾®
heating with
catalytic acid
(1) Reagent
(2) Reactant
¾ ¾ ¾ ¾ ¾¾®
(3) H3O(+)
O – CH2CH2CH3
OCOCH3
OCOCH3
OH
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6.
Which of the following is true for 3-methyl-2-butanone?
a. It may be prepared by CrO 3 oxidation of 2-methyl-2-butanol.
b. Its reaction with NaBH 4 gives a secondary alcohol.
c. It may be prepared by acidic Hg 2+ catalyzed hydration of 3-methyl-1-butyne.
d. It forms a silver mirror on treatment with [Ag(NH 3 ) 2 ]+ .
e. This compound is an isomer of 4-penten-1-ol.
7.
Which of these methods would serve to prepare 1-phenyl-2-propanol?
a. Addition of benzyl Grignard reagent to acetaldehyde (ethanal).
b. Addition of phenyl lithium to propylene oxide (methyloxirane).
c. Addition of phenyl Grignard reagent to acetone (2-propanone).
d. Acid-catalyzed hydration (addition of water to) of 2-phenyl-1-propene.
e. Addition of methyl Grignard reagent to acetophenone (methyl phenyl ketone).
f.
8.
Addition of methyl Grignard reagent to phenylacetaldehyde.
Match the Column (I) and (II).
Column (I)
Column (II)
Reaction
Name of Reaction
+
¾ H¾
¾®
(a)
D
OH
(p)
Pinacol-Pinacolone rearrangement
OH
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2
¾ NaNO
¾¾
¾
®
(b)
2HCl
OH
(q)
Semi-Pinacol reaction
(r)
Pinacolic-Diazotization
(s)
Pinacol fashion reaction
NH2
+
¾ H¾
¾®
D
(c)
O
¾(1)TsCl,
¾ ¾¾®
(d)
(2)Et 3 N, D
OH
9.
OH
Match the Column (I) and (II).
Column (I)
Column (II)
Reactant
Products
CH3
(a)
OH
2
CH3
(b)
(c)
(d)
OH
CH3
OH
CH3
CH 3OH
¾ H¾SO
¾ Conc.
¾¾®
4
¾(1)NaH
¾¾
¾®
(2) CH 3 I
(1) HBr
¾¾¾
¾®
(2) Mg
(3) CH 3 I
CH3
¾(1)Na
¾¾
®
14
OH
(p)
14
OCH3
CH3
(q)
CH3
CH3
(r)
OCH3
CH3
(s)
(2)C H 3 I
OCH3
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10.
CH2 – OH
C == O
Reaction 1.
HO
H
H
OH
OH
H
5HIO4
CH2OH
CHO
Reaction 2.
HO
H
H
H
H
OH
OH
OH
5HIO4
CH2OH
Ratio of moles of formaldehyde obtained in the reaction (1) and reaction (2) ?
11. Comprehension
Di-tert-glycols rearrange in the presence of acid to give a-tertiary ketones. The trivial name
of the simplest glycol of this type is pinacol, and this type of reaction therefore is named
pinacol rearrangement (in this specific case, the reaction is called a pinacol-pinacolone
rearrangement). The rearrangement involves 4 steps. one of the hydroxyl groups is
protonated in the first step. A molecule of water is eliminated in the second step and a
tertiary carbocation is formed. The carbocation rearranges in the third step into a more
stable carboxonium ion via a [1, 2] rearrangement. In the last step, the carboxonium ion is
deprotonated and the product ketone is obtained.
Me Me
Me Me
HO
OH
Me Me
H2SO4
(I)
Me Me
Å
HO
OH2
Me Me
– H2O
(II)
HO
Å
Å
1,2-shift
(III)
O
Me
Me
Me
Me
Me
Me
Me
Me Me
Pinacol
O–H
(IV)
– HÅ
Me
Pinacolone
A.
What is R.D.S. of pinacol-pinacolone rearrangement ?
(a) I step
(b) II step
(c) III step
(d) IV step
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Et Ph
B.
HO
CH3 Ph
OH + HO
OH
H2SO4
D
CH3 Ph
Et Ph
How many products obtained in above reaction ?
(a) 1
(b) 2
(c) 3
(d) 4
OH
CH2–Cl ¾ AgNO
3
¾¾
¾
®P
C.
D
Product 'P' is :
O
O
O
O
Cl
(a)
(b)
(c)
(d)
CH3 CH3
D.
CH3
CH3
NaNO2
HCl
(A)
OH NH2
Product (A) is :
O CH 3
|| |
(a) CH 3 — C — C — CH 3
|
CH 3
CH3 CH3
(b) CH3
CH3
OH OH
(c)
(d) None of these
Subjective Problems
O
CH==O
1.
of PCC
( A) ¾ 4¾moles
¾¾
¾¾®
CH==O
O
Maximum number of moles of Ac 2O consumed by reactant ( A) is :
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ANSWERS — LEVEL 2
1.
I – B; II – A; III – A; IV – B; V – B
2.
A – d; B – a, c, e, f, g, h; C – a, b, c; D – d; E – d, e, f, g, h; F – e
3.
A – b; B – d, C – d, D – c, E – d; F – d
4.
a, c, e, g
CH2 – OH
5.
(1) Reagent 3
(2) reactant d
¾¾¾ ¾(+)
¾¾¾¾®
(3) H3O
C9H12O2
O
O
Reagent 2
¾¾ ¾¾®
H
O
Reactant
C
Reagent 1
¾¾ ¾¾®
OH
C3H6O2
(1) Reagent 6
(2) Reagent 8
¾¾ ¾ ¾ ¾¾®
(3) CO2
(4) H3O(+)
C6H10O2
Reactant Reagent 2
¾¾ ¾ ¾ ¾¾® C3H6O
C
Reactant
B
(1) Reagent 4
¾¾ ¾ ¾ ¾¾®
(2) Reagent 6
(1) Reagent 5
¾¾¾¾¾¾®
(2) Reactant A
Reagent 7
heat
+&
O – CH2CH2CH3
OCOCH3
(1) NaOH solution
(2) Reagent 4
¾ ¾ ¾ ¾ ¾¾®
(3) Reactant F
C3H7Br
O
(1) Reactant C
¾¾ ¾ ¾ ¾¾®
heating with
catalytic acid
OCOCH3
(1) Reagent 8
(2) Reactant C or F
¾ ¾ ¾ ¾ ¾¾®
(3) H3O(+)
OH
6.
b, c, e
7.
a, b, f
8.
a – p, b – r, c – s, d – q
9.
a – s, b – r, c – q, d – p
Ratio of reaction I and II = 2
11.
A – b; B – b; C – c; D – a
10.
Subjective Problems
1. 4
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7
ALDEHYDES AND KETONES
Level - 1
N H
KOH H O
4
2
¾ ¾2 ¾
¾¾¾
¾®
1.
(Wolff - Kishner reduction)
(a)
( A) ; Product A is :
major
(b)
OH
Cl
O
(c)
O
(d)
NO2
NO2
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O
C — CH3
CH2 — CH3
2.
CH2 — CH2 — NMe3
CH2 — CH2 — NMe3
Above conversion can be achieved by :
(a) Wolf-Kishner reduction
(c) LiAlH 4
(b) Clemmensen reduction
(d) NaBH 4
O
3.
CH3 ¾ C ¾ CH2 ¾ CH2 ¾ CH ¾ CH2 ¾¾® CH3 ¾ (CH2)3 ¾ CH ¾ CH2
O
O
Above conversion can be achieved by :
(a) Wolff- Kishner reduction
(b) Clemmensen reduction
(c) HS — CH 2 — CH 2 — SH, following by Raney Ni
(d) None of these
O
C — CH3
Zn(Hg)
4.
¾¾¾
¾® ; Product of the Clemmensen reduction is :
HCl
NO2
OH
CH2 — CH 3
(a)
CH2 — CH 3
CH — CH3
(b)
(c)
NO2
5.
OH
CH2 — CH3
(d)
NH2
NO2
NO2
OH
O
OH
|
||
|
CH 3 — CH — CH 2 — CH 2 — C — CH 3 ¾® CH 3 — CH — (CH 2 ) 3 — CH 3
Above conversion can be achieved by :
(a) Wolff-Kishner reduction
(c) LiAlH 4
(b) Clemmensen reduction
(d) NaBH 4
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O
CH2 — CH3
C — CH3
g)
Zn(H
HCl
NH —
2 NH
2
HO –
/D
6.
CH2 — CH3
CH2 — CH3
(A)
(B)
Cl
(Q)
OH
(P)
OH
Cl
(R)
Identify product (A) & (B) from the given product P , Q , R :
(a) A = P , B = Q
O
(b) A = Q , B = R
(c) A = Q, B = P
(d) A = R , B = P
C — CH3
Zn(Hg)
HCl
¾¾¾
¾® ( A) ; Identify the A.
7.
HO
CH2 — CH3
(a)
(b)
HO
Cl
OH
(c)
(d)
Cl
O
C — CH3
N 2H 4
¾ ¾ ¾ ¾ ¾- ¾ ¾ ¾¾® (A) ; Product (A) is :
8.
HO , D
(Wolff - Kishner reduction)
CH2 — CH2 — Br
CH2 — CH3
(a)
(b)
CH2 — CH2 — OH
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(c)
(d)
CH2 — CH2 — Br
CH — CH 3
Br
9.
;
Above conversion can be carried out by :
(a) Clemmensen reduction
(c) LiAlH 4
10.
(b) Wolff-Kishner reduction
(d) NaBH 4
Increasing order of equilibrium constants for the formation of a hydrate:
O
O
O
NH2
O2 N
NH2
(I)
(II)
(a) IV < III < II < I
(c) I < II < III < IV
11.
O
(IV)
(b) IV < III < I < II
(d) II <III < I < IV
HgSO
4
OCH3 ¾¾¾®
CººC
(III)
dil. H2SO4
(A)
Product (A) is:
Major product
O
(a)
C—CH2
OCH3
(b)
C—CH2
OCH3
OH
O
(c)
CH2—C
OCH3
(d)
CH2—CH
OCH3
OH
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H O
¾ ¾2¾® (A)
12.
Predict the product of hydrolysis of the above molecule.
O
CO2H
(a)
(b)
(c)
(d)
OH
OH
OH
OH
13.
, This conversion can be achieved by :
O
OH
+
(a) Me 2 CO H , H 3 O
Å
, KMnO 4 HO -
(c) KMnO 4 NaO 4 , Me 2 CO H + , H 3 O +
14.
O
(a) 2-4-DNP
(c) Lucas reagent
(b) Me 2 CO H + , KMnO 4 , H 3 O +
(d) KMnO 4 NaIO 4 , H 3 O + , Me 2 CO H +
H OÅ
¾ ¾3 ¾
¾® A + B. Compound (A) & (B) can be differentiated by:
(b) Fehling solution
(d) NaHSO 3
O
||
¾ ¾ ¾ ¾ ¾ ¾¾® ( A) + H — C — OMe ; Product (A) is :
HOH, H + catalyst
15.
20°C,15 min
(a)
(b)
(c)
Methyl formate
(d)
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P
16.
Q
R
O
O
Reagents to carry out above conversion, P, Q, R respectively are :
(a) H 2 C == CH — CH 2 — Br,(HO Q ),[HO Q , D ], Wacker-process
(b) H 2 C == CH — CH 2 — Br(HO Q ), Wacker-process, HO Q , D
(c) Wacker process, H 2 C == CH — CH 2 — Br(HO Q ),HO Q ( D )
(d) Wacker process, HO Q ( D ),H 2 C == CH — CH 2 — Br(HO Q )
-
CO2
O
R
17.
O
C¾O¾O¾H
+
¾®
Above reaction is a Baeyer Villiger rearrangement of an asymmetric ketone with magnesium
mono peroxo pthalate hexahydrate (in the drawing, Mg +2 is omitted for clearity) Identify
major product.
O
O
R
OH
R
O
(a)
(b)
(c)
(d)
18.
,
Above compounds can be differentiated by following reagent:
(a) 2-4 DNP (Brady reagent)
(c) Lucas reagent
OH
OH
19.
PCC (excess)
(b) Tollen's reagent
(d) NaHSO 3
(A)
OH
OH
1 equivalent
H+
(B)
Product (D) will be :
OH
OH
CH3MgBr
(C)
H3O+
NaBH4
(D)
OH
CH ¾ CH3
(a)
OH
(b)
OH
OH
OH
(c)
OH
(d)
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20.
BH3,THF
–
H2O2,OH
(P)
Hg(OAc)2,H2O
NaBH ,HOs
(R)
Pyridinium Chloro Chromate (PCC)
CH2Cl2
(Q)
CH3—CH == CH2
Pyridinium Chloro Chromate (PCC)
CH2Cl2
4
(S)
Relationship between products (Q ) and ( S) is:
(a) Positional isomer
(c) Stereoisomer
21.
(b) Chain isomer
(d) Functional isomer
1. Al(Hg), benzene, heat
2. H 2O, heat
In the reaction,
¾® X, the product (X) is :
O ¾¾¾¾¾¾¾¾
(a)
(b)
O
HO
O
(c)
22.
OH
(d)
O
Rank the following in order of increasing value of the equilibrium constant for hydration,
K hyd. (smallest value first).
O
O
O
1
(a) 1 < 2 <3
(b) 3 < 1 < 2
(CH3)3CCC(CH3)3
2
3
(c) 2 < 1 < 3
(d) 2 < 3 < 1
O
23.
O
S
¾¾®
S
O
Above conversion can be achieved by:
(a) Zn(Hg ), HCl
(c) LiAlH 4
(b) NH 2 — NH 2 KOH D
(d) H 2 Ni
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24.
Which sequence represents the best synthesis of hexanal ?
CH 3 CH 2 CH 2 CH 2 CH 2 CH == O
Hexanal
(a) 1. CH 3 CH 2 CH 2 CH 2 Br + NaC ºº CH
O
||
(b) 1. CH 3 CH 2 CH 2 CH == CH 2 + CH 3 C OOH
2. H 2 O, H 2 SO 4 ,HgSO 4
2. CH 3 MgBr , diethyl ether
3. H 3 O +
4. PCC, CH 2 Cl 2
O
||
(c) 1. CH 3 CH 2 CH 2 CH 2 C CH 3
O
||
2. CH 3 C OOH
4. H 2 O
O
(d) 1. CH 3CH2CH2CH2MgBr + H 2C — CH 2
O
2. H 3 O +
3. LiAlH 4
3. PCC, CH 2 Cl 2
5. PCC, CH 2 Cl 2
HNO
Ca(OH)
3
2
¾¾¾
¾
®( A) ¾ ¾ ¾¾
®( B ), Product (B) in this reaction is :
25.
O
O
O
O
(a)
(b)
(c)
CH2OH
26.
HO
H
H
H
OH
OH
CH2 — OH
(d)
CH2O
(?)x
HO
H
H
H
O
OH
CH — Ph
,
CH2 — OH
Compound (x) in the above reaction is :
O
||
(a) Ph — C — CH 3
O
||
(c) Ph — CH 2 — C — H
O
||
(b) Ph — C — H
O
||
(d) Ph — CH 2 — C — CH 3
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27.
O
||
NaNO 2
AC O
H O+
®( A) ¾ ¾2¾
¾®( B ) ¾ ¾3 ¾®(C )
Ph — C — CH 3 ¾ ¾ ¾¾
heat
HCl
Product (C) of the above reaction is :
O
||
(b) Ph — C — CO 2 H
O
||
(d) Ph — C — CH 2 OH
(a) Ph — CO 2 H
O O
|| ||
(c) Ph — C — C — H
O
||
H— C — H
AgNO
2
¾¾¾¾
¾® ( A) ¾ ¾ ¾
¾
® ( B ) ; Product (B) of the reaction is :
28.
2HCl
(a) Ph — CH 2 — NO 2
(c) Ph — CHO
O
Br
(b) Ph — CH 2 — ONO
(d) Ph — O — N == O
2
¾¾
¾
®
29.
( A) ;
0.75 mole %, (100%)
AlCl 3 Et 2O
Product (A) of the above reaction is (bromination occur not in the benzene ring) :
O
Br
O
(a)
(b)
Br
O
O
Br
CH3
C
(c)
(d)
Br
+ive Iodoform test
–ive Tollens test
30.
C6H12O3
A
H O
2
¾¾¾¾
¾¾® Positive Tollens test
drop of H SO
2
4
Compound (A) is :
O
||
(a) CH 3 — C — CH — CH 2
|
|
OCH 3 OCH 3
O OCH 3
|| |
(b) CH 3 — C — C — CH 3
|
OCH 3
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O
||
(c) CH 3 — C — CH 2 — CH — OCH 3
|
OCH 3
31.
O
NH — NH
3
2
2
C 16 H 16 ¾ ¾
¾
® ( B) ¾ ¾ ¾
¾¾
®
(A)
C 8 H 8O
Ph
(a)
C == C
Ph
Ph
(c) C=
CH3
HO - D
O
||
(d)H — C — CH 2 — CH 2 — CH — OCH 3
|
OCH 3
; Reactant (A) in this reaction is :
Ph
(b) C=
CH3
CH3
CH3
=C
CH3
Ph
Ph
=C
(d) both (b) and (c)
CH3
P C7H14O2
H3
32.
OÅ
O—O—H
+ive
Iodoform
test
1-methyl1-cyclohexyl
hydrogenperoxide
+ive
2-4 DNP
test
+ive test with
CrO3
Compound (P) is :
O
||
(a) CH 3 — C — CH 2 — CH 2 — CH 2 — CH — CH 3
|
OH
O
OH
||
|
(b) CH 3 — C — CH 2 — CH — CH 2 — CH 2 — CH 3
O
||
(c) CH 3 — C — CH 2 — CH 2 — CH 2 — CH 2 — CH 2 — OH
O
OH
||
|
(d) CH 3 — C — CH — C — CH 3
|
|
CH 3 CH 3
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33.
Correct order of reactivity of following compounds towards Grignard reagent?
O
||
H — C— H
(II)
O
||
CH 3 — C — H
(I)
(a) I > II > III
O
CH3—C
(III)
(b) II > I > III
(c) II > III > I
(d) I > III > II
CH2 ¾
34.
CH3 ¾ CH ¾ CH ¾ CH2 ¾ OH ¾ HCHO
¾¾
¾® ( A) ; Product (A) is :
TsOH, D
93%
OH
(a)
(b)
(c)
(d)
O
35.
I
(CH3)3CO ¾ C ¾ CH2 ¾ CH2 ¾ CH —
OH
KOH
¾®
— OCH2CH2CH3 ¾H¾
2O D
OCH3
Total number of products obtained in above reaction is :
(a) 2
(c) 4
(b) 3
(d) 5
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36.
What reagent and/or reaction conditions would you choose to bring about the
following conversion?
O
CH == O + HOCH 2 CH 2 OH
¾®
O
(a) 1. LiAlH 4 , 2. H 2 O
(c) H 2 O, NaOH, heat
O
||
(b) H 2 O, H 2 SO 4 , heat
(d) PCC, CH 2 Cl 2
MeI excess
KH excess
¾¾¾¾
¾® 81% yield ; Product of the reaction is :
37.
O
||
(a)
38.
HO
(b)
O
||
C
O
||
O
||
O
||
(c)
(d)
¾® HO
The above reduction can be best carried out by :
(a) Clemmensen reduction
(c) NaBH 4
39.
(b) Wolff-Kishner reduction
(d) None of these
HgSO
4
CH 3 — C ºº CH ¾ ¾ ¾
¾
® ( A)
dil. H 2SO 4
(1) BH ×THF
CH 3 — C ºº CH ¾ ¾ ¾3¾ ¾® ( B )
(2) H 2O 2 / HO -
Product ( A) and ( B ) is differentiated by:
(a) 2-4-DNP
(b) NaOI
(c) Na-metal
(d) NaHSO 3
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O
HCN
LiAlH
NaNO
HCl
4
2 ® (C )
¾ ¾¾® ( A) ¾ ¾ ¾
¾
® ( B ) ¾ ¾ ¾¾
40.
End product (C) in above reaction is :
O
(a)
41.
OH
OH |
CH2
O
O
(b)
(c)
(d)
Compound (X) C 4 H 8 O, which reacts with 2, 4-DNP derivative and gives negative haloform
test is :
O
||
(b) CH 3 — CH — CHO
(a) CH 3 — C — CH 2 — CH 3
|
CH 3
OH
|
(d) CH 3 — CH 2 — CH — CH 3
OH
(c)
42.
When a nucleophile encounters a ketone, the site of attack is :
(a) the carbon atom of the carbonyl
(b) the oxygen atom of the carbonyl
(c) both the carbon and oxygen atoms, with equal probability
(d) no attack occurs as ketones do not react with nucleophiles
43.
The correct order of rate of reaction toward nucleophilic addition reaction:
CHO
CHO
CHO
O
||
O
C – Ph
||
CH3 - C - Et
NO2
OMe
(a)
(b)
(d )
(c)
(a) a > b > c > d > e
(c) a > d > e > b > c
(e)
(b) a > b > d > c > e
(d) a > b > e > d > c
O
44.
The structure
OH would be best classified as a(an) :
H
(a) Acetal
45.
(b) Hemiacetal
(c) Hydrate
(d) Cyanohydrin
Which of the following pairs of reactants is most effective in forming an enamine ?
O
||
O
||
(a) CH 3 CH 2 C H + [(CH 3 ) 2 CH]2 NH
(b)
+ CH 3 — NH — CH 3
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O
||
(c) (CH 3 ) 3 CC H + (CH 3 ) 2 NH
46.
(d) None of these form an enamine.
The reaction of C 6 H 5 CH == CHCHO with LiAlH 4 gives :
(a) C 6 H 5 CH 2 CH 2 CH 2 OH
(b) C 6 H 5 CH == CHCH 2 OH
(c) C 6 H 5 CH 2 CH 2 CHO
(d) C 6 H 5 CH 2 CHOHCH 3
O
+
NaBH 4
H
¾ ¾ ¾¾
® ( A) ¾ ¾¾® ( B ) ; Product (B) of the reaction is :
47.
D
O
O
O
(a)
O
O
(b)
(c)
(d)
OH
48.
OH
Which of following compound is hemiacetal ?
HO
OMe
OH
O
(a)
(b)
H
OH
(c)
(d) all of these
O
49.
CH 3I
LDA
® 71% ; End product of the reaction will be :
Ph — CH 2 — C ºº N ¾ ¾
¾® ¾ ¾¾
THF
(a) Ph — CH 2 — CH 2 — NH 2
(c) Ph — CH — C ºº N
(b) Ph — CH 2 — NH 2
(d) Ph — CH == C == N — CH 3
|
CH 3
O
||
50.
Ph — CH == CH — C — CH 3 ¾® Ph — CH == CH — CO 2 H
Above conversion can be achieved by :
(a) KMnO 4 , D followed by H +
(c) H 2 Pt
OH
(b) I 2 NaOH followed by H +
(d) LiAlH 4
Å
H O
¾ ¾3 ¾
¾® Products ; Product of the reaction is/are :
51.
O
O
CH2
OH
OH
(a)
(b)
OH
OH
OH
(c) HCHO
(d) Both (a) and (c)
OH
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408
O
||
SeO
2 ® (A); Product (A) of the reaction is :
¾ ¾¾
52.
O
||
O
||
OH
(a)
O
||
O
(b)
O
||
O
||
(c)
O
(d)
CH3
Br + NaOH
COCH3 ¾ ¾2 ¾ ¾¾® (A) + CHBr3 ; Product (C) of the reaction is :
53.
D
+
O
||
O
||
(a)
(C)
¾H
¾®
D
(b)
O
O
O
||
(c)
O
O
54.
O
||
Br
CH3
CBr3
(d)
Å
H O
¾ ¾3 ¾
¾® (A) + 2 Glycol
Product (A) of the reaction will be :
O
O
||
||
(a) CH 3 — CH 2 — C — CH 2 — C — CH 2 — CH 3
O
O
||
||
(b) CH 3 — CH 2 — C — CH 2 — CH 2 — C — CH 3
O
O
||
||
(c) CH 3 — CH 2 — C — CH 2 — C — CH 3
O
O
||
||
(d) CH 3 — C — CH 2 — C — CH 3
O
||
55.
R - NH 2
R — C — H ¾ ¾ ¾¾
® R — CH ==N — R. This reaction gives best yield at :
(a) pH 1 - 2
56.
(b) pH 4 - 5
(c) pH 10 - 11
(d) pH 13 - 14
An aromatic compound A of the molecular formula C 8 H 10 O on reaction with iodine and
dilute NaOH gives a yellow precipitate. The structure of the compound is expected to be:
(a)
(b) C 6 H 5 CHOHCH 3
C—CH3
O
(c) CH3
CH2OH
(d) CH3
OH
CH3
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409
57.
Compound A (molecular formula C 3 H 8 O) is treated with acidified potassium dichromate to
form a product B(molecular formula C 3 H 6 O). B forms a shining silver mirror on warming
with ammonical silver nitrate, B when treated with an aqueous solution of NH 2 NHCONH 2
and sodium acetate gives a product C. Identify the structure of C.
(a) CH 3 CH 2 CH == NNHCONH 2
(b) CH 3 C == NHHCONH 2
|
CH 3
58.
59.
(c) C H 3C == NCONHNH 2
(d) CH 3 CH 2 CH == NCONHNH 2
|
CH 3
In the reaction, the acid obtained will be :
-OH
CH3CHO + HCN ¾® CH3CH(OH)CN ¾ H
¾¾
¾® CH3CH(OH)COOH
(a) D-isomer
(b) L-isomer
(c) (80%D + 20%L) mixture
(d) (50%D + 50%L) mixture
In the following sequence :
NaCN
acetic anhydride
Ni H
2 ® (ii) ¾ ¾ ¾ ¾ ¾ ¾
CH 3 CH 2 Cl ¾ ¾ ¾® (i) ¾ ¾ ¾
¾
¾® (iii), Product (iii) is :
60.
(a) CH 3 CH 2 CH 2 NH 2
(b) CH 3 CH 2 CH 2 CONHCH 3
(c) CH 3 CH 2 CH 2 NHCOCH 3
(d) CH 3 CH 2 CH 2 CONHCOCH 3
O
||
C
–H
O
KMnO 4
H OÅ
¾¾
¾¾® ¾ ¾3 ¾
¾® (G)
H 2O, D
O
Product (G) is :
O
||
C – OH
O
(a)
(b)
O
(c)
61.
HO – CH2
O
||
C–H
CO2H
HO
CO2H
HO
(d) O
HO
Carbonyl compounds can generally be converted to hydrocarbons by :
(a) H 2 Pt
(b) LiAlH 4
(c) N 2 H 4 -KOH/D
(d) K 2 Cr 2 O 7 - H 2 SO 4
62.
Et
(1 ) O 3
¾ ¾ ¾ ¾¾® (A); Product (A) is :
(2) Ag 2O
(3) NaBH 4
(4) H Å
(a)
O
O
O
O
O
(b)
(c)
O
(d)
Et
Et
Et
Et
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410
63.
Which statement about the aldol condensation is correct ?
(a) A Lewis acid is commonly used as a catalyst
(b) The initial step is probably the formation of a carbanion
(c) A Lewis base is employed to induce carbocation formation
(d) The carbon chain is lengthened through the elimination of 1 mole of water
64.
A compound gives a positive test with I 2 NaOH and is extracted from benzene by saturated
NaHSO 3 . It may be :
(a) CH 3 (CH 2 ) 4 CHO
(b) CH 3 (CH 2 ) 3 COCH 3
(c) CH 3 CH 2 COCH 2 CH 3
(d) CH 3 (CH 2 ) 4 CH 2 OH
65.
Which of the following compounds on reaction with excess CH 3 MgBr and subsequent
hydrolysis will give a tertiary alcohol?
(a) C 2 H 5 CHO
(b) C 2 H 5 CO 2 CH 3
(c) C 2 H 5 COOH
(d) CH3CH—CHCH3
O
N ¾ OH
66.
A + B ¾¾¾®
Reactant (A) and (B) is :
(a) Ph ¾ CH 2 ¾ CH == O + NH 2 ¾ OH
O
||
(c) Ph ¾ C ¾ CH 3 + NH 2 ¾ NH 2
67.
(b) Ph ¾ CH == O + NH 2 ¾ OH
O
||
(d) Ph ¾ C ¾ CH 3 + NH 2 ¾ OH
O
||
Ca(OH)2
CH 3 ¾ C ¾ OH ¾¾¾® ( A)
D
Product (A) is :
O
O
(a)
(b)
OH
(c)
68.
(d)
OH
Which of the following does not form a stable hydrate on addition of H2O ?
O
O O O
||
||
||
(a) Ph — C — C — C — Ph
O
(b)
O
O
(c)
O
(d)
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411
69.
Consider the following sequence of reactions.
H
1. C 2H 5MgBr
H 2SO 4 , heat
1. O 3
Ketone A ¾ ¾ ¾ ¾ ¾¾® B ¾ ¾ ¾ ¾ ¾
¾® C ¾ ¾¾®
2. H 2O
- H 2O
+
2. Zn, H 2O
O
O
The ketone (A) is :
(a)
(b)
O
70.
(c)
(d)
O
O
O
In the reaction,
EtONa EtOH
+ CH3COCH3 ¾ ¾ ¾ ¾ ¾
¾® X, the product (X) is :
heat
H3C
H3C
CH3
(a)
(b)
CH3
OH
CH3
(c)
C
(d)
C
CH3
CH3
CH3
71.
The conversion of acetophenone into benzoic acid can be achieved by its reaction with :
(a) sodium hydroxide followed by acidification
(b) iodine and sodium hydroxide, followed by acidification
(c) hydroxylamine followed by reaction with H2SO4
(d) m-chloroperoxobenzoic acid
72.
In which of the following compounds the methylenic hydrogens are the most acidic ?
(a) CH 3 COCH 2 CH 3
(b) CH 3 CH 2 COOC 2 H 5
(c) CH 3 CH 2 CH(COOC 2 H 5 ) 2
(d) CH 3 COCH 2 CN
73.
Which is the major product of the following reaction ?
NH OH
2
¾¾
¾
®
Å
O
H
OH
OH
(a)
(b)
ONH2
NHOH
74.
OH
OEt
(c)
(d)
N
OH
O
||
SOCl 2
H2
Ph ¾ C ¾ OH ¾¾® ( A) ¾¾¾® ( B )
Pd- BaSO 4
Product (B) is :
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412
O
||
(a) Ph ¾ C ¾ H
(b) Ph ¾ CH 2 ¾ OH
(c) Ph ¾ CH 2 ¾ Cl
(d) Ph ¾ CH == CH 2
75.
The presence of unsaturation in organic compounds can be tested with :
(a) Schiff's reagent (b) Tollens' reagent (c) Fehling's reagent (d) Baeyer’s reagent
76.
Which of the following gives iodoform test ?
(a) CH 3 CH 2 OH
(b) C 2 H 5 CHO
(c) (CH 2 OH) 2
77.
Which of the following b-keto carboxylic acid does not undergo decarboxylation on heating ?
(d) None of these
CO2H
(a)
(c)
78.
CO2H O
CO2H
CH3
O
Br
O
(b)
O
(d) None of these
||
PCC
H C == CHMgBr
NH 4Cl H 2O
HOCH 2 CH 2 CH 2 — C — OCH 2 CH 3 ¾ ¾¾®( A) ¾ ¾2 ¾ ¾ ¾¾®( B ) ¾ ¾ ¾
¾¾®(C )
(1 molar equivalent)
KOH
H O
Å
O
||
(CH — C ) O
3 ¾¾
2¾®( D)
¾ ¾¾® ¾ ¾3 ¾
¾® ¾ ¾ ¾
H 2O
Pyridine
Product (D) is :
O
||
O — C — CH 3
O
||
|
(a) H 2 C == CH — CH — CH 2 — CH 2 — C — OH
(b) H 2 C == CH — CH 2 — C — CO 2 H
|
OH
O
O
||
||
(c) H 2 C == CH — C — CH 2 — CH 2 — C — O — C — CH 3
|
OH
O
||
(d) H 2 C == CH — CH 2 — CH — CH 2 — C — O — H
|
OH
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413
79.
The compound shown in the below undergoes racemization on reaction with aqueous acid.
H
OH
O
Which of the following structures best represents the intermediate responsible for this
process?
OH
OH
H
OH
H
OH
(a)
(b)
O
80.
(c)
(d)
OH
OH
HO
OH
The final product of the following sequence of reaction is :
Mg
H 2C == O
H O+
3
(CH 3 O) 2 CHCH 2 CH 2 CH 2 Br ¾¾® ¾¾® ¾¾®
heat
O
||
(a) CH 3 O C CH 2 CH 2 CH 2 CH 2 OH
O
||
(c) H C CH 2 CH 2 CH 2 CH 2 OH
81.
O
||
(b) CH 3 C CH 2 CH 2 CH 2 CH 2 OH
O
O
||
||
(d) H C CH 2 CH 2 CH 2 C H
The amino ketone shown below undergoes a spontaneous cyclization on standing. What is
the major product of this intramolecular reaction ?
O
CCH3
CH2CHNH2
|
CH3
O
(a)
(b)
CH3
CH3
(c)
(d)
NH2
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414
82.
Compound (A) C 6 H 12 O is optically active. Compound (A) give negative Tollens test and
positive test with 2-4-di-nitro phenyl hydrazine. Identify A.
O
O
||
||
(b) CH 3 — C — CH — CH 3
(a) CH 3 — C — CH 2 — CH — CH 3
|
|
CH 3
CH 2 —CH 3
O
O
||
||
(d CH 3 — C — CH 2 — CH 2 — CH 2 — CH 3
(c) H — C — CH 2 — CH — CH 3
|
CH 2 —CH 3
(1) Et O
¾ ¾ ¾2¾® ( A) ; Product (A) of the reaction is :
83.
(2) H 3O Å
99%
O
O
NO2
NO2
(a)
(b)
O
O
NO2
NO2
(c)
(d)
MgBr
84.
O
NH Cl
H 2O
HCl(conc.)
KOH (4 molar)
cold
ethanol, D
4
¾® (O) ¾ ¾ ¾ ¾¾® ( P ) ¾ ¾ ¾ ¾ ¾¾®(Q )
( N) ¾ ¾ ¾
Product (Q) will be :
(a)
85.
(b)
CrO Cl
(c)
(d)
OH
conc.KOH
2 2
Ph — CH 3 ¾ ¾ ¾
¾®( A) ¾ ¾ ¾ ¾
¾® Ph — CH 2 OH + ( B )
Product (B) of above the reaction is :
(a) Ph — CO 2 H
(b) Ph — CO -2
(c) Ph — CHO
(d) Ph — CH 3
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415
CHO
86.
(i) KCN
H
OH
¾¾¾
¾
® Product ; Product obtained in the reaction is :
+
(ii) H
CH2 — OH
D-(+)-Glyceraldehyde
(a) Diastereomer
(c) Meso
O
(b) Racemic
(d) Optically pure enantiomer
H+
NH OH
LAH
2
¾¾¾
¾® ( A) ¾ ¾
¾® ( B ) ¾ ¾¾®(C ); Product (C) of the reaction is :
87.
(a)
(b)
C ºº N
88.
14
(c)
(d)
NaOI
+ CH 3 MgBr ¾¾® ( A) ¾¾® ( B ) + (C )
H Or
3
Product (A) and (C) is :
O
(a)
O
C ¾ CH3 ; CHI 3
14
(b)
C ¾ CH3 ; CHI 3
(d)
CH2 ¾ CHO ; CHI 3
O
(c)
89.
C ¾ CH3 ; CHI 3
14
14
O
OH
||
|
NH 2 ¾ NH ¾ C ¾ NH 2
PCC
Ph ¾ CH ¾ CH 3 ¾¾® ( A) ¾¾¾¾¾¾¾¾® ( B )
Product (B) is :
CH 3
O
||
|
(a) Ph ¾ C == N ¾ C ¾ NH ¾ NH 2
O
||
(c) Ph ¾ CH == N ¾ N ¾ C ¾ NH 2
|
CH 3
O
||
(b) Ph ¾ C == N ¾ NH ¾ C ¾ NH 2
|
CH 3
O
||
(d) Ph ¾ CH == N ¾ C ¾ NH 2
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416
O
2EtOH
90.
¾¾¾®
(P)
r
H
Product (P) is :
(a) Hemiacetal
91.
O
OMe
(b) Acetal
(c) Alcohol
(d) Alkane
; Product of rearrangement is :
(Oxyallyl cation)
O
CH2
(a)
(b)
OMe
OMe
CH2
O
(c)
(d)
OMe
O
OH
Keq
+
92.
R
OMe
HCN
R
CN
C
R
R
Reactant
K eq.
PhCHO
O
a
b
O
||
Ph — C — CH 3
c
O
||
CH 3 — C — H
d
The correct order of decreasing value of K eq. is :
(a) a > b > c > d
(b) d > a > b > c
(c) d > b > a > c
(d) d > a > c > d
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417
93.
Product (B) of the given reaction is :
O
O
O
Me — O — S
+
HO
H+
OH
OMe
(A)
(B)
base
OH
SO2OMe
Me
SO3Me
OMe
(a)
94.
O
O
(b)
O
O
O
(c)
O
(d)
O
O
End product (C ) of the reaction is :
O
O
HO
H+
OEt
O
Ph
(a)
OH
O
Ph
OH
(b)
H OÅ
2 PhMgBr
( A) ¾ ¾ ¾ ¾
¾® ( B ) ¾ ¾3 ¾
¾®(C )
OH
Ph
O
(c)
OEt
Ph
Ph
OH
OH
O
(d)
Ph
does not undergo self aldol condensation
95.
(A)
C11H8O
O3
Ag+
Ph — CHO + 2b ¾¾® oxalic acid
Compound (A) will be :
(a) Ph — C ºº C — C ºº C — CHO
96.
(b) Ph — C ºº C — CH == CH — CHO
(c) Ph — CH == CH — C ºº C — CHO
(d) Ph — CH == CH — C == CH — CO 2 H
O
OH
Product ; Product of the reaction is :
Catalyst TsOH
0°C, 2h
(molecular sieves)
(a)
(c)
O
O
O
O
(62% yield)
O
O
O
O
(b)
(d)
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418
97.
Which pair of reactants compounds may be used to make given acetal ?
O
O
(a)
CH2 — OH
|
CH2 — OH
+
(b)
O
— OH
O
OH
+
(c)
O
— OH
+
OH
+
(d)
OH
OH
O
Å
CHO ¾ H
¾
¾®( B ) ; (A) & (B) are isomers ; Isomer (B) is :
98.
(A)
CH2
O
O
O
(a)
O
(b)
H
OH
O
O
(c)
O
CH2
O
O
(d) H
H
O
OH
OH
OH
99.
PCC
¾¾® ( A)
OH
PCC
¾¾® ( B )
(A) and (B) is differentiated by :
(a) NaH
(b) 2-4 DNA
(c) Tollen’s reagent
(d) NaHSO 3
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419
100.
Which of the following pairs cannot be differentiated by Tollens' reagent ?
(a) Benzaldehyde and benzyl alcohol
(c) 2-Hexanol and 2-hexanone
101.
(b) Hexanal and 2-hexanone
(d) Pentanal and diethyl ether
An optically active compound C 6 H 12 O gives positive test with 2, 4-dinitrophenyl hydrazine,
but negative with Tollens' reagent, what is the structure of the compound ?
O
O
||
||
(a) CH 3 — C — CH 2 — CH 2 — CH 2 — CH 3 (b) H — C — CH — CH 2 — CH 2 — CH 3
|
CH 3
O
||
(c) CH 3 — C — C H — CH 2 — CH 3
|
CH 3
102.
Compound (A) C 6 H 12 O 3 , when treated with I 2 in aqueous sodium hydroxide gives yellow
precipitate. When A is treated with Tollens reagent no reaction occur. When A is hydrolysed
and then treated with Tollens reagent, a silver mirror is formed in test tube. Compound (A)
will be :
O OCH 3
O
||
|| |
(a) CH 3 — C — CH 2 — CH 2 — CH — OH (b) CH 3 —C —C — CH 3
|
|
OCH 3
OCH 3
O
||
(c) CH 3 — C — CH 2 — CH(OCH 3 ) 2
103.
O
||
(d) CH 3 — CH 2 — C — CH — CH 3
|
CH 3
D
O
||
(d) H — C — CH 2 — CH 2 — CH(OCH 3 ) 2
NH — NH
heat
2
2
CH 2 — CH 2 — CO 2 H ¾ ¾ ¾
¾® A ¾ ¾ ¾
¾¾
® B ¾ ¾¾® (C ), Product (C) obtained is :
BaCO 3
KOH
|
CH2 — CH 2 — CO 2H
O
(a) CH 3 — CH == CH — CH 2
(b)
N — NH2
(c)
(d)
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420
104.
Which of following does not react with NaHSO 3 (sodium bisulphite)?
O
O
||
||
(b) CH 3 — C — Et
(a) CH 3 — C — H
O
O
||
||
(d) Ph — CH 2 — C — CH 3
(c) Et — C — Et
CH2 — CH2 — CH2 — NH2
H
2
¾ ¾ ¾¾
® ( A) ; Product (A) is :
105.
Raney Ni
O
(a)
(b)
O
N
H
(c)
(d)
O
N
N
H
H
O
KOH
+CH 2 == CH — CH 2 — Br ¾ ¾¾® ( A) ; Product (A) is :
106.
(75%)
CH2 — CH == CH2
O
O — CH2 — CH == CH2
(a)
O
O
O
O
(b)
O
O
(c)
(d)
CH2 — CH == CH2
CH2 — CH == CH2
CO2H
107.
(1) Me- Li(excess)
I2
(2) HCl H 2O
NaOH
¾¾¾¾¾¾
¾® (A) ¾ ¾ ¾
¾® ( B ) + CHI 3 ; Product ( B ) in this reaction is :
CO2Na
CO2Na
(a)
(b)
CO2Na
CO2Na
(c)
(d)
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421
O
D
108.
D
D
Arrange the following reagent in the correct order in which above transformation is carried
out :
109.
(a) KOD D 2 O ,H + D ,LiAlH 4
(b) H + D , KOD D 2 O ,LiAlH 4
(c) KOD D 2 O , LiAlH 4 , H + D
(d) LiAlH 4 , H + D , KOD D 2 O
O
||
HCN
H OÅ
LiAlH 4
HIO 4
¾®( B ) ¾¾®(C ) ¾ ¾ ¾
¾®( D) ¾ ¾¾
® HCHO + ( E )
CH 3 — C — H ¾ ¾¾®( A) ¾ ¾3 ¾
D
Compound (C)can show geometrical isomerism. Product (E) of the reaction will be :
O
O
||
||
(b) CH 3 — CH 2 — C — H
(a) CH 3 — C — CH 3
(c) CH 3 — CHO
110.
(d) HCHO
Arrange in their increasing order of equilibrium constants for hydration ?
O
O
O
O
||
||
||
||
CH 3 — C — CH 2 — Cl, H — C — H,
CH 3 — C — H,
CH 3 — C — CH 3 ,
(A)
(C )
(B)
(D)
O
||
Cl — CH 2 — C — H
(E )
(a) A < B < C < D < E
(c) A < C < E < B < D
111.
(b) A < C < B < E < D
(d) C < A < B < E < D
End products of the following sequence of reactions are :
O
1. I + NaOH, D
¾ ¾2¾ ¾ ¾
¾®
C — CH3
2. H +
3. D
O
O
(a) yellow ppt. of CHI 3 ,
O
(b) yellow ppt. of CHI 3 ,
COOH
CHO
O
(c) yellow ppt. of CHI 3 ,
(d) yellow ppt. of CHI 3 ,
COOH
COOH
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422
112.
(1) EtONa
Ph — CH 2 — CN ¾ ¾ ¾ ¾ ¾
¾
¾® (P) ; Product (P) of the reaction will be :
O
||
(2)CH 3 —C —Cl
(3) H 3O Å D
O
||
(a) Ph — CH 2 — C — H
O
||
(b) Ph — CH 2 — C — CH 3
O
||
(c) Ph — CH — C — H
|
CH 3
O
O
||
(d) Ph — CH — C — CH 3
|
CH 3
(i) NaCN
113.
C — H ¾ ¾ ¾¾® Products. Products of the reaction are :
(ii) H 2SO 4
(a)
(b)
(c)
(d)
Racemic mixture
Diastereomers
Meso
Mixture of meso compound and optically active compound
HgSO 4
LiAlH 4
114. ( A) ¾¾¾¾® ( B ) ¾¾¾®
dil. H 2SO 4
(C )
recemic mixture
\ reactant (A) is :
(a) CH 3 ¾ C ºº CH
(c) CH 3 ¾ C ºº C ¾ CH 3
115.
(b) HC ºº CH
(d) Ph ¾ CH == CH 2
O
||
NaNO 2
® ; Major product of this reaction is :
CH 3 CH 2 — C — CH 3 ¾ ¾ ¾¾
HCl
O
||
(a) CH 3 CH — C — CH 3
|
NO
O
||
(c) CH 3 — C — C — CH 3
||
N—OH
O
||
(b) CH 3 — CH 2 — C — CH == N — OH
(d) CH 3 — CH 2 — C — CH 3
||
N—OH
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423
O
(1) NH 2OH
¾ ¾ ¾+ ¾
¾®( A) + ( B ). Product (A) & (B) are :
116.
( 2) H , D
( 3) LiAlH 4
H
N
(a)
&
(b)
N—H
&
OH
NH
(c)
OH
NH
&
NaOH
117.
(d)
HCl
D
&
+ CH 3 NO 2 ¾ ¾ ¾
¾® A ¾ ¾
¾® ( B ). Product (B) is :
nitromethane
93%
CH == CH — NO2
(a) HO
(b)
OH
CH == CH — NO2
(c)
(d)
HO
O
(1) HCN
¾ ¾ ¾ ¾ ¾¾® ( A) . Product (A) is :
118.
(2) LiAlH 4
(3) NaNO 2 H +
major
O
O
(a)
(b)
(c)
(d)
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O
119.
Cl
KOH
Cl ¾ alc.
¾ ¾¾® ( A). Product (A) is :
(2 mole)
O
O
(a)
C
(b)
O
O
(d) HO
(c)
120.
O
||
R — C— R
OH
OH
|
R —C—R
|
CN
HCN
(catalyst)
Which of following can be used as a catalyst in the above reaction?
O
||
(d) HSO -4
(a) Cl (b) CH 3 — C — O - (c) Et — O 121.
Arrange the following carbonyl compounds in decreasing order of their reactivity in
nucleophilic addition reaciton.
CHO
CHO
(i)
NO2
(ii)
(a) ii > iii > i > iv
(c) iii > ii > i > iv
122.
COCH3
CHO
CH3
(iii)
(iv)
(b) ii > i > iv > iii
(d) iii > i > iv > ii
The following reaction were carried out.
H
O
I NaHCO
2
3
¾¾
¾ ¾¾
®
OH
The final product formed in the above reaction sequence is :
H
O
(a)
ONa
(b)
O
I
I
O
I
H
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H
H
I
O
(c)
O
(d)
ONa
OH
I
O
123.
I
O
58%
Me3C — C — CH3
(A)
Me3C — C — CH2 — Br
(B) 54%
OH
O
Me3C — CH — CH2
A.
68%
(C)
Yield of each step as actually carried out in the laboratory is given above. What is overall
yield of reaction?
(a) 42%
(c) 21%
B.
Me3C — CH — CH2 — Br
(b) 31%
(d) 60%
What is the appropriate reagent to carry out above synthesis, i . e. , A, B, C respectively are :
(a) Br 2 H + , LiAlH 4 ,H Å
(b) Br 2 H + ,NaBH 4 ,HO -
(c) NBS, AlCl 3 ,HO -
(d) Br 2 HO - ,BF3 ,HO -
OH
Ni
3H 2
(High temp
& pressure)
Cu
HÅ
NH OH
HO -
2
¾ ¾ ¾ ¾¾®( A) ¾ ¾®( B ) ¾ ¾ ¾
¾®(C ) ¾ ¾
¾®( D) ¾ ¾¾®( E ) ;
124.
Product (E) is :
(a) Nylon 66
125.
(b) Nylon 6
(c) Styrene
(d) Polystyrene
Methyl vinyl ketone on reaction with LiCuMe 2 gives a major product, whose structure is :
Me
(a) Me
Me
(b)
Me
O
HO
O
(c)
Me
Me
(d)
Me
HO
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126.
Which of following is in capable to show iodoform test ?
O
OH
|
CH3
(a)
(b) Ph — CH == CH — CH — CH 3
OH
H2C == CH
CH3
O
H
(c)
CH2 — C — CH3
(d)
D
127.
O
O
||
||
(NH 4 )2CO 3
CCl 3CO 2Na
CH 3 — C — CH 2 — CH 2 — C — CH 3 ¾¾¾¾® (A)¾¾¾¾®
D
D
( B)
(major)
Product (B) of above reaction is :
(a)
(b)
(c)
(d)
O
CO2Et
H 3O +
A ; Product obtained is :
¾¾¾®
D
128.
EtO2C
O
O
OH
O
CO2Et
(a)
(b)
(c)
(d) None of these
O
O
129.
( A)
Symmetrical
Ketone
O
LiAlH 4
Hr
¾¾¾® ( B ) ¾®
D Diastereomers
Reactent (A) is :
O
||
(a) CH 3 ¾ C ¾ CH 3
O
||
(b) CH 3 ¾ C ¾ CH 2 ¾ CH 3
O
||
(c) CH 3 ¾ CH 2 ¾ C ¾ CH 2 ¾ CH 3
(d) CH 3 ¾ CH 2 ¾ CH 2 ¾ CH == O
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427
130.
H OÅ
ether
+ Li + and Al 3+ Salt
+ x LiAlH 4 ¾ ¾¾® ¾ ¾3 ¾
¾®
4
Value of x in above reaction is :
(a) 1
(b) 2
(c) 3
(d) 4
Å
®
H SO 4
H O
CHCl 3
2OH
131. ( A) ¾ NH
¾¾
¾®( B ) ¾ ¾2 ¾
¾®(C ) ¾ ¾3 ¾
¾®( D) + ( E ) ¾ ¾ ¾
¾® CH 3 — N == C
KOH, D
D
SOCl
HÅ
(i) PhMgBr(excess)
CH I
Zn Cu
2
2
( D) ¾ ¾ ¾
®( F ) ¾ ¾ ¾ ¾ ¾ ¾¾®(G) ¾ ¾
¾®( H ) ¾ ¾2¾
®
(ii) H
Å
D
Molecular weight of compound (A) is :
(a) 58
(c) 60
(b) 120
(d) 182
O
132.
||
aqueous acid
Ph 2 CH — C — H ¾ ¾ ¾ ¾ ¾
¾® ( A) + enol + aldehyde
81%
2%
17%
Product (A) of above reaction will be :
OH
|
(b) Ph 2 CH — CH 2
(a) Ph — C == CH — O
|
Ph
OH
|
(c) Ph 2 CH — CH — OH
133.
134.
O
||
(d) Ph 2 CH — C — CH 3
Which of the following will form stable hydrate ?
(a) CCl 3 CHO (Chloral)
(b)
(c) (CF3 ) 2 CO
(d) All of these
(Ninhydrin)
The pH at which maximum hydrate is present in an solution of oxaloacetic acid:
O
O
O
||
||
||
H — O — C — C — CH 2 — C — O — H
pK a = 2.2
(a) pH = 0
(c) pH = 4
pK a = 3.98
(b) pH = 12
(d) pH = 6
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135.
Arrange their stabilities of given gem- diols in decreasing order.
OH
OH
OH
OH
(I)
(II)
(III)
OH
OH
(a) I > II > III
136.
137.
(b) III > II > I
Maximum hydration takes place of :
O
O
||
||
(b) CH 3 C CH 3
(a) CF3 C CF3
(c) I > III > II
(d) III > I > II
O
||
(c) CH 3 CH - C CH 3
|
Cl
O
||
(d) C 6 H 5 C C 6 H 5
The conversion, PhCN ® PhCOCH 3 , can be achieved most conveniently by reaction with:
(a)
(b)
(c)
(d)
CH 3 MgBr followed by hydrolysis
I 2 — NaOH, CH 3 I
dil. H 2 SO 4 followed by reaction with CH 2 N 2
LAH followed by reaction with CH 3 I
O
D
138.
H–O
O
(A)
Zn(Hg)/HCl
(B)
In the above reaction, product (B) is:
(a)
(b)
(c)
(d)
OH
Hr
LiAlH 4
139. ( A) ¾¾¾® ( B ) ¾®
D
Structure of A is :
O
O
(a)
(b)
O
(c)
O
(d)
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140.
O
O3
HCHO+(A)
Ph – NH2
(B)
O
Product (B) is :
O
O
||
||
(a) Ph — NH — C — CO 2 H
(b) Ph — NH — C — CH 2 — CO 2 H
(c) O
(d) O
N – Ph
O
N
O
Ph
CO2H
141.
To carry out above conversion, arrange the following reagents in correct order.
O 3 Zn
EtONa / EtOH D
(3)
( 2)
(1)
142.
NaOCl
(a) 1 ® 3 ® 2 ® 4
(b) 1 ® 2 ® 4 ® 3
(c) 1 ® 3 ® 4 ® 2
(d) 1 ® 2 ® 3 ® 4
H+
( 4)
HOCH 2
O
||
|
O3
CH -C -CH 3
¾ ¾3¾ ¾ ¾
¾® ( A) ¾ ¾ ¾¾
® ( B ) + HCHO
H 2 C = CH - CH 2 - CH 2 - C - OH
(CH 3 )2S
TsOH
|
CH 2 - CH 3
Product (B) is:
CH3
O
CH2
O
C
(a) H — C — CH2 — CH2 — C
O
CH3
Et
O
O
CH3
C
(b) H — C — CH2 — CH2 — C
CH3
Et
O
O
CH2
(c) H — O — C — CH2 — CH2 — C
CH3
O
O
C
CH3
Et
O
O
CH3
C
(d) H — C — CH2 — C
CH3
Et
O
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430
O
Br
C—H
CHO
CHO
a
143.
b
Identify appropriate reagents for the above reaction:
(a) a = Br 2 CCl 4 ,
b = aq.KOH
+
b = aq. KOH
+
(c) a = Br 2 H ,
b = alc.KOH
(d) a = Br 2 HO - ,
b = aq.KOH
(b) a = Br 2 H ,
OH
OH
PhCHO
144.
¾ ¾ ¾¾® ( X ) ; Product (X) of this reaction is :
H+
Me
96%
Me
Ph
Ph
CH
CH
O O
(a)
(b)
O
(c)
145.
(d)
The K eq. values in HCN addition to following aldehydes are in the order :
O
O
O
H
H
Me2N
MeO
(I)
(a) I > II > III
OH
146.
H
(1) CH3—C—CN
(II)
(b) II > III > I
K1
(III)
(c) III > I > II
(d) II > I > III
(c) K 2 > K 1
(d) K 1 = K 2 = 1
O
+HCN
CH3
OH
(2) CH3—C—CN
K2
O
+HCN
H
elation between K 1 and K 2 is :
(a) K 1 = K 2
H
(b) K 1 > K 2
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147.
Which of the following is correct for the reaction ?
O
pH = 9 to 10
+ HCN ¾ ¾ ¾ ¾
¾® ( A)
(a)
(b)
(c)
(d)
148.
A is cyanohydrin
Nucleophilic-addition reaction
The above reaction is not shown by alkenes
All of these
Which of the following compounds (i through v) should not be classified as an acetal ?
H
OCH3
CH3O
O
O
O
CH3
O
(i)
149.
O
O
O
O
(ii)
(iii)
(v)
(iv)
(a) ii and iii
(b) iv
(c) i
(d) none (they are all acetals)
In which of reactions final product is NOT a ketone :
CH – I
HgSO
4
2
(a) CH 3 — C ºº C — H ¾ NaNH
¾ ¾¾
® ( A) ¾ ¾3¾
¾® ( B ) ¾ ¾ ¾
¾
® (C )
H 2SO 4
CH — CH – I
Hg (OAc ) , H 2O
2
(b) H — C ºº C — H ¾ NaNH
¾ ¾¾
® (C ) ¾ ¾3¾ ¾ 2¾
¾® ( D) ¾ ¾ ¾ ¾2¾¾
®(E)
NaBH 4 , H -
O
||
CH – I
(c) R — C — OH ¾ NaOH
¾¾
¾® ( A) ¾ ¾3¾
¾® ( B )
NaNH 2
(1) BH 3 ×THF
( 2) H 2O 2 / HOs
CH 3 – I
(d) 1-butyne ¾ ¾ ¾
¾® ( A) ¾ ¾ ¾
¾® ( B ) ¾ ¾ ¾ ¾ ¾ ¾® (C )
150.
151.
The reaction of ethyl methyl ketone with Cl 2 /excess OH – gives the following major product
(a) ClCH 2 CH 2 COCH 3
(b) CH 3 CH 2 COCCl 3
(c) ClCH 2 CH 2 COCH 2 Cl
(d) CH 3 CCl 2 COCH 2 Cl
The product obtained from the following sequence of reactions is
HgSO
NaBH
4
4
CH 3 — C º CH ¾ ¾ ¾
¾
® A ¾¾¾
¾
®B
H 2SO 4
(a) propanol
(b) 2-propanol
(c) 1-propanol
(d) propanhe
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152.
Which of the following shows oxidation of reactant.
O
O
(1)
O
(2)
OCH3
(4) CH2 == CH2 ¾® CH3—CH2—Cl
(3)
(a)
153.
1
(b)
1, 2
(c)
1, 2, 3 (d)
All of the above
The enolate ion that reacts with
O
to form
O
O
O
O
(a)
O
(b)
(c)
(d)
O
O
O
154. CH3—C—CH3
NaNH2
HCºCH
P
Q
H3O
+
R
1H2/Pd
What is the final product T.
O
(a) H3C—C == C—C—CH3
CH3
S
Al2O3
D
T
OH
(b)
CH3—C—CH3
H2C == CH
CH3
(c) CH3—C == CH—CH3
O
CH3
(d) CH3 == C—CH == CH2
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ANSWERS — LEVEL 1
1.
(a)
2.
(b)
3.
(d)
4.
(c)
5.
(a)
6.
(c)
7.
(b)
8.
(b)
9.
(b)
10.
(c)
11.
(c)
12.
(c)
13.
(b)
14.
(b)
15.
(b)
16.
(b)
17.
(b)
18.
(b)
19.
(b)
20.
(d)
21.
(b)
22.
(b)
23.
(b)
24.
(d)
25.
(c)
26.
(b)
27.
(b)
28.
(a)
29.
(b)
30.
(c)
31.
(d)
32.
(c)
33.
(b)
34.
(b)
35.
(a)
36.
(b)
37.
(c)
38.
(d)
39.
(b)
40.
(a)
41.
(b)
42.
(a)
43.
(a)
44.
(b)
45.
(b)
46.
(a)
47.
(b)
48.
(d)
49.
(c)
50.
(b)
51.
(d)
52.
(b)
53.
(b)
54.
(c)
55.
(b)
56.
(b)
57.
(a)
58.
(d)
59.
(c)
60.
(c)
61.
(c)
62.
(a)
63.
(b)
64.
(b)
65.
(b)
66.
(d)
67.
(b)
68.
(d)
69.
(b)
70.
(c)
71.
(b)
72.
(d)
73.
(d)
74.
(a)
75.
(d)
76.
(a)
77.
(a)
78.
(a)
79.
(c)
80.
(c)
81.
(d)
82.
(b)
83.
(b)
84.
(b)
85.
(b)
86.
(a)
87.
(b)
88.
(c)
89.
(b)
90.
(b)
91.
(c)
92.
(b)
93.
(b)
94.
(b)
95.
(c)
96.
(c)
97.
(d)
98.
(b)
99.
(c)
100.
(c)
101.
(c)
102.
(c)
103.
(c)
104.
(c)
105.
(c)
106. (b)
107.
(a)
108.
(c)
109.
(c)
110. (b)
111.
(c)
112. (b)
113. (b)
114.
115.
(c)
116.
(a)
117.
(a)
118.
(a)
119. (b)
120.
(c)
121. (b)
122. (b)
123. A-c
123. B-b
124. (b)
125.
(a)
126.
(c)
127.
(a)
128. (b)
129.
(c)
130.
131.
132.
(c)
133. (d)
134.
(a)
135.
(a)
136.
137.
(a)
138. (b)
139. (d)
140. (b)
141. (d)
142.
(a)
143.
(c)
144. (b)
145. (d)
146. (b)
147. (d)
148. (d)
149.
150. (b)
152. (b)
153.
154. (d)
(a)
(c)
(c)
(a)
(a)
(c)
151. (b)
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434
Level - 2
1.
Select the best choice for example (A to L) from the examples (a to n) given below. Write
your choice in the box given.
A.
An acetal derivative of a ketone.
B.
A chiral ketone.
C.
An aldehyde that gives a aldol condensation with itself.
D.
An oxime derivative
E.
A reagent that reduces aldehydes to 1°- alcohols.
F.
An a, b-unsaturated ketone.
G.
A reagent that oxidizes aldehydes to carboxylic acids.
H.
A reagent that reduces ketones to alkanes.
I.
An enamine derivative of a ketone.
J.
An intermediate in imine formation.
K.
A cyclic hemiacetal.
L.
A cyanohydrin derivative.
CH3
(a)
O
OH
(b)
(c)
CN
(d)
OH
R
NHR'
H
OH
(e)
O CH3
(f)
Zn(Hg)H 3O (+ )
O
O
(g)
(h)
NaBH 4 aq. alcohol
HO
(j)
Ag(NH 3 ) 2
(+ )
OH (- )
(k)
(i)
H
OCH3
N
CH3
(l)
CH3
C
OCH3
CH3
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435
O
N
(m)
(n)
CH3
CH2
C
H
2.
The following questions refer to the compounds (A to G) shown below :
Which compounds are
Which compounds are
Which compound are
reduced by sodium ii. hydrolyzed
by
hot iii. oxidisized
by
borohydride ?
aqueous acid ?
CrO 3 pyridine?
i.
A
B
C
D
E
F
G
H
A
B
C
D
E
F
G
H
A
B
C
D
E
F
G
H
O
O
A.
H
B.
O
O
C.
D.
O
O
O
E.
O
F.
HO
3.
O
H
G.
O
H.
O
Match the column:
Column (I)
(a)
O
LiAlH 4
¾¾¾®
Column (II)
(p) racemic mixture
O
(b)
(1) KCN
¾¾¾®
r
(q) Diastereomers
(2) H
KCN
(c) Ph ¾ CH ¾ Cl ¾¾®
2
(r) Nu-addition reaction
O
(d)
(1) CH 3 MgBr
¾¾¾¾¾®
r
(s) Nu-Substitutions reaction
(2) H
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4.
Complete the following table.
REAGENT(S)/
CONDITIONS
MAJOR ORGANIC
PRODUCTS
H 2 Pd - C in ethanol
(solvent)
A
H + H 2O D
B
REACTANT
O
CH3
a.
COOCH3
b.
COOCH3
O
H
c.
O
–
+
C
(CH 3 ) 2 C— P(C 6 H 5 ) 3
1. Li + [(CH 3 ) 2 Cu]-
d.
D
in dry ether
2. H + H 2O
CH3
e.
OH - ethanol D
E
O
CH3
5. Comprehension
Consider the following reactions and answer A and B.
O
(CH3)3 C
C
O
58%
CH3 ¾¾®
(CH3)3 C
(a)
C
CH2
54%
(b)
Br ¾¾®
OH
(CH3)3 C
C
O
CH2
68%
Br ¾¾® (CH3)3 C
H
A.
C
CH2
H
Suggest a reagent appropriate step (a) the synthesis.
(a) HO - Br 2 (1mole)
(b) H + Br 2 (1 mole)
(c) both (a) and (b)
(d) None of these
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B.
Yield of each step as actually carried out in laboratory is given above each arrow. What is
overall yield of the reaction ?
(a) 60%
(b) 21%
(c) 40%
(d) 68%
6.
O
C—H
Reaction 1.
2O, AcONa, D
¾(1)Ac
¾¾¾¾¾
¾® ( A)
Å
(2)H 3O , D
Reaction 2.
O
||
2 )3
¾¾¾¾
¾® ( B )
Ph — CH == CH — C — CH 3 ¾ Al(OCHMe
CH 3— CH — OH
|
CH 3
Reaction 3.
OH
|
Ph — CH == CH — CH — CH 3 ¾(1)NaOI
¾¾Å¾® (C )
(2)H
Degree of unsaturation present in compound (A + B + C) is ?
7.
Within each set, which compound should be more reactive toward carbonyl addition
reaction ?
A
B
Set (1)
O
||
CH 3 — C — CH 2 — Br
O
||
CH 3 — C — CH 2 — CH 2 — Br
Set (2)
O O
|| ||
CH 3 — C — C — CH 3
O
||
CH 3 — C — CH 2 — CH 3
Set (3)
CH 3O
CH == O
Set (4)
O
||
C—H
Set (5)
O
O 2N
CH == O
O
||
CH 3 — C — H
O
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CHO
Set (6)
N
|
H
N
|
H
CHO
O
O
O
C—H
Set (7)
O
O
C—H
O
CHO
Cl
CHO
Set (8)
Set (9)
C
O
||
C—H
O
||
CH 3 — C — CH 2 — CH 3
Set (10)
8.
O
O
||
C — CH 3
Match the Column (I) and Column (II). (Matrix)
Column (I)
Column (II)
O
(A)
HCN
4
2
¾ traces
¾¾¾¾
¾®( A) ¾ LiAlH
¾¾
¾
®( B ) ¾ NaNO
¾¾
¾
®(C ) (p)
of KOH
HCl
Formation of six member
ring takes place
O
(B)
+
2OH
¾ NH
¾¾
¾® ( A) ¾ H¾
¾® ( B ) ¾ LAH
¾¾®(C )
(q)
Final product is Ketone
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(C)
O
O
||
||
–
¾¾® ( A)
CH 3 - C - CH 2 - CH 2 - CH 2 - C - H ¾ HO
D
Ph
Å
¾ H¾
¾® ( A)
CH3
D
(D)
OH OH
9.
Final product formed will
react with 2,4-DNP.
(s)
(2,4-di-nitrophenyl
hydrazine)
Consider reactions A through F. Those carbon atoms undergoing change, as part of a
functional group, are marked as C 12 , C 14 or starred. In the cases shown, each carbon atom
has either been reduced or oxidized. Your job is to identify the change in oxidation state that
has occurred for each of the marked carbon.
Reaction
Br2
¾® CH 3CHBrCH 2Br
A. CH 3 CH == CH 2 ¾ ¾
12
B.
14
(i)B2 H 6
CH 3 CH == CH 2 ¾(ii)H
¾¾¾¾
¾® CH 3CH 2CH 2OH
O ,NaOH
12
C.
14
2
2
*
4
CH 3CH 2 C H == O ¾ NaBH
¾¾
¾
® CH 3CH 2CH 2OH
(+ )
Ag
*
D. CH CH C
¾¾¾
¾® CH 3CH 2CO 2H
3
2 H == O ¾ H
O, pH > 8
2
E.
CH 3COCH 3
CH 3CO C H 2 C O 2H ¾ Heat
¾¾® +
12
14
O == C == O
tautomerization
F. H 2 C == C(OH)C 2H 5 ¾ ¾¾¾¾¾® H 3CCOC 2H 5
12
10.
(r) Final product formed will
give positive Tollens test
14
C 12
C 14
Reduced
Reduced
Oxidized
Oxidized
Reduced
Reduced
Oxidized
Oxidized
Reduced
Oxidized
Reduced
Oxidized
Reduced
Reduced
Oxidized
Oxidized
Reduced
Reduced
Oxidized
Oxidized
Consider the possible formation of an aldehyde or ketone product when each of the ten
compounds in the column on the left is treated with each of the reagents shown in the top
row. Check the designated answer box if you believe an aldehyde or ketone will be formed.
Assume that the reagents may be present in excess. For each checked reaction, try to draw
the structure of the major product (s).
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(i) BH3 in THF
(ii) H2O2 + NaOH
r
H3O
Pb(OAc)4
[or HIO4]
Starting
Jone's Reagent
CrO3 in aq. acid
PCC
C5H5NHCrO3Cl
440
OH
CH3
C
CH3
CH3
C
CH3
CH2
OH
CH3
CH3
OH
CH3
CH3
CH3
OH
CH3
CH3
H3C
C=C
H3C
CH3
CH3
HO
OH
HO
C2H5
CH3
OH
CH3
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11. Comprehension
Wittig reaction :
The reaction of a phosphorus ylide with an aldehyde (or) ketnoe introduces a carbon-carbon
double bond is place of the carbonyl bond.
CH 2
O
||
||
R — C — R + Ph 3 P == CH 2 ¾® R — C — R + Ph 3 P == O
Mechanism :
O
||
R–C–R +
Q
Q
Å
¾®
CH2 – PPh3
(Nucleophilic addition
reaction)
Å
PPh3
O
|
|
R — C — CH 2
|
R
(betaine intermediate)
CH 2
||
O == PPh 3 + R — C — R
¬¾
­
¯
O — PPh3
|
|
R — C — CH 2
|
R
(oxaphosphetane
intermediate)
Driving force of the reaction is high bond energy of (P == O) . (DH = –ve)
O
A.
+ Ph 3 P == CH 2 ¾® (A) (major), Major product (A) is :
CH2
CH3
(a)
(b)
CH3
CH – CH 3
(c)
(d)
O
||
Å
- Li
B. CH 3 — C — CH 2 — CH 2 — CH 2 — CH 2 — PPh 3 ¾ Ph
¾¾® ( A) , Major product (A) is :
D
CH3
CH2
(a)
(b)
CH3
(c)
(d)
H
H
C. CH
3
Ph 3 P
CH3 ¾ ¾¾® (A) , Major product (A) is :
O
(a) cis-2-butene
(b) trans-2-butene
(c) iso-butene
(d) 1-butene
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D.
O
O
O
||
||
||
NaH
CH 3 - C -(CH 2 ) 3 - C - CH 2 - P (OEt) 2 ¾ ¾¾® ( A) (cyclic). Product (A) is :
O
O
O
CH3
(a)
(b)
(c)
(d)
O
CH3
CH3
E. Identify major product in given intramolecular Wittig reaction :
O
||
Rxn.-1 ¾®
CH 3 — C — CH 2 — CH(CO 2 Et) 2 + H 2 C == CH —
Å
NaH
PPh 3 ¾ ¾¾® ( A)
CH = O
Rxn.-2 ¾®
Q Å
+ H 2 C == CH —
Å
PPh 3 ¾¾® ( B )
ONa
Product (A) and (B) respectively are :
(a)
(b)
CO2Et
CH3
&
CO2Et
O
CO2Et
&
CO2Et
O
CO2Et
(c)
CO2Et
&
O
(d)
CO2Et
&
CO2Et
CH2 – Br
(1) Ph 3 P (2 mole)
¾ ¾¾¾¾® (A) ; product (A) is :
F.
CH2 – Br
(a)
(2) 2Ph - Li
(3) CHO
|
CHO
(b)
(c)
(d)
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12. Match the column :
Column (I)
Column (II)
Conversion
Reagent
O
CH3
¾®
Å
(a) Me N
3
(p)
NH 2 NH 2 HO Q , D
(Wolff- Kishner reduction)
Å
Me3N
O
(b)
O
Zn(Hg), HCl
(Clemmensen reduction)
OH
O
(c)
(q)
¾® O
O
¾®
(r)
LiAlH 4
(s)
None
HO
OH
(d)
O
OH
¾®
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13. Comprehension
HgSO 4
(1) NaBH
4
( A) ¾¾¾® ( B ) ¾¾¾¾®
CH 3 ¾ C ¾ CH 2 ¾ CH 3
r
dil. H 2SO 4
( 2) H / D
||
CH ¾ CH 3
A.
B.
Reactant (A) is :
(a) CH 3 ¾ C ºº C ¾ CH ¾ CH 3
|
CH 3
(b) HC ºº C ¾ C ¾ C ¾ C
|
C¾C
(c) CH 3 ¾ CH ¾ C ºº CH
|
CH 2 ¾ CH 3
(d) CH 3 ¾ C ºº C ¾ CH 2 ¾ CH 2 ¾ CH 3
Product (B) is :
O
(a)
O
(b)
O
O
(c)
(d)
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ANSWERS — LEVEL 2
1.
A – l; B – g; C – n; D – k; E – h; F – c; G – j; H – f; I – m; J – d; K – e; L – b
2.
i – A, B, C, E, F; ii – D, G, H; iii – B, E, F
3.
a - p,r; b - r; c - s; d - p, r
OH
|
B : Ph — CH 2 — COOH;
A : Ph — CH — CH 3 ;
4.
CH 3
C : Ph — CH == C /
;
\ CH
3
O
O
CH2 — C — CH3
D:
;
CH3
E:
CH2 — C — CH3
O
5.
A – b; B – b
6.
A + B + C = 17
7.
set 1 – A; set 2 – A; set 3 – B; set 4 – B; set 5 – A; set 6 – B; set 7 – B;
set 8 – B; set 9 – A; set 10 – B
8.
A – p, q, s; B – p; C – p, q, s; D – p, q, s
9.
A : both are oxidized; B : C 12 is reduced, C 14 is oxidized; C : reduced; D : oxidized
E : C 12 is reduced, C 14 is oxidized; F : C 12 is reduced, C 14 is oxidized
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+
H3O
(i) BH3 in THF
(ii) H2O2 + NaOH
✓
✓
✗
✗
✗
✗
✗
✗
✗
✓
✓
✓
✓
✓
✗
✓
✗
✗
✗
✗
✗
✓
✗
✗
✓
✓
✗
✓
✓
✓
✗
✗
✗
✗
✗
✗
✗
✗
✗
✓
✓
✓
✗
✗
✗
✓
✓
✓
✓
✓
✗
✗
✗
✗
✓
✓
✓
✗
✗
✗
Pb(OAc)4
[or HIO4]
Jone's Reagent
CrO3 in aq. acid
Compound
PCC
C5H5NHCrO3Cl
10.
OH
CH3
C
CH3
CH3
C
CH3
CH2
OH
CH3
CH3
OH
CH3
CH3
CH3
OH
CH3
CH3
H3C
C=C
H3C
CH3
CH3
HO
OH
HO
C2H5
CH3
OH
CH3
11.
A – a; B – a; C – b; D – b; E – a; F – b
12.
a – q; b – s; c – r; d – p
13. A. (c) B. (d)
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8
ALDOL AND CANNIZARO REACTION
Level - 1
1.
Compound A and B, both were treated with NaOH, producing a single compound C.
O
O
CH3
CH3
+
HO -
¾ ¾¾® C. Compound (C) is :
heat
OH
(A)
OH
(B)
O
O
(a)
C — CH3
(b)
O
O
(c)
O
(d)
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O
O
C — CH3
?
2.
(a)
(b)
(c)
(d)
3.
; This conversion can be achieved by :
CH3
CH3
OH
Dehydration, Hydrolysis
Retro aldol and further condensation
Perkin condensation & Clemmensen reduction
Clemmensen and Perkin condensation
This is an example of an intramolecular aldol reaction :
O
H SO
2
4
¾ ¾¾
¾
® (A); Product (A) is :
H 2O
O
O
(a)
4.
O
O
(b)
O
(c)
O
O
||
||
CH 3 — C — CH 2 — CH 2 — CH 2 — CH 2 — C — H
(d)
HO - /D
¾ ¾¾¾® ( A) ; Product (A) is :
(73%)
O
O
O
C ¾ CH3
C ¾ CH3
CH3
(a)
(b)
(c)
(d)
CHO
5.
base
Ph — CH == CHCHO + CH 3 CH == CHCHO ¾ ¾¾®( A) 87% ; Product of this reaction is :
EtOH, D
(a) Ph — (CH == CH) 2 — CHO
(c) Ph — (CH == CH) 4 CHO
6.
(b) Ph — (CH == CH) 3CHO
(d) Ph — CH == CH — CH == CH — CH 3
10% NaOH
H2
CH 3 CHO ¾ ¾¾¾¾® ¾¾® ¾ ¾
¾® (A) ; Product (A) of the reaction is :
5°C
(a) propanol
D
Ni
(b) ethanol
(c) butanol
(d) pentanol
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O
||
C – CH3
7.
NaOH
(A) ¾ ¾¾
¾®
. Reactant (A) is :
D
O
O
||
O
||
(a) CH 3 - C - (CH 2 ) 5 - C - CH 3
O
||
(b) CH 3 - C - (CH 2 ) 4 - C - H
O
O
||
O
||
||
||
(d) CH 3 - C - (CH 2 ) 4 - CH 2 - OH
(c) H - C - (CH 2 ) 5 - C - H
CH 3
|
KOH, H 2O
® ( A); Product A is:
CH 3 - C - CH 2 - C - CHO ¾ ¾¾¾¾
|
CH 3
O
||
8.
O
O
O
(a)
(b)
O
(c)
(d)
O
||
LDA
¾ ¾¾® ( A) ; Product A is:
9.
CH 3 -CH 2 -I (major)
O
||
O
||
(a)
10.
(b)
O
||
O
||
(c)
(d)
The reaction ,
CHO
heat
+ conc. NaOH ¾ ¾
¾® , products Identify the product.
CHO
CH(OH)2
(a)
(b)
O
CH(OH)2
COO¯
CH2OH
(c)
(d)
COO¯
COO¯
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Compare enolate A with enolate B.
O
O
:
:
11.
O
O
B
A
Which of the following statements is true ?
(a) A is more stable than B
(c) B is more stable than A
12.
(b) A and B have the same stability
(d) No comparison of stability can be made
Benzalacetone is the product of mixed aldol condensation between benzaldehyde
(C 6 H 5 CH = O) and acetone [(CH 3 ) 2 C = O]. What is its structure ?
O
||
(a) C 6 H 5 CH = CHC CH 3
O
(b) C 6 H 5 CH = C(CH 3 ) 2
O
(c) C 6 H 5 C CH = CHCH 3
(d) C 6 H 5 CH 2 C CH = CH 2
||
13.
||
||
Identify the major product P in the following reaction:
O
O
O
aq. NaOH
||
¾ ¾¾¾
¾® P
Cl
+
H
O
||
O
(a)
(b)
O
(c)
O
(d)
O
O
||
O
O
OH
dil. NaOH
PCC
¾¾¾®
(A) ¾¾¾¾®
(B)
D
14.
Product ( B ) is:
O
(a)
(b)
O
O
O
(c)
(d)
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O
15.
C — CH 3
(i)O 3
NaOH
( A) ¾ ¾¾¾¾® ( B ) ¾ ¾¾
¾®
(ii)Zn, H 2O
D
the reactant (A) will be :
CH2
(a)
16.
(b)
(c)
(d)
Identify the principal product of the following reaction?
CH2CH == O
NaOH
¾ ¾¾¾¾¾¾¾® H 2 O + ?
ethanol, water, heat
CH2CH == O
CH == O
CH == O
(a)
(b)
CH == O
OH
O
(c)
(d)
OH
17.
18.
O
Which one of the following compounds is the best choice for being prepared by an efficient
mixed aldol addition reaction?
OH O
O
||
|
||
(a)
(b)
CCH2CH
CCHCH3
|
|
CH3
CH2OH
O
||
CH2CCHCH3
(c)
(d)
|
HO — C — CH3
|
CH3
Identify the major product P in the following reaction:
OLi
O
O
||
||
CCH2CH2CH
OLi
(i)CH CH I THF
3
2
¾ ¾¾¾¾¾
¾® P
OEt
(ii) H 3O+
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O
CH3CH2O
O
(a) CH3 — CH2
O
(b)
OEt
OEt
O
O
O
(c)
OCH3CH2
(d)
OEt
OEt
CH2 — CH3
19.
The enolate ion that reacts with 3-buten-2-one to form (Y) is :
O
O
(Y)
O
O
O
(a)
(b)
O
(c)
(d)
O
14
O
CH3
20.
base
D
I
O
(A), (A) + CH3 —
H
O
HO–(dil)
D
(B)
H
Product (B) in the above reaction is :
O
(a) CH
3
H
14
14
Br
CH3
C
14
CH3
14
O
(c)
21.
(b)
O
O
(d)
H
H
O
||
HO H — C — D ¾ ¾¾®; Product of this Cannizaro reaction is :
(50%)
(a) D —
(c) D —
CO -2
CO -2
+ CH 2 DOD
(b) H — CO -2 + D — CO -2
+ CH 2 DOH
(d) D — CO -2 + CHD 2 OH
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22.
An organic compound with the molecular formula C 9 H 10 O forms a 2,4-DNP derivative,
reduces Tollen’s reagent and undergoes Cannizaro reaction, on vigorous oxidation it gives
1,2-benzenedicarboxylic acid. Structure of organic compound is:
(a)
(b)
CHO
CHO
O
CH3
(c)
(d)
CHO
23.
CHO
O
O
||
||
CH 3 ¾ C ¾ CH 2 ¾ CH 2 ¾ CH 2 ¾ CH 2 ¾ C ¾ H
¾®
KOH
Number of intramolecular aldol condensation product is :
(a) 1
24.
(b) 2
(c) 3
(d) 4
O3
( A) ¾ ¾¾¾
¾® ( B ) + (C )
C 7 H14
Zn AcOH
Compound (A) exist in geometrical isomers and (B) gives Cannizaro reaction.
(A) will be :
25.
CH 3
|
(a) CH 3 — CH — C == CH — CH 3
|
CH 3
(b) (CH 3 ) 3 CCH 2 — CH == CH 2
(c) (CH 3 ) 3 C — CH == CH — CH 3
CH 3
|
(d) CH 3 — C — CH 2 — CH == CH 2
|
CH 3
Which of the following compounds will not undergo Cannizaro reaction, when treated with
50% aqueous alkali?
O
||
(b)
(c) Me 2 CHCHO
(d) Ph — CH 2 — CHO
(a) Ph — C — H
O
CHO
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26.
O
O
||
||
H18O ¾® D — C —
H — C — D ¾ ¾¾
18
O - + CH 2 D — OH
Above reaction is known as :
(a)
(b)
(c)
(d)
Cannizaro reaction, Disproportionation reaction
Tischenko reaction, Disproportionation reaction
Cross Cannizaro reaction, Redox reaction
Tischenko reaction, Redox reaction
CH2
CH3
HO (Conjugate- addition)
+
27.
CH ¾ ¾¾¾¾¾¾¾® ( A) ; Product (A) is :
O
C
O
CH3
(a)
(b)
O
O
(c)
(d)
O
O
CHO
OH
(1) Ac O, AcONa
2
¾ ¾¾¾¾¾
¾® ( A) ; Identify product and name of reaction.
28.
(2) H 2O
O
(a)
, Aldol condensation
O
(b)
, Perkin reaction
O
O
O
(c)
, Cannizaro reaction
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CH == CH — CO2H
(d)
29.
, Claisen-condensation
Choose the most reasonable reaction intermediate for the following reaction.
O
O
HO–
(cat.)
O
(a)
(b)
O
O
(c)
(d) None of these
O
30.
O
OH
||
|
HO Na 2CO 3
® ( B)
CH 3 — CH — CH 2 — C — H ¾ ¾¾® ( A) ; 3HCHO + A ¾ ¾¾¾
(Retro aldol)
40°C
(82%)
Product (B) of the above reaction is :
31.
CH 2 — OH
|
(a) HO — CH 2 — C — CH 2 OH
|
CH 2 — OH
CHO
|
(b) HO — CH 2 — C — CHO
|
CH 2 — OH
CH 2 OH
|
(c) HO — CH 2 — C — CH 2 OH
|
CHO
CHO
|
(d) HO — CH 2 — C — CH 2 — CH 2 — OH
|
CH 2 — OH
OH -
D
CH 3 CH == CHCHO ¾ ¾¾® ¾¾® A; Product A is :
Aldol
condensation
(a) CH 3 (CH == CH) 3 CHO
(c) CH 3 (CH 2 CH 2 ) 3 CH == CH — CHO
(b) CH 3 CH 2 CH 2 (CH == CH) 2 CHO
(d) none is correct
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O
HO
32.
B. (A) and (B) are isomer : Identify ( B ) .
H2O
(A)
O
O
(a)
(b)
O
O
(c)
(d)
OH
+
-
O
H
HO
3
¾¾
¾® ( A) ¾ ¾
¾
® ( B ) ¾ ¾¾® (C ) ; Product (C) is :
Zn
33.
D
D
(72%)
O
O
(a)
(b)
CHO
O
(c)
(d)
C — CH3
O
O
34.
H ¾HCl/heat
¾¾¾¾® A. Product ( A) is:
+
O
O
||
(a)
(b) Ph - C - CH 2 - CH 2 - Ph
(c) Ph - CH = CH -CH - Ph
|
(d) Ph – CH = C = CH – Ph
OH
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35.
Which of the following reactant on reaction with conc. NaOH followed by acidification gives
the following lactone as the product ?
O
O
O
CO2H
C—OCH3
(a)
(b)
CO2H
CHO
CHO
CO2H
(c)
(d)
CO2H
CHO
Br
NaOH
36.
Product; Product is:
OH
OH
(a)
(b)
O
OH
OH
(c)
(d)
O
OH
O
37.
KOH
(P) ¾ ¾¾
®
D
s
(Q) ¾ ¾¾® Ph—CH2—OH + Ph—CO2
KOH
D
O3
(R) ¾ ¾
¾® P + Q, Structure of (R) is :
(a) Ph — CH == CH — CH 3
CH3
(c) Ph—C== CH—CH3
(b) Ph—CH== C
CH3
CH3
CH3
(d) CH3—C== CH2
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38.
The following reaction gives:
CHO
+ HCHO
conc.NaOH
?
OMe
OMe
CH2OH
CH2OH
+ CH3OH
(a)
+ HCO2
(b)
OMe
OMe
OMe
OMe
COOH
COOH
+ HCOOH
(c)
+ CH3OH
(d)
OMe
OMe
OMe
OMe
39.
Which of the following is not the product of an intramolecular aldol condensation ?
O
O
O
O
(a)
40.
(b)
(c)
(d)
Os
|
x = no. of compound better hydride donor than Ph — C — O s
|
H
s
O
s
O
(a)
Os
Os
(b)
CH3O
O2N
s
O
Os
(c)
CH3
Os
(d)
CH3
s
CH3 O
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41.
Choose the reactant whose aldol reaction would give jasmone.
O
s
HO
heat
(aldol reaction)
?
jasmone
O
O
(a)
O
(b)
O
O
(c)
(d)
O
42.
O
Compound X undergoes the following reaction sequence. What is the structure of compound
X?
OH
NaOH
Heat
H
Pd
1. LiAlH
2
4
¾® ¾ ¾¾® ¾ ¾¾
¾® ¾ ¾¾¾
®
X ¾ ¾¾
2. H 2O
(a)
(c)
43.
HO
(b) HO
O
(d) O
Predict the major product of the following reaction sequence
O
O
OLi
H
CH3
+ NaOH
H3C
1.
–H2O
Heat
2. H2O
CH3
O
(a)
O
O
O
(b)
CH3
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CH3
O
O
O
(c)
O
(d)
CH3
KOH
Hr
CHO ¾Conc.
¾¾¾
¾® ( A) ¾ ¾
¾®
D
D
CHO
44.
( B)
Cyclic product
Structure of ( B ) is :
O
O
(a)
45.
(d)
COOK
CH2OH
Which of the following is not the product of an intramolecular aldol condensation ?
O
O
O
(a)
46.
O
COOH (c)
CH2OH
(b)
O
(X)
(b)
Conc. KOH
(Y)
(c)
HÅ
O
(d)
O
D
O
Compound (X) is obtained by which of the following reaction ?
O
(a)
CH2—OH
CH2—OH
C—O—Et
2 moles of PCC
in CH2Cl2
2 moles of DIBAL-H
(b)
C—CH3
O
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O
O
C—Cl
2H2
(c)
CH2—C—Cl
H
47.
CH3MgBr
(d)
Pd – BaSO4
H
O == C—C == O
OH
O == C—C—OH
H
O H
Given reaction is Cannizaro reaction at normal concentration of base. Predict the order of
above reaction
(a) 1
48.
(A)
(b) 2
(c) 3
(1) O3/Zn
(2) conc. KOH
(d) 4
s Å
OH + HCO2K
HBr
(B)
CCl4
major
Product (B) is :
(a)
(b)
(c)
(d)
Br
Br
ANSWERS — LEVEL 1
1.
(a)
2.
(b)
3.
(a)
4.
(b)
5.
(b)
6.
(c)
7.
(b)
8.
(b)
9.
(b)
10.
(c)
11.
(a)
12.
(a)
13.
(a)
14.
(b)
15.
(a)
16.
(b)
17.
(b)
18.
(a)
19.
(c)
20.
(a)
21.
(c)
22.
(b)
23.
(c)
24.
(c)
25.
(d)
26.
(a)
27.
(c)
28.
(b)
29.
(c)
30.
(c)
31.
(a)
32.
(a)
33.
(c)
34.
(a)
35.
(c)
36.
(b)
37.
(b)
38.
(b)
39.
(c)
40. (b,c)
41.
(d)
42.
(d)
43.
(c)
44.
(a)
45.
(c)
46.
(a)
47.
(b)
48.
(b)
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Level - 2
1. Comprehension
Mechanism of Cannizzaros reaction of benzaldehyde is
O-
O
O
–
Ph
A.
HO
C
|
H
Ph
C
H + C
O
H
O
slow
C
OH + Ph
Ph
CO2 + Ph
Ph ¾¾® Ph
H
CH2
O–
CH2
OH
-
Which of the following reactants can undergo Cannizaro's reaction.?
O
(a) H
C
H
(b) R 3CCHO
(c)
(d) All of these
O
B.
C.
CHO
Order of the above reaction is:
(a) 1
(c) 3
Which of the following is best hydride donor in Cannizaro's reaction?
CHO
CHO
(a)
(b)
OMe
NO2
CHO
CHO
(c)
D.
E.
(b) 2
(d) 4
CH3
Cannizaro's reaction is:
(a) Reduction
(c) Oxidation
(d)
Cl
(b) Disproportionation reaction
(d) Ion - exchange reaction
Which of the following cannot undergo intramolecular Cannizaro's reaction?
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(a) H
(c) Ph
2.
O
O
C
C
H
O
O
C
C
(b) H
Ph
(d) H
O
O
C
C
O
O
C
C
Ph
H
Aldol condensation proceeds by carbon-carbon bond formation between an enolate donor
and a carbonyl acceptor. For each of the following aldol products (a through e) select a
donor and an acceptor compound from the list at the bottom of the page (compounds A
through H). Write the letter corresponding to your selection in the appropriate answer box.
Aldol Product
Donor
Acceptor
OH
a.
CHO
O
b.
OH
O
c.
CH
d.
(CH 3 ) 2 C(OH)CH 2COCH 3
CO2C2H5
e.
CO2C2H5
CHO
(A)
(B)
CHO (D)H C == O
2
(C)
O
O
(E)
O
(F) H2C
CO2C2H5
CO2C2H5
(G)
H3C
CH3
(H)
CHO
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3. Comprehension
During an experimental workup procedure, a chemist treated a starting material with NaOH
in the solvent acetone [(CH 3 ) 2 C == O]; however, the starting material was recovered
unreacted. Instead, the chemist isolated a small amount of Product A (shown below).
Product A
The chemist determined that Product A resulted from the aldol self-condensation of acetone.
Product A was identified based on the following observations.
Observations about Product A
1. Elemental analysis of Product A indicated that it consisted only of carbon, hydrogen, and
oxygen.
2. product A had a molecular weight of 116 g/mol.
3. Product A was a methyl ketone because it gave a positive iodoform test.
4. When product A was treated with Br 2 in CCl 4 , the red bromine colour persisted, because
no carbon-carbon double bonds were present to react with the bromine.
The structure of Product A was further confirmed when treatment with hot sulfuric acid
resulted in the corresponding dehydration product, Product B.
A.
What is the molecular weight of a compound that undergoes an aldol self-condensation
reaction to result in a b-hydroxy ketone with a molecular weight of 144 ?
(a) 70 g/mol
(b) 72 g/mol
(c) 74 g/mol
(d) 76 g/mol
B.
The aldol self-condensation of acetone is an equilibrium that favours acetone over its
condensation product. Which of the following experimental modifications is most likely to
shift the position of equilibrium toward Product A ?
(a) Using only a catalytic amount of NaOH
(b) Using only a catalytic amount of acetone
(c) Removing Product A as it is formed
(d) Increasing the reaction temperature to the boiling point of acetone
C.
Based only on observation 1 and 2, which of the following compounds could have been
Product A ?
O
OH
|
||
(a) CH 3CH CH 2CH 2CH 2CH 2CH 3
(b) CH 3C CH 2 CH CH 2CH 2CH 3
|
CH 3
OH
(c) CH 2 == CHCH 2 - O - CH 2CH 2CH 3
(d)
OH
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D.
When a drop of Br 2 in CCl 4 is added to Product B, the resulting solution will be :
(a) colourless, because Product B does not contain a carbon-carbon double bond
(b) colourless, because Product B contains a carbon-carbon double bond
(c) red, because Product B does not contain a carbon-carbon double bond
(d) red, because Product B contains a carbon-carbon double bond
E.
Which of the following compounds from the passage will give a positive iodoform test ?
(a) Product A only
(b) Product A and Product B
(c) Product A and acetone only
(d) Product A, Product B, and acetone
4. Comprehension
A
O3
B+C
conc. KOH
Benzyl alcohol + salt of benzoic acid
O
dil. KOH
CH3—CH—CH2—C—H
HCN
OH
D
A.
B.
C.
H3O
D
r
E
Structure of A is :
(a) H 2C == CH — CHO
(c) Ph — C == CH 2
|
CH 3
(b) Ph — CH == CH — CH 3
(d) Ph — CH == C — CH 3
|
CH 3
Structure of (B) and (C) differentiated by :
(a) Tollen’s reagent
(c) 2,4-DNP
(b) Fehling solution
(d) NaHSO 3
Structure of E is :
OH
(b)
O
HO
O
(a)
Me
OH
OH
(d)
O
O
(c)
O
O
O
5. Comprehension
An organic compound ‘P’ with molecular formula C 8 H 8 O forms an organic red ppt with 2,
4-DNP gives yellow ppt. on heating with I 2 in presence of NaOH. It neither reduces Tollen’s
or Fehling reagent nor does it decolourise Br 2 water or Baeyer’s reagent. On drastic
oxidation with chromic acid (H 2 CrO 4 ) it gives an acid (Q) having molecular formula
C 7 H 6 O 2.
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A.
Identify compound P :
O
C—H
(a)
(b)
H3C
CH3
B.
O
OH
O
C—CH3
(c)
CH3
(d)
(c)
(d)
(c) 4
(d) 6
H2C
NaOH/CaO / D
Q ¾¾¾¾¾¾® R (Major product)
R will be :
Ph
(a)
C.
(b)
s
dil. OH
CH 3 MgBr (1mole)
P ¾¾¾® S ¾¾¾¾¾¾®
Å
D
H 3O
No. of stereoisomer in the final product T :
(a) 2
(b) 3
Subjective Problems
O
O
1.
O
OH
H
H
OH
(A)
OH
H
H
(C)
(B)
O
OH
O
O
O
HO
O
O
HO
(F)
(G)
(H)
H
OH
(E)
(D)
OH
O
OH
HO
(I)
(J)
X = Number of compound obtained by aldol reaction
Y = Number of compounds react with NaHCO 3
Sum of X + Y is
2.
In the scheme given below, the total number of intramolecular aldol condensation products
formed from ‘ Y ’ is :
1. NaOH ( aq)
1. O
3
¾ 2¾¾¾
¾® Y ¾ ¾¾¾¾
®
2. heat
. Zn , H O
2
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3.
O
HO
||
KOH
¾®
CH 3 — C — CH 3 + x HCHO ¾ ¾
HO
HO
O
OH
C
OH
HO
x = moles of HCHO consumed.
4.
Value of ( x) will be
O
O
||
||
KOH( aq.)
® ( X)
CH 3 — C — CH 3 + CH 3 — CH 2 — C — CH 3 ¾ ¾¾¾¾
D
X = number of aldol condensation product (including stereoisomer).
Find out the value of ( X ) .
ANSWERS — LEVEL 2
1.
A – d; B – c; C – a; D – b; E - c
2.
a – Donor = C, Acceptor = C; b – Donor = E, Acceptor = D;
c – Donor = B, Acceptor = A; d – Donor = G, Acceptor = G; e – Donor = F, Acceptor = B
3.
A – b; B – c; C – d; D – b; E - d
4.
A – b, B – b, C – c
5.
A – c, B – a, C – c
Subjective Problems
1. 6
2. 3
3. 6
4. 9
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9
CARBOXYLIC ACID AND THEIR DERIVATIVES
Level - 1
1. Identify C in the following sequence of reactions :
CO2H
SOCl
NH
PO
heat
2
3
4 10
¾ ¾¾
¾
® A ¾ ¾¾
® B ¾ ¾¾
® C(C 8 H 13 N)
CH3
OH
CN
CN
(a)
(b)
(c)
CH3
CN
(d)
CH3
CH3
CH3
2. Saponification (basic hydrolysis) of C 6 H 5 C O CH 3 will yield :
||
[ O = mass – 18 isotope of oxygen]
O
||
(a) C 6 H 5 — C — O - +HO CH 3
(c) C 6 H 5 C O - + H O -
O
O
||
(b) C 6 H 5 — C — O - +H OCH 3
(d) C 6 H 5 CO - + HOCH 3
||
O
||
O
O
C – Cl
3.
Me NH
2
¾ ¾¾
¾®
0°C, 2h
(X)
86-89% (yield);
(3 equivalent)
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Product (X) of the reaction is :
OH
O
Me
N
(a)
C – NMe2
Me
(b)
NMe2
O
C–H
(c)
(d)
4. Which of the following is the correct order of decarboxylation of b-keto carboxylate anion ?
O
O
O
O
O
O
O
O
–
O
–
– R
–
R–C
R
R
O
O
O
F
Cl
NO2
CN
(a)
(a) a > b > c > d
O
(c)
(b)
(b) c > d > a > b
(d)
(c) c > d > b > a
(d) d > c > a > b
O
ClC
CCl
5.
+ CH 3 - NH 2 ¾¾® Product of the reaction is :
(A)
CH3
|
N
(a) O
N
O
(b) HO
CH3
O
O
NH
|
NH
(c)
(d)
O
6. Which b-keto acid shown will not undergo decarboxylation ?
CO2H
O
(a)
||
O
O
(b)
CO2H
O
||
(c) Ph - C - CH 2 - CO 2 H
O
||
(d) CH 3 - C - CH 2 - CO 2 H
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7. Choose the response that matches the correct functional group classification with the
following group of structural formulas.
H
N
O
(a)
(b)
(c)
(d)
H
N
O
Anhydride
Lactam
Imide
Imide
O
O
Lactam
Imide
Lactone
Lactam
O
Lactone
Lactone
Anhydride
Lactone
OH
CO2H
8.
(1) Et - Li(3- eq.)
(P)
¾ ¾¾¾¾¾¾®
(2) H + , H 2O
OH
; Product (P) of the reaction is :
(65% yield)
OH
(a)
Et
(b)
O
OEt
OH
Et
OEt
Et
Et
O
(c)
Et
OH
Et (d)
Et
OH
9.
OH
(X) + H 2 O
conc. H2SO4
89-91% yield
OH
(Lactic acid)
Product (X) of the reaction is :
O
O
OH
(a)
(b)
O
O
OH
O
O
(c)
(d)
O
OH
OH
MeO
OMe
CO2Et
10. EtO2C
H OÅ
3
¾ ¾¾
¾® (A) , Product (A) obtained is :
D
O
O
CO2H
CO2Et
O
(a)
O
O
(b)
(c)
(d)
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11. Which of the following acid on heating gives geometrical isomers as a product ?
CO2H
OH
|
CO2H
(a) CH 3 - CH - CO 2 H
(b)
Cl
(c) CH 3 - CH - CH 2 - CO 2 H
(d) All of these
|
OH
O
MeNH
PCl
MeOH
2
3
¾® A ¾ ¾¾
® B ¾ ¾¾¾
® C ; Product (C) of the reaction is :
O ¾ ¾¾
12.
||
O
O
O
||
C – NH – Me
C – Cl
(a)
(b)
C – NH – Me
C – O – Me
||
O
O
||
C – Cl
O
O
NH2
(c)
(d)
C – NH2
||
O
OMe
O
O
NH - NH
LiAlH
PCC
2
2
4
¾
® A ¾ ¾¾® B ¾ ¾¾¾
¾
® C , Product (C) is :
O ¾ ¾¾
13.
||
O
O
NH
(a)
OH
|
N
(b)
N
NH
(c)
|
OH
O
Cl
|
NH2
N
N
(d)
NH2
O
- CO
aq KOH
HCl
2
– ¾ ¾¾
® A ¾¾
¾® B ¾ ¾¾¾® C. Product (C) is :
O
14.
Cl
O
||
(a) CH 3 — CH 2 — C — H
O
(b)
(c)
(d)
H
OH
|
OH
O
CH3
CH3
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Cl
K CO
2
3
+R - CH 2 - NH 2 ¾ ¾¾
¾
® ( A)
O
15.
THF
(71%)
O
In above reaction identify major product (A) of the reaction:
(a)
OH
(b)
N – CH2 – R
N – CH2 – R
O
O
NH – R
(c)
OH
(d)
O
N–R
O
O
16. An optically active compound ‘X’ has molecular formula C 4 H 8 O 3 . It evolves CO 2 with
NaHCO 3 . ‘X’ reacts with LiAlH 4 to give an achiral compound. ‘X’ is :
(a) CH 3 CH 2 CHCOOH
|
OH
(b) CH 3 CHCOOH
|
Me
(c) CH 3 CHCOOH
|
CH 2OH
O
(d) CH 3 CHCH 2 COOH
|
OH
||
17. CH 3 - C - O - CH 2 - CH 3 + H – O – ¾¾® (O = O 18 ) One of the product of the reaction is :
O
||
(a) CH 3 - C - O - H
O
(b) CH 3 - CH 2 - O -H
(c) CH 3 - C - O –
(d) CH 3 - CH 2 - O –
||
O
COCH2CH3
18.
CH3CH2OC
O
KOH
H O+
PCl
LiAlH
H+ / D
3
5
4
¾® ¾ ¾¾
® ¾ ¾¾
¾
® ¾ ¾¾
¾® ( X )
COCH2CH3 ¾ ¾¾® ¾ ¾¾
O
Product (X) is :
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(a)
(b)
(c)
(d)
19. Identify final product in the following reaction;
D
CH 3 CHCOOH ¾¾® Product
|
OH
O
O
O
CH3
(a)
||
(b) CH 2 == CHCO 2 H (c) CH 3 — C CO 2 H
H3C
(d) CH 3 CH 2 OH
O
O
20. Select the final product from this sequence of reactions.
NaOEt
CH I
NaOEt
CH CH CH Br
3
3
2
2
Acetoacetic ester ¾ ¾¾
¾® ¾ ¾¾
® ¾ ¾¾
¾® ¾ ¾¾¾¾¾
®
O CH 3
||
CH 3
|
|
(a) H 3 C - C -C - COOC 2 H 5
(b) H 3 C -C - CH 2 COOC 2 H 5
|
|
CH 2CH 2CH 3
CH 2CH 2CH 3
CH 3
H
|
|
(c) H 3 C - C - CH 2 COOC 2 H 5
(d) CH 3 CO – C – CH 2 COOC 2 H 5
|
|
CH 3
CH 2CH 2CH 3
Et
CO2CH2 – CH3
H O, H SO
O
21.
2
2
4
¾ ¾¾¾¾
¾
® (A) ; Product (A) will be :
heat
CO2Et
O
O
O
O
CO2H
(a)
(b)
(c)
(d)
(i) Na
22. CH 2 (CO 2 Me) 2 + ? ¾ ¾¾¾
¾® CH(CO 2 Me) 3
(ii) AcOH
Which of the following reactants will complete the above reaction ?
(a) CH 2 (CO 2 Me) 2
(b) (CO 2 Me) 2
(c) Cl - CO 2 Me
(d) COCl 2
23. Arrange the following in order of increasing reactivity (least ¾® most) towards nucleophile
O
O
||
||
CH 3C OCHCH 3
1
(a) 1 < 2 < 3
(c) 1 < 3 < 2
CH 3C Cl
2
O
||
CH 3 C NHCH 3
3
(b) 3 < 1 < 2
(d) 2 < 1 < 3
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24. Choose the best sequence of reactions for transformation given. Semicolons indicate
separate reaction steps to be used in the order shown.
O
||
?
C NH CH3
CO2CH3 ¾¾® H3C
H3C
(a) H 3 O + ; SOCl 2 ; CH 3 NH 2
(b) HO - H 2 O ; PBr 3 ; Mg; CO 2 ; H 3 O - ; SOCl 2 ; CH 3 NH 2
(c) LiAlH 4 ; H 2 O; HBr; Mg; CO 2 ; H 3 O + ; SOCl 2 ; CH 3 NH 2
(d) None of these would yield the desired product
25. A key step in the hydrolysis of acetamide in aqueous acid proceeds by nucleophilic addition
of :
+
O
OH
||
||
(a) H 3 O + to CH 3 C NH 2
+
+
(b) H 2 O to CH 3 C NH 2
+
OH
||
OH
||
-
(d) HO to CH 3 C NH 2
(c) H 3 O to CH 3 C NH 2
26. Which reaction is not possible for acetic anhydride ?
O
O
||
||
||
||
+
(a) (CH 3 C ) 2 O + 2HN(CH 3 ) 2 ¾® CH 3 C N(CH 3 ) 2 + CH 3 CO -2 + H 2 N(C H 3 ) 2
O
O
(b) (CH 3 C ) 2 O + CH 3 CH 2 OH ¾® CH 3 C OCH 2 CH 3 + CH 3 CO 2 H
O
O
||
||
AlCl
3
(c) (CH 3C ) 2 O + C 6 H 6 ¾ ¾¾
® CH 3 C C 6 H 5 + CH 3 CO 2 H
O
O
||
||
(d) (CH 3 C ) 2 O + NaCl ¾® CH 3 C Cl + CH 3 CO -2 Na +
27. All but one of the following compounds react with aniline to give acetanilide. Which one
does not?
O
NH2
Aniline
NHCCH3
Acetanilide
O
||
(a) CH 3 C —Cl
O
||
CH3
(b) H3C
O
(d)
O
||
OCCH3
O
||
(c) CH 3 C —H
O
||
28. Which of the following best describes the nucleophilic addition step in the acid-catalyzed
hydrolysis of acetonitrile (CH 3 CN) ?
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H3C – C º N
–
O
(a)
+
H3C – C º N – H
–
O
(b)
H
H
+
(c) H3C – C º N
(d) H3C – C º N – H
O
O
H
H
H
H
29. The major product expected, when Phthalamide is treated with NaOH, is :
OH
OH
(a)
(b)
OH
ONa
O
O
O
||
ONa
ONa
(c)
O
(d)
||
O
O
O
30. Which of following acid remains unaffected on heating ?
(a) malonic acid
(b) maleic acid
(c) Fumaric acid
(d) Succinic acid
31. Br
(
)
n
NaOEt
¾® cyclic product
Br + CH 2 (CO 2 Et) 2 ¾ ¾¾
EtOH
At which value of n the formation of six membered ring takes place ?
(a) n = 2
(b) n = 3
(c) n = 5
(d) n = 6
O
32.
LiAlH (excess)
4
¾ ¾¾¾¾¾
® Product of the reaction is :
N
H 2O
O
(a)
NH2
CH2OH
(b)
CH2OH
OH
(c)
33.
CO2H
CO2H
N
(d)
N
OH
D
D
¾ ¾¾¾® ¾ ¾¾¾® , Product of the reaction is :
( -CO 2 )
( - H 2O )
CO2H
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(a) cis-anhydride
(c) both (a) & (b)
(b) trans--anhydride
(d) mono-basic acid
CO2H
34.
(i) EtOH, HCl
¾ ¾¾¾¾® ( A)
(ii) EtMgBr
||
(iii) H + D
O
Product (A) of the reaction is :
CH3
CO2Et
CO2Et
(a)
(b)
O
HO Et
O
O
C – CH3
C – CH3
(c)
(d)
CH3
O
35.
OH
CH 2 – O – COR
|
CH – O – COR 2 + 3NaOH ¾® (A) + Salt of fatty acid (soap)
|
CH 2 – O – COR 3
Product (A) of the reaction is :
(a) Ethylene glycol
(c) Glyceryltrinitrate (explosive)
(b) Glycerol
(d) Cumene hydrogen peroxide
–
HO
36. CH 3 - CH - OAc ¾ ¾¾
® Product of the reaction is :
|
Et
( d)
(d=dextro rotatory)
Et
|
(a) CH 3 -CH - OH
(b) CH 3 - CH - OH
|
(d)
Et
(l)
(c) CH 3 - CH - OH
|
(d) CH 3 - C = CH 2
Et
|
CH 3
(d) & (l)
O
||
37. Ph - CH = CH -C - O - H
(i) SOCl2
(ii) NH2
(A) ; Product (A) of the reaction is :
O
O
||
||
(a) Ph - CH = CH -C - CH 2 - NH
O
(b) Ph - CH = CH -C - NH
(c) Ph - CH = CH - C – H
(d) Ph – CH = CH – NH
||
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O
O
||
38. Ph - C - Cl +
¾¾® ( A) ; Identify the product (A).
N
|
H
(Morpholine)
(Major)
O
O
(a) Ph – C – O
(b) Ph – C – N
N–H
O
O
O
O
||
(c) Ph – C – N
(d) Ph - C - NH 2
OH
OMe
39.
O
Conc. HCl
+ MeOH
+
O
O
Above reaction is an example of :
(a) Esterification
(b) Saponification
(c) Hydrolysis
(d) Trans Esterification
40. Which of the following is an intermediate formed in the reaction shown below ?
O
||
CH 3 - C - Cl + NH 3 ¾¾® Intermediate ¾¾® product.
O
||
Å
(a) CH 3 - N H 3
OH
(b) CH 3 - C Å
O–
(c) Cl - C - Cl
(d) CH 3 - C - Cl
|
|
|
|
Å NH 3
Å NH 3
O
R
O
41. R
O
O
O
R
NaOH, H O
2
¾ ¾¾¾¾
® Product
100°C
(several hours)
O
(Principal component of coconut oil.)
Product is obtained in the above reaction is :
OH
(a) R - CO 2 Na
(b)
(c) Both (a) and (b) (d) None of these
OH
OH
42. The reaction of sodium acetate with acetyl chloride proceeds through which of the following
mechanisms ?
O
O
O
O
–
|| –
(a) CH3 – C – O + CH3 – C – Cl
(b) CH3 – C – O
+ CH3 – C – Cl
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O
O
–
(c) CH3 – C – O
+
O
CH3 – C – Cl
O
–
(d) CH3 – C – O
+
Cl – C – CH
3
43. Which is the major product of the following reaction ?
O
||
H S
2
CH 3 - C - Cl ¾ ¾¾
® product
O
OH
|
S
||
(a) CH 3 -C - Cl
(b) CH 3 - C - SH
|
O
||
||
(c) CH 3 - C - Cl
O
||
(d) CH 3 - C - S - C - CH 3
SH
44. Which is the major product of the following reaction ?
O
D
O + CH 3 - NH 2 ¾®
product
O
O
N – CH 3
N – CH3
(a)
O
(b)
O
O
O
O
||
||
(c) HO - C - CH 2 - CH 2 - C - NH - CH 3
O
O
||
||
(d) CH 3 - NH - C - CH 2 - CH 2 - C - NH - CH 3
45. Ethanoic acid + 3-methyl-1-butanol
O
(a)
traces
H2SO4
( A); Compound (A) is :
(b)
O
O
O
||
O
O
(c)
(d)
O
O
O
||
C
O
46.
PCl
LiAlH
PCC
HO –
5
4
¾ ¾¾
®( A) ¾ ¾¾
¾
®( B ) ¾ ¾¾®(C ) ¾ ¾¾®( D)
D
C
O
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–
CO2
CH2 – OH
(a)
(b)
–
CO2
–
CO2
–
CH2 – O
CH2 – OH
(c)
(d)
CH2 – OH
–
CH2 – O
47. Which of the following compounds will undergo decarboxylation on heating ?
CO2H
CO2H
O
O
O
CO2CH3
CO2H
O
1
4
3
2
(a) 2 and 3
(b) 3 and 4
(c) 3 only
(d) 1 and 4
48. Which one of the following is not an intermediate in the generally accepted mechanism for
the reaction shown below ?
O
O
||
H SO
||
2
4
CF3 C OH + CH 3 CH CH 3 ¾ ¾¾
¾
® CF3 C O CH CH 3 + H 2 O
|
|
OH
CH 3
–
+
49.
OH
||
(a) CF3C – OH
O
|
(b) CF3C – OCH(CH)
3 2
|
OH
OH
|
(c) CF3C – OCH(CH3)2
|
+
OH2
OH
|
(d) CF3C – OCH(CH3)2
|
OH
3 eq. EtOH
RO
(a) RO
CO2H
¾ ¾¾¾¾¾
¾® (A); Product A is :
dry HCl gas
(major product);
(b) RO
CO2R
CO2Et
O
||
(c) EtO
CO2Et
(d) R - O - C - O - Et
50. Identify the compound C in the following sequence :
HCl, H O
1. LiAlH
2
4
(CH 3 ) 2 CHCH 2 C º N ¾ ¾¾¾
¾® compound A ¾ ¾ ¾¾
¾
® compound B
2. H 2O
PCC
CH 2Cl 2
¾ ¾¾
¾® compound C
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O
O
||
||
(a) (CH 3 ) 2 CHC CH 3
(b) (CH 3 ) 2 CHCH 2 C OH
O
O
||
||
(c) (CH 3 ) 2 CHCH 2 C H
(d) (CH 3 ) 2 CHC CH 2 OH
51. What is the final product (B) of this sequence ?
CH3
Br2
1. KCN
light
2. H 3O , heat
¾ ¾¾® A ¾ ¾¾¾¾
¾® B
+
CH3
CH3
CO2H
CH2CO2H
CO2H
(a)
(b)
(c)
(d)
CO2H
52. Which of the following undergoes decarboxylation most readily on being heated ?
O
(a)
(b)
OH
O
HO
O
(c) HO
O
O
O
(d)
OH
O
HO
53. What is compound Z ?
NaCN
H O
+
O
CH CH OH
3
2
3
CH 3 CH 2 CH 2 Br ¾ ¾¾
¾® X ¾ ¾¾
® Y ¾ ¾¾¾¾
®Z
+
heat
H
O
||
(a) CH 3 CH = CHC OH
(b) CH 3 CH 2 CH 2 CH = NOCH 2 CH 3
O
(c) CH 3 CH 2 CH 2 CH(OCH 2 CH 3 ) 2
(d) CH 3 CH 2 CH 2 C OCH 2 CH 3
||
CN
CN H 3O Å /D
CN ¾¾® (A); Product (A) of the reaction is :
CN
O
O
54.
O
(a)
O
(b)
O
O
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O
CO2H
(c)
(d)
O
CO2H
O
55. CH 3 - CH = CH - CH 2 - CO 2 H ¾¾® (X) (major); Product (X) is :
D
(a) CH 3 - CH = CH - CH 3
(b) CH 3 - C = CH 2
(c) CH 3 - CH 2 - CH = CH 2
CH 3
(d) CH 3 - CH = CH 2
O
|
O
||
||
56. H - O - C - (CH 2 ) n - C - O - H ¾¾® product , At what value of (n) given compound will
D
not evolve CO 2 gas ?
(a) n = 5
(b) n = 4
(c) n = 2
(d) n = 1
CO 2 H
|
57. (CH 2 ) n ; If (n = 4) then di-carboxylic acid would be known as :
|
CO 2 H
(a) Malonic acid
(b) Succinic acid
(c) Adipic acid
(d) Oxalic acid
2H O
2
¾ ¾¾
® ( A)
58.
O
O
O
C
O
Product (A) of the above reaction is :
HO
(a)
CH3
OH
(b) O
CO2H
CO2H
CO2H
OH
CO2H
O
(c) HO
HO
CO2H
CO2H
(d)
C—H
HO
H
HO
O
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2H 2
Pt
59. (A)
KM
Wa
nO
rm
con 4
c.
O
CO2H
CO2H
O
+ HO — C — C — O — H
cis-cyclo hexane
1,2-dicarboxylic acid
Identify (A).
(a)
(b)
CO2H
(c)
(d)
CO2H
60. CH3
CH3
How many product will be formed when above compound undergo de-carboxylation?
(a) 0
(b) 1
(c) 2
(d) 3
CH3
61.
H
H
H
H
D
¾ ¾¾
¾® Product of the reaction is :
( -CO 2 )
CO2H
H
CH3
H
CO2H
(a)
CH3
H
H
H
H
CH3
(b)
H
H
H
CH3
H
H
H
H
CO2H
H
CO2H
CH3
H
H
(c) Both (a) and (b)
(d) none of these
62. Products obtained in the given reactions are shown below.
CO2H
CO2H
Br
(cis)
Br
CO2H
D
CO2 + x ,
CO2H Br
Br
D
CO2 + y
(trans)
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The number of possible products for x and y are :
(a) 1, 1
(b) 1, 2
(c) 2, 1
O
–Å
(1)
CH2 – Br
N K + DMF
O
63.
( A)
(2) HO– /H2O
(Benzyl bromide)
(d) 2, 2
( 81%)
Product ( A) of the above reaction is :
(a) Ph - NH 2
(b) Ph - CH 2 - NH 2
(c) Ph - CH 2 - NH - CO 2 H
(d) Ph - CH 2 - NH - CHO
64. Which of the following pair is C 2 -epimer ?
(a) D-Glucose, D-Maltose
(b) D-Glucose, D-Mannose
(c) D-Allose, D-Ribose
(d) D-Glucose, D-Arabinose
65. Total number of enol possible for the compound formed during given reaction will be
(including stereoisomer):
O
||
CH 3 MgBr + CH 3 CH 2 — C — Cl ¾®
(a) 2
66.
(b) 3
(c) 4
(d) 5
What is the product of the following reaction ?
O
O
O
H O+, H O
3
2
¾ ¾¾¾
¾®
O
O
O
OH
(a) HO
(b)
HO
O
O
OH
O
O
O
O
(c)
(d)
HO
O
67.
OH
O
O
HO
OH
CH3
(i) KBrO, D
D
¾ ¾¾¾
¾® ( X ) ¾¾® (Y )
( i) H+
COOH
Hence the product (Y ) in the above sequence of reactions, is :
O
O
O
OH
COOH
(a)
(c)
CH3 (b)
(d)
CH3
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O
O
C—NH2
C—NH2
15
s
OH / Br
¾ ¾¾¾2¾® Products are :
and
68.
(Intramolecular
migration)
CH3
C2H5
15
and
(a)
CH3
Et
15
NH2
NH2
NH2
and
(c)
70.
CH3
15
NH2
NH2
and
(b)
Et
CH3
69.
15
NH2
NH2
NH2
and
(d)
CH3
Et
Et
base
CH 3 CH 2 CH(OH)CH(CH 3 ) 2 + CH 3 COCl ¾¾®
CH 3 CH 2 CH(OCOCH 3 )CH(CH 3 ) 2 + HCl
In the above reaction, if the reactant alcohol is a pure R-isomer the product would.
(a) have configuration inverted at the chiral atom
(b) be a racemic mixture
(c) have the same configuration at the chiral atom
(d) be optically inactive
The order of S N 1 reactivity in aqueous acetic acid solution for the compounds
O
H3C—C—CH2—Cl
H3C—CH2—CH2—Cl
(H3C)3C—Cl
(1)
(2)
(3)
(a) 1 > 2 > 3
(b) 1 > 3 > 2
(c) 3 > 2 > 1
(d) 3 > 1 > 2
ANSWERS — LEVEL 1
1.
(b)
2.
(b)
3.
(a)
4.
(c)
5.
(a)
6.
(b)
7.
(d)
8.
(b)
9.
(b)
10.
(b)
11.
(d)
12.
(b)
13.
(b)
14.
(a)
15.
(b)
16.
(c)
17.
(a)
(c)
18.
(b)
19.
(a)
20.
(a)
21.
(b)
22.
(c)
23.
(b)
24.
25.
(b)
26.
(d)
27.
(c)
28.
(d)
29.
(c)
30.
(c)
31.
(b)
32.
(c)
33.
(a)
34.
(a)
35.
(b)
36.
(a)
37.
(b)
38.
(b)
39.
(d)
40.
(d)
41.
(c)
42.
(c)
43.
(b)
44.
(c)
45.
(b)
46.
(a)
47.
(c)
48.
(b)
49.
(b)
50.
(c)
51.
(d)
52.
(d)
53.
(d)
54.
(d)
55.
(c)
56.
(c)
57.
(c)
58.
(c)
59.
(b)
60.
(b)
61.
(c)
62.
(c)
63.
(b)
64.
(b)
(b)
66.
(c)
67.
(c)
68.
(b)
69.
(c)
70.
(c)
65.
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Level - 2
1. Match the Column (I) and (II). (Matrix)
Column (I)
Column (II)
Reaction
Products formed
CH3
(a)
HO2C
H
CO2H
¾¾®
D
D
(p)
Diastereomers
CO2H ¾¾®
(q)
Racemic mixture
(r)
Meso compound
(s)
CO 2 gas will evolve
Ph
CH3
(b)
HO2C
D
Et
CO2H
CO2H
¾¾®
(c)
D
CH3
(d)
CO2H
CO2H
¾¾®
D
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Subjective Problems
O
1.
CO2H
HO2C
HO2C
CO2H ¾¾® ( X ) mole of CO 2 ­ ;
D
HO2C
CO2H
O
(Y )
b- Keto acid
¾¾
®
D
Ph
(Y ) is including stereoisomers. Value of ( X + Y ) will be
ANSWERS — LEVEL 2
1. a – p, s; b – q, s; c – p, s; d – r
Subjective Problems
1. 8
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487
10
AMINES
Level - 1
1.
In which of the following reaction cyanide will be obtained as a major product ?
O
O
||
||
NaOH
(i) LiAlH 4
(b) Ph - C - NH 2 ¾ ¾¾
(a) Ph - C - CH 3 ¾ ¾¾¾
¾®
¾
®
+
Br2
(ii) H 3O
O
||
P4O10
(c) Ph - C - NH 2 ¾ ¾¾
®
O
||
SOCl
NH 3
(d) Ph - C - O - H ¾ ¾¾2 ® ¾ ¾¾
®
NH2
HNO
2
¾ ¾¾
¾
® A (Major) :
2.
Product ( A) is :
OH
(a)
NH–NO2
(b)
(c)
O–NO
(d)
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3.
4.
Which of the following alkene cannot be prepared by de-amination of n-Bu – NH 2 with
( n- Butyl)
NaNO 2 HCl ?
(a) 1-butene
(b) cis-2-butene
(c) trans-2-butene
(d) Iso-butene
Predict the major product P in the following reaction.
Me
OH
Me
Me
HNO
2
¾ ¾¾
¾
® P
NH2
Me
O
(a)
Me
OH
Me
(b)
Me
Me
Me
Me
OH
(c)
Me
OH
Me
(d)
Me
CH2
OH
Me
NaNO
2
¾ ¾¾¾
® (A); Product of this reaction is :
5.
H 2SO 4
NH2
(a)
(b)
(c)
(d)
OH
HNO
2
¾
® ( A) +
CH2 – NH2 ¾ ¾¾
6.
48%
A will be :
7.
+ CH2 = CH – CH2 – CH2 – OH
47%
CH2OH
(a) CH 2 = CH -CH - CH 3
|
OH
(b)
(c)
(d)
Which of the following isomers of C 8 H 9 NO is the weakest base ?
(a) o-Aminoacetophenone
(b) p-Aminoacetophenone
(c) m-Aminoacetophenone
(d) Acetanilide
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8.
Rank the following compounds in order of increasing basic strength. (weakest ® strongest) :
O
||
NH2
NH2
CH2NH2
CNH2
NO2
9.
10.
CH 3
|
(d) CH 3 CCH 2 CHN(CH 3 ) 2
|
|
CH 3 OH
CH 3 N(CH 3 ) 2
|
|
(c) CH 3 CCH 2 CHN(CH 3 ) 2
|
CH 3
11.
4
3
2
1
(a) 4 < 2 < 1 < 3
(b) 4 < 3 < 1 < 2
(c) 4 < 1 < 3 < 2
(d) 2 < 1 < 3 < 4
Which of the following arylamines will not form a diazonium salt on reaction with sodium
nitrite in hydrochloric acid ?
(a) m-Ethylaniline
(b) p-Aminoacetophenone
(c) 4-Chloro-2-nitroaniline
(d) N-Ethyl-2-methylaniline
Identify product D in the following reaction sequence :
CH 3
1. LiAlH 4
|
(CH 3 )2 NH
K 2Cr2O7 ; H 2SO 4
SOCl
diethyl ether
¾® D
¾® A ¾ ¾¾2 ® B ¾ ¾¾¾
¾® C ¾ ¾¾¾¾
CH 3 – C – CH 2 CH 2 OH ¾ ¾¾¾¾¾
(2 mole)
2. H 2O
H 2O, heat
|
CH 3
CH 3
CH 3
|
|
(b) CH 3 CCH 2 CH 2 N(CH 3 ) 2
(a) CH 3 CCH 2 C º N
|
|
CH 3
CH 3
Which one of the following is best catalyst for the reaction shown below ?
KCN
benzene
CH 3 (CH 2 ) 8 CH 2 Br ¾ ¾¾® CH 3 (CH 2 ) 8 CH 2 CN
(a)
(c)
12.
CH3Cl
+
–
CH2N(CH3)3Cl
(b)
NH2
(d)
O
||
NHCCH3
The major products obtained from the following sequence of reactions are :
CH I
Ag O
heat
2
3
(CH 3 ) 2 CHCH 2 N(CH 2 CH 3 ) 2 ¾ ¾¾
® ¾ ¾¾
® ¾ ¾¾® products
H 2O
(a) (CH 3 ) 2 CHCH 2 NH 2 + H 2 C = CH 2
(b) (CH 3 ) 2 NCH 2 CH 3 + H 2 C = C(CH 3 ) 2
CH 3
|
+
(c) (CH 3 ) 2CHCH 2 N CH 2 CH 3 + H 2 C = CH 2 (d)(CH 3 ) 3 N CH 2 CH 3 I - + H 2 C = CH 2
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13.
Which amine yields N-nitroso amine after treatment with nitrous acid (NaNO 2 ,HCl) ?
(a)
CH2NH2
(b) H3C
(c)
N
(d)
NH2
NHCH3
H
OH HNO
2
¾
® ( A); Product ( A) is :
NH2 ¾ ¾¾
14.
H
(a) cyclopentane carboxyaldehyde
(c) 2-aminocyclohexene
15.
(b) cyclohexane-1, 2-diol
(d) cyclohex-2-enol
Choose the appropriate product for this reaction.
LiAlH 4 (excess)
CN ¾1.
¾¾¾¾¾
¾® product
2. H 3O +
(a)
CH2NH2
(b)
NH2
(c)
16.
(d)
OH
NH2
Which of the following product will be obtained in the given (consider minor product also)
Beckmann-type rearrangement ?
O
O
Me
(2)PCl 5, D
O
(a)
O
O
17.
O
H
N
Me
O
O
O
(c)
(1)NH 2OH,HCl
¾ ¾¾¾¾¾® product
(b)
O
N
H
Me
O
(d) all of these
N
Me
Deamination (or) diazotization of n-Bu–NH 2 with NaNO 2 HCl gives ......... isomeric butene.
(a) 2
(b) 3
(c) 4
(d) 5
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OH
O
O
||
||
Ac 2O
Ac 2O
¾ ¾¾
® P ¾ ¾¾
® Q Ac 2 O == CH 3 — C — O — C — CH 3
18.
NH2
P and Q respectively are :
O
||
OH
O—C—CH3
(b)
NH2
NH—C—CH3
||
O
O
||
C—O—CH3
NH2
OH
,
(d)
NH—C—CH3
||
O
NH—C—CH3
||
O
NH—C—CH3
||
O
NH—C—CH3
||
O
A nitrile X is treated with LiAIH 4 to obtain compound Y (C 2 H 7 N). In a separate reaction X is
hydrolyzed in an acid medium to obtain Z. The product obtained after mixing Y and Z will be
(a) CH 3 CONHCH 2 CH 3
(c) (CH 3 COO – )(CH 3 CH 2 NH +3 )
20.
NH—C—CH3
||
O
O
||
O—C—CH3
OH
,
(c)
O
||
C—O—CH3
,
,
(a)
19.
O
||
C—O—CH3
(b) CH 3 CH 2 CONHCH 2 CH 3
(d) (CH 3 CH 2 COO – )(CH 3 NH +2 )
The compound X(C 7 H 9 N) reacts with benzensulfonyl chloride to give Y(C 13 H 13 NO 2 S)
which is insoluble in alkali. The compound X is:
NH2
NHCH3
CH3
(a)
(b)
NH2
NH2
(c)
(d)
CH3
H3C
ANSWERS — LEVEL 1
1.
(c)
2.
(a)
3.
(d)
4.
(a)
5.
9.
(d)
10.
(b)
11.
(c)
12.
(c)
13.
17.
(b)
18.
(d)
19
(c)
20.
(a)
(b)
6.
(d)
14.
(b)
7.
(a)
15.
(d)
8.
(b)
(b)
16.
(d)
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492
Level - 2
1.
Five amine syntheses are outlined below. In each reaction box enter a single letter
designating the best reagent and conditions selected from the list at the bottom of the page.
CH2 – Br
First Step
A.
CH2 – CH2 – NH2
Second Step
O
O
B.
C – CH3
First Step
H
Second Step
CH2 – N
Third Step
C.
N–H
First Step
N
Second Step
NO2
First Step
D.
E.
CH2CH3
N(CH3)2
Second Step
First Step
Second Step
Br
(a) (i) LiAlH 4 in ether
(b) C 2 H 5 NH 2 (cat. H
(+ )
Third Step
N
Fourth Step
H
|
(ii) H 2 O & base
)
(c) NaCN in alcohol
(d) H 2 & Ni catalyst or H 2 & Pd catalyst
(e) NaN 3 in alcohol
(f) (CH 3 CO) 2 O & pyridine
(g) C 2 H 5 Br
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O
(h)
, Hr
(i) 2CH 3 I & pyridine
(j) KOH in H 2 O
ANSWERS — LEVEL 2
1.
A – c, a or c, d; B – b, d, f; C – h, d; D – d, i or a, i; E – e, a, h, a
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494
11
CARBENE AND NITRENE
Level - 1
OH
NH2
Br KOH
1.
2
¾ ¾¾¾
® product;
O
(a-hydroxy amide)
Product of this Hoffmann bromamide reaction is :
O
||
(a) Ph - C - CH 3
OH
(c) Ph – CH
(b) Ph – CHO
(d) Ph - CH 2 - NH 2
NO2
O
2.
O
NH2 ¾ KOBr
¾¾® ( A) ¾¾® ( B ). Compound (B) is :
HO
D
O
(a)
NH – C – H
(b)
C – NH
||
O
O
(c)
NH
O
CH3
(d) O
NH2
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495
O
||
CH2 – C – NH 2
KOBr
3.
¾ ¾¾® ( A); Product (A) is :
C – O – CH3
O
O
(a)
O
(b)
O
NH
O
O
(c)
NH
(d)
O
O
O
OH
Me
C
N
H SO
2
4
¾ ¾¾
¾
® Product and name of the reaction is :
4.
O
O
NH – C – Me
NH – C – Me
(Hoffmann
bromamide reaction)
(a)
(Beckmann
rearrangement)
(b)
CN
(c)
(Curtius reaction)
NH
(d) None of these
Br
3
2
5. ( X )C 4 H 7 OCl ¾ ¾¾
® C 4 H 9 ON ¾ ¾
¾
® CH 3 CH 2 CH 2 NH 2 ; Compound (X) is :
KOH
O
CH3
(a)
(b)
Cl
6.
(c)
Cl
OH
(d)
Cl
CHO
Which of the following will not give Hoffmann bromamide reaction ?
O
O
||
||
(a) CH 3 - C - NH 2
(b) Ph - C - NH 2
O
O
||
||
(d) Ph - C - NH - Ph
(c) CH 3 - C - NH - Br
OH
7.
CH3
O
||
C – Cl
OH
(1) NaOH
O; Reactant x is :
+ ( x) ¾¾¾®
r
(2) H
(a) CH 3 Cl
(b) CH 2 Cl 2
(c) CHCl 3
(d) CCl 4
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18
O –H
N
C
H SO
2
4
¾ ¾¾
¾
® ( A). Product (A) of the reaction is :
18
8.
H 2O
O18
||
(b) Ph - NH - C - P h
O
||
(a) Ph - NH - C - Ph
OH
|
(c) (Ph) 2 -C - NH 2
CH3
9.
..
(d) Ph - CH 2 - NH - Ph
Ph
Ph
C
C
H SO
2
4
¾ ¾¾
¾
® ( A),
N
..
OH
N
CH3
H SO
2
4
¾ ¾¾
¾
® (B)
OH
Product (A) & (B) respectively in the above reaction are :
O
O
||
||
(a) Ph - C - NH - CH 3 , Ph - C - NH - CH 3
O
O
||
||
(c) Ph - C - NH - CH 3 , CH 3 - C - NH - Ph
10.
O
O
||
||
(b) CH 3 - C - NH - Ph, CH 3 - C - NH - Ph
O
O
||
||
(d) CH 3 - C - NH - Ph, Ph - C - NH - CH 3
NBS ¾ KOBr
¾¾® (A) . Product (A) is :
O
O
OH
(a)
O
(b)
NH2
O
O
-
NH2
O
(c)
O
O
Ph
11.
NH
(d)
O
NaOBr
CH3
NH2
H
¾ ¾¾
¾®
( A) ; Product of the reaction is :
(major)
Ph
Ph
NH2
(a) CH3
H
(b) CH3
H
NH2
CH3
Ph O
(c) Ph
H
NH
-
C–O
(d) CH3
H
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OH
(1) CHCl 3 /NaOH
12.
¾¾¾¾¾¾®
( A)
r
(2)H
(Major)
OCH3
Product (A) is :
OH
O
(a)
13.
OH
OH
(b)
O
(c)
OH
O
OH
(d)
OCH3
OCH3
OCH3
O
||
R - C - NH 2 + xNaOH + Br 2 ¾¾® R - NH 2 + 2NaBr + Na 2 CO 3 + H 2 O
OH
OCH3 O
Number of moles of NaOH used in above Hoffmann bromamide reaction is :
(a) 3
(b) 4
(c) 5
(d) 6
R
14.
, Rate of reaction toward Beckmann rearrangement
C=N
H
when g = CH 3 CO -2 , Cl - CH 2 - CO 2- , Ph - SO 3(i)
15.
16.
(ii)
(iii)
(a) (i) > (ii) > (iii)
(b) (ii) > (i) > (iii)
(c) (iii) > (ii) > (i)
(d) (iii) > (i) > (ii)
When primary amine reacts with chloroform in ethanolic KOH, then product is :
(a) an isocyanide
(b) an aldehyde
(c) a cyanide
(d) an alcohol
The reaction of chloroform with alcoholic KOH and p-toluidine forms :
(a) H3C
CN
(c)
17.
(b) H3C
NC
(d) H3C
NHCHCl2
What is the product (Q) of the following reaction ?
CHFBrI
t- BuOK
¾ ¾¾
¾®(Q )
Cl
Cl
(a)
(b)
(c)
(d)
Cl
F
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498
CHBr2
NaOH, 50%
D
18.
¾ ¾¾¾¾® ( A) ; Product (A) is :
Br
(a)
(b)
(c)
Br
Br
19.
(d)
Br
Which of the following reaction, does not give chloro benzene as a product ?
CHCl , HO -
(a)
3
¾ ¾¾¾¾
®
(c)
2
¾ ¾¾¾¾¾
®
CHBr Cl, HO -
CHBrCl , HO -
(b)
2
¾ ¾¾¾¾
¾®
(d)
¾ ¾¾¾¾¾®
CHFClBr, HO -
(3 mole)CH I
22
¾ ¾¾¾¾
¾® ( A) ; Compound (A) is :
20.
Zn Cu
(a)
(b)
(c)
(d)
NH2
21.
+ CHCl 3 + xKOH ¾®
NººC
x = moles of KOH consumed is :
(a) 1
22.
(b) 2
(c) 3
(d) 4
Heating the acyl azide in dry toluene under reflux for 3-hours give a 90% yield for a
heterocyclic product. Identify the product (A).
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O
C—N3
heat
¾ ¾¾® ( A)
toluene
NH2
H
90%
O
N
(a)
O
(b)
N
H
N—H
N
H
O
NH
— NH 2
(c)
NH2
(d)
C
O
H
C == C
Br
Å–
K O C(CH )
3 3
¾ ¾¾¾¾
¾® ( A)
23.
Heat
Br
14
C == C
(a)
C ºº C
(c)
C ºº C
Br
(b)
C ºº C
(d)
C ºº C
Br
Br
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500
CO2H
24.
(1) CH 2N 2
(A) (de-colourises Br 2 water)
OH ¾¾¾¾¾¾¾®
+
HO
( 2) acetone H
( 3)Ac 2O, Acetic anhydride
OH
Product (A) of the above reaction is :
CO2CH3
CO2CH3
OAc
O
(a)
O
O C
OAc
CO2Ac
O
CH3 CH
3
CO2H
OMe
(c) O
25.
(b)
(d) AcO
O
OMe
OMe
A rather interesting example of the Wolff rearrangement with 2-diazocyclohexanone in
methanol is given below. Identify the major product :
O
N2
CH3OH/light
O
OCH3
(a)
(b)
CO2CH3
O
O
O
(c)
26.
(d)
C¾O¾H
The orbital picture of a singlet carbene (: CH 2 ) can be drawn as :
p
H
C
(a)
H
p
H
C
(b)
sp2
H
sp2
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py
pz
C
(c)
H
(d) none of these
H
27. The orbital picture of a triplet carbene can be drawn as :
p
H
C
(a)
p
H
C
(b)
H
H
sp2
py
sp2
pz
H
C
(c)
(d) none of these
H
CHCl
CHCl
KOH
KOH
3
3
¾ ¾¾
¾
® ( A) ¾ ¾¾
¾
® ( B ) ; Product (B) is :
28.
Cl
Cl
Cl
(a)
(b)
Cl
Cl
Cl
Cl
(c)
(d)
Cl
29.
?
Select the suitable reagent for above conversion.
(a) CH 2 N 2 / D
(c) H 2 C == CH 2
(b) CBr 4 / RLi
(d) t-BuOK
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HO
30.
CH2I2 (2 mole)
HO
Zn (Cu)
A
(97%)
Product (A) will be :
HO
(c) HO
31.
HO
(b) HO
(a) HO
OCH3
(d) CH3O
HO
The major product formed in the following reaction is
Me
Me
+ :CH 2 (singlet) ¾¾®
H
H
Me
Me
Me
(a)
(b)
H
H
H
Me
H
Me
CH2CH3
(c) 50 : 50 mixture of above two compounds(d)
H
H
H
Br
Br
32.
O
H
O
To carry out above conversion reagent used in decreasing order.
(a) Na liq.NH 3 , CHBr 3 NaOH ( D )
(c) Na liq.NH 3 , CHCl 3 NaOH
(b) H 2 Pd - CaCO 3 , CHBr 3 NaOH ( D )
(d) H 2 Pd - CaCO 3 , CHCl 3 NaOH
O
2
CH2 ¾ Br
¾
¾
® (A) + CHBr 3 ¯
KOH
33.
O
Product (A) of the reaction is :
CO2H
(a)
(b)
CO2H
–
CO2
CO2H
(c)
C – CH3
||
O
CH3
(d)
CO2–
CO2H
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C
N
(1) HO - (1 mole)
34.
¾ ¾¾¾¾¾
¾® (A); Product (A) is :
(2) HO , Br2
NO2
–
CO2
NO2
NH2
Br
(a)
(b)
(c)
(d)
NO2
NH2
NO2
NO2
O
NH
35.
NaOCl
¾ ¾¾
¾® ( X ) ; Product X will be :
H2O
(80%)
NO2 O
CO2H
NH2
(a)
(b)
NH2
CO2H
NO2
NO2
CO2H
NH2
(c)
(d)
CO2H
NO2
CO2H
NO2
36.
CH 2N 2 D
CH 3 — CH 2 — CH 2 — CH 2 — CH 3 ¾¾¾¾¾® Products
Which of the following product(s) is/are can be obtained in the above reaction.
(a) Isopentane
O
37.
CH3—C—NH2
(b) 3-Methyl hexane (c) n-Pentane
KOBr
LiAlH4
(a) Identical
(d) 3-Methyl pentane
(A) Relation between ( A) & ( B ) is :
(B)
(b) Functional isomer (c) Homologous
(d) Positional isomers
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38.
If we use pyrene (CCl 4 ) in the Riemer-Tiemann reaction in place of chloroform, the product
formed is :
(a) Salicylaldehyde
39.
(b) Phenolphthalein (c) Salicylic acid
When ethyl amine is heated with chloroform and alcoholic KOH, a compound with offensive
smell is obtained. This compound is :
(a) A secondary amine
(c) A cyanide
40.
(d) Cyclohexanol
(b) An isocyanide
(d) An acid
Which of the following species would not be involved in the Hoffmann rearrangement shown
below ?
O
Br2, NaOH, H 2O
NH2
¾ ¾¾¾¾¾
®
NH2
O
(a)
NHBr
O
(b)
s
N—Br
N==C==O
(c)
41.
(d) All of the above are involved in the reaction.
In which of the following reactions migration of alkyl group from carbon to oxygen is
observed ?
(a) Pinacol-pinacolone rearrangement
(b) Bayer-villiger oxidation.
(c) Prepration of phenol from cumene hydroperoxide.
(d) Both (b) & (c)
ANSWERS — LEVEL 1
1.
(b)
2.
(b)
3.
(c)
4.
(b)
5.
(a)
6.
(d)
7.
(c)
8.
(b)
9.
(c)
10.
(b)
11.
(a)
12.
(a)
13.
(b)
14.
(c)
15.
(a)
16.
(b)
17.
(d)
18.
(a)
19.
(d)
20.
(a)
21.
(c)
22.
(a)
23.
(b)
24.
(b)
25.
(a)
27.
(c)
28.
(c)
29.
(a)
30.
(b)
31.
(a)
32.
(b)
(c)
35.
(b)
36.
(d)
37.
(c)
38.
(c)
39.
(b)
40.
(d)
(a)
26.
33.
(c)
34.
41.
(d)
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505
Level - 2
1. Comprehension
Hoffmann bromamide reaction involves conversion of a carboxylic acid amide into an amine
with a loss of a carbon atom on treatment with aqueous sodium hypobromite. Thus
Hoffmann result in shortening of a carbon chain.
O
||
Br2
¾® R - NH 2 + NaBr + Na 2 CO 3
R - C - NH 2 ¾ ¾¾
NaOH
Mechanism of the reaction is :
O–
O
R – C – NH2
NaOH
R – C = NH + Br — Br
O
R – C – NH – Br
–
HO
O
Na2CO3 + R–NH2
A.
H2O
O = C= N–R
–
R – C – N – Br
Number of moles of NaOH consumed in above reaction.
(a) 1
(b) 2
(c) 3
(d) 4
O
C – NH2
B.
KOH
(a) Ph - NH 2
C.
Br2
¾¾
¾® ( A) ; Product (A) :
(Major)
(b) Ph - CH 2 - NH 2
(c) Ph - NH - CH 3
(d) Ph – N
Which of the following will not give Hoffmann bromamide reaction.
O
O
||
C – NH – Br
(a) CH 3 - C - NH 2
(b)
O
O
(c)
C – NH2
(d)
CH3
CH3
C – NH – CH 3
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506
O
NH ¾ KOBr
¾¾® ( A), Product (A) is :
D.
O
NH2
OK
O
(a)
NH — CH3
OH
O
(b)
(c)
NH2
NH2
(d) None of these
2. Comprehension
Given is mechanism of Beckmann rearrangement.
H+
C == N
OH
CH3
(I)
C == N
CH3
O
(II)
O—H
H
CH3 — C — NH — Ph
CH3 — C == N —
H2O (III)
(IV)
CH3 — C == N —
OH
A.
Rate determining step in Beckmann rearrangement :
(a) I
B.
(b) II
(c) III
(d) IV
CH3
C == N
Ph
OH
On treatment H 2 SO 4 followed by hydrolysis in acidic medium above compound gives.
(a) CH 3 - CO 2 H, Ph - NH 2
(c) Ph - CH 2 - NH 2 + Ph - CO 2 H
C.
(b) CH 3 - NH 2 ,Ph - CO 2 H
(d) Ph - CO 2 H + CH 3 - CO 2 H
Which of the following reagent cannot used in Beckmann rearrangement ?
(a) TsOH
(b) R - SO 2 Cl
(c) BF3
(d) Ph - Li
OH
C == N
D.
PCl
D
5
¾ ¾¾
® ( A);
CH3
Product ( A) of the above reaction is :
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O
O
C — NH
(a)
C — NH
(b)
CH3
CH3
O
O
3.
C — NH
CH3 (d) CH3
C — NH
(c) CH3
Match the column I and II.
Column (I)
Column (II)
Cl
(a)
aq. KOH
H+
CHCl
KOH
3
¾ ¾¾¾®( A) ¾ ¾
¾® ( B ) ¾ ¾¾
¾
® (C )
D
(p)
D.B.E. = even for product
(Double bond equivalent)
(q)
D.B.E. = odd for product
OH
(b)
H+
CHCl
KOH
3
¾¾
¾® ( A) ¾ ¾¾
¾
® ( B)
D
(c)
(d)
CHCl
KOH
CHCl
KOH
3
3
¾ ¾¾
¾
®( A) ¾ ¾¾
¾
® ( B)
H+
N
|
H
CHFClBr
¾® ( A) ¾ ¾¾¾® ( B )
OH ¾ ¾
D
D
(r) Ring expansion takes place
(s)
Carbene will formed
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4. Match the column I and II.
Column (I)
Column (II)
CHCl
KOH
3
¾ ¾ ¾¾
®
(a)
(p)
Reimer Tiemann reaction
(q)
Reimer Tiemann expansion
(or) Abnormal RNT reaction
(r)
Simman-smith reaction.
(s)
Increase in carbon takes place
OH
(b)
CHCl
KOH
3
¾ ¾ ¾¾
®
CCl COONa
(c)
3
¾ ¾¾¾¾
®
D
OH
(d)
CH I +Zn
22
¾¾¾
¾¾®
D
5. Match the column I and II.
Column (I)
Column (II)
NH 3
2 ® ¾ ¾¾
CO2H ¾ SOCl
¾¾
¾
®
(a)
HNO
KOBr
(p)
Aromatic compound will formed
(q)
Migration take place from carbon to
electron deficient nitrogen
(r)
Carbene will formed in this reaction
(s)
N 2 will evolve.
2®
¾¾¾
¾® ¾ ¾ ¾¾
(b)
C
|
Cl
hv
C C
Q
t -BuO K
(c)
f-C ºC -f
(A)
Å
f - CHCl 2 ¾ ¾ ¾ ¾ ¾
¾® ( A )
AlCl
3 ® (C )
¾¾¾¾
¾® ( B ) ¾ ¾ ¾
¾
O2N
(d)
N
||
N
NO2
O
||
C – NH2
KOBr
¾¾¾
¾®
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6.
Match the column I and II:
(a)
(b)
(c)
(d)
Column (I)
Column (II)
Reaction
Intermediate
CHCl 3 + KOH ¾¾®
D
Br
Br
Ph -Li
D
¾¾¾
¾®
Cl O
| ||
Na
¾®
Cl – C – C – OH¾ ¾
D
|
Cl
OH
H+
D
¾¾
¾®
(p)
Carbocation
(q)
Carbanion
(r)
Free radical
(s)
Carbene
7. Matrix :
Column (I)
Column (II)
Reaction
Product
F
(a)
CHCl
KOH, D
3®
¾ ¾ ¾¾
(p)
Cl
(b)
CHFClBr
KOH, D
¾¾¾¾
¾®
(q)
Br
(c)
¾ ¾ ¾2¾
¾®
CHCl Br
KOH, D
(r)
(d)
¾ ¾ ¾2¾®
CHBr Cl
KOH, D
(s)
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8. Comprehension
1. Consider the given reaction for preparation of alkyne. (Fritsch reaction).
dQ
Ph–Li
(Acid-base)
H
C=C
Cl
Ph
Q
C=C
Ph
r.d.s
Cl
¾ ¾¾® Ph–C º C – Ph
Anti group will migrate because of less steric hindrance.
H
14
C=C
Å Q
KOC(CH )
Br
A.
3 3
¾ ¾¾¾¾
¾® ( A) ; Major product (A) is :
D
(major)
Br
14
(a)
Br
CºC
(c) Ph – C º C 14 – Ph
C
B.
H
D
(b)
(c)
(d)
(a)
CH3O
Br
+ K Å O Q C(CH 3 ) 3 ¾¾® ( A), product (A) is :
+
Br
(a)
CH3O
CºC
(d) Ph – C º C – Ph
C. Rate of reaction when the halide ion:
(a) I Q > Cl Q > Br Q > F Q
(c) F Q > Cl Q > Br Q > I Q
D.
14
(b)
*
C
H
Br
* Br
t -BuOK
D
¾ ¾¾¾®
(b) I Q > Br Q > Cl Q > F Q
(d) F Q > Br Q > Cl Q > I Q
(A) (Major) , Product (A) is : (C* = C14)
CH3O
*
(b)
Br
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511
CH3O
*
(c)
(d)
CH3O
* Br
Br
9. Comprehension
Wolff rearrangement
When a-Diazoketones are photo-irradiated or heated at high temperature or reacted with
silver oxide or silver salts at room temperature, they loose nitrogen and rearrange to form
ketene.
The ketenes reacts rapidly with water, alcohol and amines. Therefore, the reactions called
Wolff-rearrangement.
O
||
2O
C – CHN2 ¾ Ag
¾¾
® N2 + Ph – CH = C = O
|
| CH - NH
H O
2
¯ 2
¯ 3
Ph - CH 2 - CO 2H
Ph - CH 2 - C - NH - CH 3
||
O
O
||
Ag 2O
A. Ph - C - CHN 2 ¾ ¾¾
® ( A), Product (A) is :
H 2O
14
14
14
(a) Ph - CH 2 - CO 2H
(b) Ph - CH 2 - CO 2H
14
(c) Ph - CO 2H
Q
O
N
Å
N
*
(d) Ph - CO 2H
CH OH
hv
3
¾ ¾¾
¾® ( A) (Major), Product (A) is :
B.
14
*
(C = C)
O
*
OCH3
(a)
(c)
(b)
O
||
C – OCH3
*
*
O
||
C – OCH3
(d)
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O
||
2O
C – C – CHN2 + CH OH ¾ Ag
¾¾
® Major product of the reaction is :
3
H
C. CH3
Et
O
||
C – C – OCH3
Et
(a) CH3
(b) CH3
Et
H
O
||
C – C – OCH3
CH3
(c)
H
O
||
C – C – OCH3
H
(d) None of these
Et
O
||
C – CHN2
Ag O
2
¾ ¾¾
® ( A) (Major) , Product (A) is :
D.
C – CHN2
||
O
NH 3
O
||
C – NH2
(a)
O
||
CH2 – C – NH2
(b)
C – NH2
||
O
O
||
C – NH2
(c)
CH2– C – NH2
||
O
CH2 – CONH2
(d)
C – NH2
||
O
CH2 – CONH2
N2
||
E. Ph - C - CH 2OCH 3 ¾¾® ( A) 90% , product (A) is :
D
(a) Ph – CH = CH – OH
(c) CH 3 – CH = CH – O – PH
(b) Ph – CH = CH – OCH 3
(d) CH 3 – CH = CH – OH
hv
F.
¾ ¾¾¾® ( A) , Product (A) is :
CH 3OH
O
N2
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513
(a)
(b)
CO2CH3
O
(c)
(d)
CO2CH3
CO2CH3
O
O
||
Ag 2O
G. HO - CH 2 - CH 2 - CH 2 - C - CHN 2 ¾ ¾¾
® ( A) , Product (A) is :
D
O
(a)
O
O
O
O
O
O
(b)
O
(c)
O
(d)
ANSWERS — LEVEL 2
1.
A – d, ; B – a; C – d, ; D – a,
2.
A – b; B – b; C – d; D – b
3.
a – p, r, s; b – q, r, s; c – q, r, s; d – p, r, s
4.
a – q, s; b – p, s; c – s; d – r, s
5.
a – p, q, s; b ® p, r, s ; c – p, r ; d – p,q
6.
a – q, s; b – q, s; c – q, s; d – p
7.
a – q; b – p; c – q; d – q
8.
A – a; B – c; C – b; D – b
9.
A – b; B – c; C – d; D – b; E – b; F – b; G – c
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12
AROMATIC COMPOUNDS
Level - 1
O
||
NH – C – CH3
CH3
1.
A
C
B
Identify the position where electrophilic aromatic substitution (EAS) is most favourable.
(a) A
(b) B
(c) C
(d) A and C
NO2
CH3
Cl
2.
(a)
(b)
(c)
(d)
Correct order of rate of EAS (electrophilic aromatic substitution) is :
(a) c > b > a > d
(b) c > d > a > b
(c) a > b > c > d
(d) c > d > b > a
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N
+ Ar — N ºº N Å Cl - ¾®
3.
4.
N
N = N - Ar
Above (C—N) coupling reaction take place at :
(a) low pH
(b) Intermediate pH
(c) high pH
(d) any pH
Which of the following has the lowest heat of combustion ?
(a)
5.
(b)
(c)
(d)
The product obtained from the reaction is :
Br
CH2Cl + NaCN
ethanol
(a) Br
CH2CN
(b) Br
CH2Cl
(c) NC
CH2CN
(d) Br
CH2Cl
CN
CO
+
6.
CO
1.SOCl 2
AlCl 3
Zn— Hg, HCl, heat
O ¾1.
¾¾¾
® A ¾ ¾¾¾¾¾¾® B ¾ ¾¾¾® C.
2. AlCl 3
3. H 3O +
2. H 3O +
The end product (C) is :
O
(a)
(b)
O
O
O
O
C — C6H5
C
(c)
(d)
C — C6H5
COOH
O
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7. How many benzylic hydrogens are present in the hydrocarbon shown below ?
(a) 3
(b) 4
(c) 5
8. The major product formed in the reaction is :
(d) 6
(e) 8
conc. H2SO4
+ HNO3
NO2
NO2
(a)
(b)
(c)
(d)
NO2
NO2
9. The major product formed in the reaction is :
O
Conc. HNO /conc. H SO
3
2
4
¾ ¾¾¾¾¾¾¾¾
¾
®
C–O
(mononitration)
O
O
C–O
(a)
(b) O2N
C–O
O2N
O
(c)
O
(d)
C–O
C–O
NO2
NO2
10.
Increasing order of rate of reaction with HNO 3 H 2 SO 4 is :
O
O
O
O
O
O
(i)
(a) iii < ii< i
O
O
O
(ii)
(b) ii < iii < i
O
O
O
(iii)
(c) i < iii < ii
(d) i < ii < iii
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11.
Increasing order of rate of reaction with Br 2 AlCl 3 is :
OH
O
OH
OH
O
(i)
12.
(ii)
(iv)
(iii)
(a) iii < i < ii < iv (b) iv < ii < i < iii (c) ii < iv < iii < i (d) iv < ii < iii < i
Increasing order of equilibrium constant for the formation of a hydrate is :
O
O
O
O
H3CO
O2N
CH3O
(i)
(iii)
(ii)
(iv)
(a) i < ii < iii < iv (b) iv < ii < i < iii (c) ii < iv < iii < i (d) iv < ii < iii < i
13. Rank the following reactions A, B and C in order of increasing rate,
Me
Me
Me
Me
SO3/H2SO4
(A)
(B)
SO3/H2SO4
SO3H
SO3H
NO2
(C)
NO2
SO3/H2SO4
SO3H
14.
(a) B > A > C
(b) B > C > A
(c) A > B > C
(d) A > C > B
Rank in order of increasing rate of reaction towards EAS with bromine in the presence of
FeBr 3 .
(A)
(a) B < A < C
(c) A < B < C
(B)
(C)
(b) B < C < A
(d) A < C < B
15.
Identify the position where E.A.S. can take place.
(a) 1
(b) 2
(c) 3
(d) 4
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H+
D
HNO
D
3
¾¾
¾® ( A) ¾ ¾¾
¾
® ( B ).
16.
Product (B) in the above reactions is:
NO2
(a)
(b)
(c)
(d)
NO2
NO2
NO2
1
2
O
17.
NH
3
Sulphonation is most favourable at the carbon number... .
4
(a) 1
(b) 2
(c) 3
(d) 4
18. Arrange the following in decreasing order of reactivity towards EAS (electrophilic aromatic
substitution)
CH3
CD3
CT3
(b)
(a)
(a) a > b > c
(b) c > b > a
(c)
(c) a > c > b
(d) c > a > b
19.
(a)
(b)
(c)
(d)
Decreasing order of rate of electrophilic aromatic substitution is :
(a) a > b > c > d
(b) a > c > b > d
(c) b > a > c > d
(d) b > c > a > d
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20. Arrange the following in increasing order of rate of Nitration:
D
NO2
Me
D
D
Cl
D
D
D
(a)
(c)
(b)
(e)
(d)
(a) b < c < a < d < e
(c) d < a = c < e < b
(b) d < e < a = c < b
(d) a < c < b < e < d
Me
Me
Me
H
H
H
D
D
D
21.
(a)
(c)
(b)
The rate of nitration will be:
(a) a > b > c
(b) a > c > b
22. The major product of the reaction is
(c) a = b = c
(d) c > a > b
1. CH COCl/AlCl
3
3
¾ ¾¾¾¾¾
¾
® Product.
2. H 2O
O | CH3
|
C
(a) CH3 – C
(b)
O
(c)
(d)
C
O
CH3
||
C
||
O
CH3
23. Arrange in their decreasing order of rate of electrophilic aromatic substitution :
(i)
(a) i > ii > iii
(b) iii > ii > i
(ii)
(iii)
(c) iii > i > ii
(d) i > iii > ii
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Cl
Cl
24.
+ HO - ¾® ( A) ; Product (A) of the given reaction is :
Cl
(4 mole)
(major)
Cl
(2 mole)
Cl
Cl
O
Cl
(a)
Cl
O
Cl
Cl
O
Cl
(b)
O
Cl
Cl
Cl
O
Cl
Cl
Cl
O
(c)
(d)
O
O
Cl
25.
Cl
Cl
Cl
In which of the following compound electrophilic aromatic substitution take place in phenyl
ring present in left hand side ?
O
O
C—O
(a)
C — NH
(b)
O
CH2 — O
(c)
H SO
2
4
+ A ¾ ¾¾
¾
®
26.
O
O
(b)
(c)
O
(d)
|
O
27.
; Reactant (A) is :
|
O
(a)
CH2 — C
(d)
CO2H
CO2H
Which of the following compounds is the slowest to react with nitrosonium ion (NO + ) ?
CH3
O
OMe
(a)
(b)
(c)
(d)
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O
||
O
||
(CH ) CH –C – Cl
Clemmensen
reduction
CH –C – Cl
NaCN
AlCl 3
H 2SO 4
Red P + HI
3
3 2
¾ ¾¾¾¾¾
¾® ¾ ¾¾¾¾
¾® ¾ ¾¾¾¾
®¾ ¾¾¾® ¾ ¾¾¾
¾®(Ibuprofen)
Å
28.
AlCl 3
H 3O
Ibuprofen is :
CH 3
|
CH — CO 2 H
(a) CH 3 — CH 2
(b) CH 3 — CH — CH 2
|
CH 3
CH — CO 2 H
|
CH 3
COOH
CH3 – CH - CH3
(c)
(d)
O
CH2 - C
29.
O
AlCl3
CH2 - CH - C
O
What is the major product of above Friedel-Craft reaction ?
O
O
CO2H
(a)
(b)
CO2H
O
O
CO2H
(c)
30.
(d)
CO2H
What combination of acid chloride or anhydride and arene would you choose to prepare
given compound ?
C — CH2 — CH2 — CO2H
O
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O
(a)
O
+ Cl — C — CH2 — CH — C — Cl
AlCl3
CH3
O
(b)
+
AlCl3
O
O
O
(c)
+
AlCl3
O
O
O
(d)
31.
AlCl3
+
O
In the given conversion best yield will obtained with :
O
(A)
C
CH3
(B)
O
O
||
(a) A = CH 3 — C — Cl, AlCl 3 , B = Zn(Hg), HCl
O
||
(b) A = Zn(Hg),HCl, B = CH 3 — C — Cl, AlCl 3
(c) A = CH 3 — CH 2 — Cl, AlCl 3 , B = Zn(Hg), HCl
(d) A = NH 2 — NH 2 HO - ,D , B = CH 3 — CH 2 — Cl, AlCl 3
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32.
Rank the following in order of decreasing rate of reaction with alkoxide ion (CH 3 CH 2 O - ) in
a nucleophilic aromatic substitution reaction :
Br
Br
Br
Br
NO2
NO2
NO2
NO2
NO2
1
2
(a) 3 > 4 > 1 > 2
33.
NO2
3
(b) 3 > 4 > 2 > 1
4
(c) 2 > 1 > 4 > 3
Identify the principal organic product of the following reaction.
F
+ NaSCH 3 ¾® product
Br
O2N
F
(a)
SCH3
CH3S
Br
CH3S
F
O2N
Br
(b)
Br
O2N
F
(c)
34.
(d) 4 > 3 > 2 > 1
(d)
O2 N
SCH3
Which position will be attacked most rapidly by the nitronium ion ( – NO 2 )+ when the
compound undergoes nitration with HNO 3 H 2 SO 4 :
O
A
B
C
D
OCH3
(a) A
NH2
(b) B
Conc.H SO
(c) C
(d) D
Br H O
excess
2
4
2
2
¾ ¾¾¾¾
¾
®( X ) ¾ ¾¾¾
®(Y ): Product (Y) of this reaction is :
35.
NH2
NH2
Br
Br
SO 3H
(a)
Br
(b)
SO3H
Br
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NH2
NH2
Br
Br
Br
(c)
(d)
SO3H
Br
36.
Br
Br
All the hydrocarbons shown are very weak acids. One, however, is far more acidic than the
others. Which one is the strongest acid ?
(a)
(b)
(c)
(d)
O
+
37.
O
1. AlCl3
(A)
2. SOCl2
3. NaN3
(B)
4. MeOH
5. LiAlH4
(C)
6. NaH,
8. D
7.
O
(D)
CF3
Cl
Product (D) in above sequence is :
CF3
CF3
O
O
(a)
NH — CH3
(b)
OH
OH
N — CH3
(c)
38.
NH
(d)
CH3
CF3
The action of bromine water (excess) on salicylic acid results in the formation of :
Br
COOH
Br
COOH
(a)
OH
(b)
OH
Br
Br
(c)
OH
Br
Br
COOH
(d)
Br
Br
Br
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39.
What is the correct order of o p ratio when E + attacks the following system ?
PhF
PhCl
PhBr
PhI
(a) A < B < C < D
(b) A = B = C = D
(c) D < C < B < A
(d) D < B < A < C
A
40.
B
C
D
How many products are capable of beings formed from toluene in each of following reaction ?
CH3
O3
HN
SO 4
H 2 °)
(40
HNO
3
H2 S
O4
(80°
)
HNO3
H2SO4
(110°)
Mono-nitration
(A)
Di-nitration
(B)
Tri-nitration
(C)
(a) A = 3 , B = 6 , C = 8
(c) A = 3 , B = 6 , C = 10
41.
(b) A = 3 , B = 6 , C = 6
(d) A = 3 , B = 4 , C = 6
Nitration takes place at the which position of the given compound ?
CMe3
D
A
C
B
(a) A
(c) C
CHMe2
(b) B
(d) D
CH2 — CO2H
Ac2O
42.
D
CO2H
? , Indentify the product.
CH2 — CCl2Ac
(a)
CH2 — CO2H
(b)
CO2Ac
CO2H
O
O
(c)
(d)
O
O
O
O
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O
43.
Cl – C
Cl
(A) ; Unknown (A) is :
AlCl3
O
C=O
(a)
(b)
C=O
|
Cl
(d) Ph -C - Ph
Cl
Cl
H2SO4
+
44.
(1) NBS
( A)
D
||
(c)
C=O
(2) alc. KOH
RCO3H
( B)
OH
O
(a)
O
(b)
( C) . Product (C) is :
O
(c)
(d)
OH
Ph
Ph
45. The reaction of toluene with chlorine in the presence of light gives :
CH3
Cl
CH3
Cl
(a)
(b)
Cl
46.
+
(a)
(a)
(c)
(d)
Cl
O
AlCl3
Cl
H2O
(b)
D
(b)
(A)
NH2 – NH2
HO– , D
(B), Product (B) in this reaction is :
(c)
HF
+
47.
CH3
CH2Cl
Cl
CH2 – OH
(d)
OH
Suitable product of this reaction is :
(c)
(d)
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Me
NaSH
48.
A; Product (A) of the reaction is :
Cl
SH
CH2 – SH
(a)
(b) no reaction
SH
(c)
(d)
CH3
Cl
Cl
NH2
Br2
49.
H2O
(A)
(i) NaNO2/HCl
(ii) H3PO2
( B) , Product (B) in this reaction is :
Br
Br
Br
Br
(a)
Br
(b)
Br
Br
Br
(c)
Br
(d)
Br
Cl
Na2S
50. 2
(A), Product (A) in this reaction is :
NO2
NO2
SH
Cl
(a)
(b)
S
(c)
NO2
(d)
NO2
SH
S
NO2
NO2
O–H
NH2
NaNO2/HCl
51.
(A)
(B),
(mild basic medium) (Major)
Product (B) of this reaction is :
CH3
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CH3
OH
(a)
(b)
N == N
OH
N == N - Ph
OH
(c)
CH3
(d)
CH3
N == N
Ph
O–H
HNO3/H2SO4
52.
(A)
+
(more volatile)
( B)
(less volatile)
Product (A) of the above reaction is :
OH
OH
OH
NO2
NO2
(a)
(b)
(c)
(d)
NO2
NO2
NH2
2ICl
53.
+ 2HCl; Major product ( x) in this reaction is :
x
(56 – 63%)
NO2
NH2
NH2
NH2
I
(a)
I
(b)
I
NO2
NO2
HNO3
H2SO4
54.
I
I
(a) 2
(a) CF3 CO 3 H
(d)
NO2
I
NO2
(c) 4
(d) 5
NO2
?
55.
I
, van’t-Hoff factor (i) for this reaction is :
(b) 3
NH2
(c)
NO2
NH2
I
, the missing reagent is :
(b) H 2 SO 4
(c) LAH
(d) NaBH 4
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529
X
OCH3
CH3O–
56.
NO2
NO2
above reaction is an example of Nucleophilic aromatic substitution. Which of the following
halide (-X) is most readily replaced.
(a) – F
(b) – Cl
(c) – Br
(d) – I
57. When comparing the hydrogenation of benzene with that of a hypothetical 1, 3,
5-cyclohexatriene, benzene ________ than the cyclohexatriene.
(a) absorbs 152 kJ /mol more heat
(b) gives off 152 kJ/mol more heat
(c) absorbs 152kJ /mol less heat
(d) gives off 152 kJ/mol less heat
58. Which of the following hydrogens is most easily abstracted on reaction with bromine free
radicals, Br• ?
CH3
CH3CH2
(a) (b)
(c)
(d)
(a) a
(b) b
(c) c
(d) d
59. The electrophilic aromatic substitution proceeds through a :
(a) free radical
(b) sigma complex
(c) benzyne
(d) carbene
60. Which of the following substitution of benzene is ortho-para in electrophilic substitution and
ortho-para in nucleophilic substitution ?
(a) – NO 2
(b) – NO
(c) – SO 3 H
(d) – SO 2 Me
61. The number of possible isomers of dichloronitrobenzene is :
(a) 3
(b) 4
(c) 6
(d) 8
62. Which of the following is not an aromatic compound ?
(a)
(b)
(c)
(d)
63. Consider the following sequence of reactions.
COOH
1. SOCl2
Zn-Hg
¾¾¾¾¾®
A ¾¾¾¾®
B
Conc. HCl
CH2C6H5
2. anhyd. AlCl3
The end product ( B ) is:
O
(a)
(b)
CHO
(c)
(d)
CH2C6H5
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530
AlCl
3
64. Ph - NO 2 + Et - Cl ¾ ¾¾
® ( A), Product (A) of the given reaction is :
NO2
(a) Ph – NH – Et
(b) no–reaction
(c)
NO2
(d)
Et
Et
65. In nitration of benzene by mixed acid the rate of reaction will be :
(a) C 6 H 6 = C 6 D 6 = C 6 T6
(b) C 6 H 6 > C 6 D 6 > C 6 T6
(c) C 6 H 6 = C 6 D 6 > C 6 T6
(d) C 6 H 6 < C 6 D 6 < C 6 T6
NH2
H2SO5
66.
(A)
Ph – CH2CN
EtO–/D
(B) ; Product (B) is :
(a) Ph - N = C - CN
(b) Ph - N = C - Ph
|
Ph
(c) Ph - N = N - Ph
(d) Ph - CH = CH - Ph
67. Which of the following ring compounds obeys Huckel's rule ?
(a) C 4 H -41
(b) C 4 H +41
(c) C 4 H -2
4
(d) C 4 H 4
68. Nitration of which of the following reactant gives maximum % of meta product (using
HNO 3 H 2 SO 4 ) ?
(a) Toluene
(b) Aniline
(c) Benzene
(d) Isopropyl benzene
Br
Ph
Ph
2AgBF
4
¾ ¾¾¾
® ( x) 2BF4- ; compound (x) will be :
69.
Ph
Ph
Br
Ph
Ph
(a)
(b)
+2
Ph
Ph
Ph
Ph
(c)
–2
Ph
Ph
Ph
Ph
Ph
–1
(d)
+1
Ph
Ph
Ph
Ph
Ph
-
O
70.
(1) CO2
(2) HÅ
(A)
Which of the following is true statement about the reaction ?
(a) Ortho isomer is major if PhONa is used
(b) Para isomer is major if PhOK is used
(c) Product formed is further used for preparation of drug aspirin
(d) All of these
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531
71. Two benzyne intermediates are likely to be formed equally. Reaction with amide ion can
occur in two different directions with each benzyne, giving three possible products. They are
formed in a 1 : 2 : 1 ratio. Asterisk (*) refers to 14 C.
*
NaNH2
Cl
(A) Product major; product ( A) is :
NH3
*
*
NH2
(a)
NH2
*
(b)
NH2
(c)
NH2
(d)
*
72. Which one of the following undergoes nucleophilic aromatic substitution at the fastest rate ?
Cl
Cl
Cl
Cl
(a)
(b)
(c)
(d)
Cl
NO2
CH3
Br
73. For the reaction ;
? ¾¾®
OCH3
; the best combination of reactants is :
NO2
(a) C 6 H 5 Br + HNO 3 , H 2 SO 4
(b) C 6 H 5 Br + H 2 SO 4 , heat
(c) C 6 H 5 NO 2 + Br 2 , FeBr 3
(d) C 6 H 5 NO 2 + HBr
74. The action of AlCl 3 in Friedel Craft’s reaction is:
(a) to absorb HCl
(b) to release HCl
(c) to produce electrophile
(d) to produce nucleophile
75. n-Butylbenzene on oxidation with hot alkanine KMnO 4 gives :
(a) benzoic acid
(b) butanoic acid
(c) benzyl alcohol
(d) benzaldehyde
76. Which sequence of steps describes the best synthesis of 2-phenylpropene ?
(a) Benzene + 2-chloropropene , AlCl 3
(b) 1. Benzaldehyde (C 6 H 5 CH = O) + CH 3 CH 2 MgBr , diethyl ether
2. H 3 O +
3. H 2 SO 4 , heat
(c) 1. Bromobenzene + Mg, diethyl ether
3. H 3 O +
2. Propanal (CH 3 CH 2 CH = O)
4. H 2 SO 4 , heat
(d) 1. Bromobenzene + Mg, diethyl ether
3. H 3 O +
2. Acetone [(CH 3 ) 2 C = O]
4. H 2 SO 4 , heat
77. What are the products of the following reaction ?
excess HBr
OCH2CH2OH
(a) Br
(c)
OCH2CH2Br
OH + BrCH2CH2Br
heat
(b)
Br + BrCH2CH2OH
(d)
Br + BrCH2CH2Br
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78. What is the product obtained by heating the following allylic ether of phenol ?
OCH2CH = CHC6H5
OH C|6H5
CHCH = CH2
OH
CH2CH = CHC6H5
(a)
(b)
OC6H5
CH2CH = CH2
(c)
C2H5
|
CHCH = CH2
(d) HO
79. When you ingest aspirin, it passes through your stomach, which has an acidic pH, before
traveling through the basic environment of your intestine. Provide the structure form as it
exists in the intestine.
O
O
OH
O – C – CH 3
(a)
CO2H
(b)
O-
O – C – CH3
CO2CH3
CO2
(c)
O
C – OH
(d)
80. Which of the following sets of reagents, used in the order shown, would be enable for the
preparation of p-chlorophenol from p-chloronitrobenzene ?
(a) 1. Fe, HCl ; 2. NaOH ; 3. NaNO 2 , H 2 SO 4 ; 4. H 3 PO 2
(b) 1. Fe, HCl ; 2. NaOH ; 3. NaNO 2 , H 2 SO 4 ; 4. H 2 O, heat
(c) 1. Fe, HCl ; 2. NaOH ; 3. NaNO 2 , H 2 SO 4 ; 4. ethanol
(d) 1. NaOH, heat ; 2. HCl
81. Which one of the following compounds undergoes bromination of its aromatic ring
(electrophilic aromatic substitution) at the fastest rate ?
(a)
(b)
OH
(c)
(d)
O
||
CH -C - Cl
NH
NH
N
H
O
Anhy. AlCl
D
3
3
¾ ¾¾¾
¾® ( P ) ¾ ¾¾¾¾
® (Q ). Product (Q) in this reaction is :
82.
O
O – Me
(a)
OCOMe
(b)
OMe
C – Me
(c)
(d)
OH
OH
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533
NO2
CH O –
3
¾ ¾¾¾
¾® ( P ) ; The product (P) will be :
83.
CH 3OH, D
Cl
(major)
Cl
NO2
(a)
(b)
(c)
Cl
OCH3
Cl
(d)
Cl
OCH3
CH2 – N – CH 2
|
CH2
OCH3
(A) ; Product (A) is :
HCl, 90°C
(a) Ph - CH 2 - N - CH 2 - Ph
OCH3
Cl
NaNO2,
84.
NO2
OCH3
NO2
(b) Ph - CH 2 - N - N == O
|
|
N=O
Ph
CH2 – Ph
(d) Ph – N = O
CH2 – Ph
N
||
(c) Ph – CH2 – N
|
N=O
NH2
N
|
+ NaNO2 + HCl
85.
N
|
H
NH2
This reaction is example of :
(a) Intermolecular C – N coupling
(b) Intramolecular C – N coupling
(c) Intermolecular N – N coupling
(d) Intramolecular N – N coupling
86. The total number of isomeric trimethylbenzene is :
(a) 2
(b) 3
(c) 4
(d) 6
87. Caliene, C 7 H 6 , is expected to be a fairly polar aromatic molecule. Which of the following
resonance forms contributes to the greatest extent towards the real structure (resonance
hybrid) of the molecule ?
+
(a)
(b)
–1
:–
(c)
(d)
Å
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534
88. Which of the following molecules is expected to have the greatest resonance stabilization ?
(a)
(b)
(c)
(d)
89. In the reaction given below, the major product formed is :
O
Br2(1 mole)
N
Fe
O
Br
O
N
(a)
Product.
N
(b)
Br
O
O
N
(c)
Br
N
(d)
Br
90. p-aminophenol reacts with one equivalent of acetyl chloride in the presence of pyridine to
give mainly :
O
OH
OH
OH
OCOCH3
C – CH3
(a)
(b)
(c)
NH2
NH2
NH2
(d)
C – CH3
NHCOCH3
O
91. Which of the following reactions can be used to prepare acetophenone ?
1. AlCl 3
heat
(a) C 6 H 6 + CH 3 COCl ¾ ¾¾¾
(b (C 6 H 5 COO) 2 Ca + (CH 3 COO) 2 Ca ¾ ¾
®
¾®
2. H 2O
1. CH 3 MgI
(c) C 6 H 6 CN ¾ ¾¾¾
¾®
(d) All of these
2. H 3O+
92. Consider the following sequence of reactions.
H PO
1.O 2, heat
3
4
C 6 H 6 + CH 3 CH = CH 2 ¾ ¾¾
¾
® A ¾ ¾¾¾¾
¾® B + C
+
heat
2. H 3O , heat
The products (B) and (C) are :
(a) benzaldehyde and acetaldehyde
(b) benzoic acid and acetic acid
(c) phenol and propionaldehyde
(d) phenol and acetone
93. An organic compound having the molecular formula C 8 H 10 O on being heated with I 2 and
dilute NaOH gives a yellow precipitate. The expected compound is :
(a) C 6 H 5 CH 2 CH 2 OH
(b) CH3
CH2OH
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535
(c) H3C
(d)
OH
CHOHCH3
CH3
94. The product (B) of the reaction sequence is :
Mg. Et O
1. CH CHO
2
3
CH2Br ¾ ¾¾¾
® A ¾ ¾¾¾
¾® B.
Cl
2. H 3O +
OH
|
(a) CH3CH
(b) Cl
CH2Br
(c) CH2CH
|
OH
OH
|
CH2CHCH3
(d) CH2=CH
CH2CHCH3
|
OH
CH2Br
95. Consider the following sequence of reactions.
OsO 4
1. HIO 4
NaHSO 3
2. NaOH, heat
¾ ¾¾¾® A ¾ ¾¾¾¾¾
¾® B. The final product (B) is :
CH3
CH2CHO
COOH
(a)
(b)
COOH
(c)
(d)
COCH3
COCH3
COOH
O
96. For the reaction, the product expected is :
O
MeMgBr (2 mole)
O ¾1.
¾¾¾¾¾¾
¾® product,
+
2. H 3O
O
Me
O
OH
(a)
O
(b)
O
Me OH
Me OH
OH
O
(c)
O
C
CH3
CH3
C
OH
(d)
Me Me
O
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536
97. Hydrogenation of naphthalene ( P ) with excess hydrogen gas stops cleanly at 1, 2, 3,
4-tetrahydronaphthalene (Q). What conclusion can be drawn from this experiment ?
excess H2
Pd — C (cat.)
(Q)
(P)
(a) the hydrogenation of P is exothermic
(b) one aromatic ring of P is more reactive than the aromatic ring of Q
(c) one aromatic ring of P is less reactive than the other ring of Q
(d) reduction of the first C = C of P is faster than reduction of the second or third C = C
98. Suggest the best reaction conditions for the synthesis shown below.
NO2
Br
(a) (1) HNO 3 , H 2 SO 2 ; then (2) Br 2
(b) (1) Br 2 ; then (2) HNO 3 , H 2 SO 2
(c) (1) CH 3 Br, AlBr 3 ; then (2) HNO 3 , H 2 SO 3
(d) HNO 3 , H 2 SO 2 , then (2) Br 2 , FeBr 3
Cl
99.
In the above compound Cl will liberated easily in the form of :
(a) Cl Å
(b) Cl (c) Cl ·
100. Consider the following sequence of reactions:
(d) Cl 2+
1. PCl 5
1. P4O10 . heat
PhCO 2 H ¾ ¾¾¾
® A ¾ ¾¾¾¾
¾® B. The final product (B) is :
2. NH 3
2. H 2 Ni
(a) benzonitrile
101.
(b) benzylamine
(c) aniline
(d) benzamide
The major product of the acetylation of salicylic acid with Ac 2 O H + followed by heating
with anhydrous AlCl 3 is :
COOH
COOH
OH
OH
(a)
O
(b) O
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537
COOH
O
OH
COOH
OH
(c)
(d)
O
102.
Which one of the following statements is True:
1
(a)
(b)
(c)
(d)
103.
PhLi adds to both compounds with equal ease
PhLi does not add to either of the compounds
PhLi reacts readily with 1 but does not add to 2
PhLi reacts readily with 2 but does not add to 1
The major product expected from the mono-bromination of phenyl benzoate is :
Br
Br
(a)
COO
(c) Br
104.
COO
106.
(b)
COO
(d)
COO
Br
The Birch reduction of benzoic acid gives :
(a)
105.
2
COOH (b)
COOH (c)
COOH (d)
COOH
The decreasing order of reactivity of meta-nitrobromobenzene (I), 2,4,6-trinitrobromobenzene (II), para-nitrobromobenzene (III), and 2,4-dinitrobromobenzene (IV) towards
HO - ions is :
(a) I > II > III > IV (b) II > IV > III > I (c) IV > II > III > I (d) II > IV > I > III
Which of the following tetracarboxylic acid form di-anhydride :
COOH
COOH
COOH
COOH
(a)
COOH
(b)
COOH
COOH
(c) neither (a) nor (b)
COOH
(d) both (a) and (b)
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538
CO2H
OH
2I- Cl
107.
¾ ¾¾® (A); unknown (A) is :
O
CO2H
C—I
OH
I
(a)
(b)
H+ D
P
(major)
I
OH
Cl
Ph – NH 2 + Ph 3 COH ¾ ¾¾®
NH2
CO2H
(c)
Cl
108.
CO2H
OH
(d)
I
I
I
(not a N-derivative), Product (P) is :
NH2
NH2
CPh3
CPh3
(a)
(b)
(c)
(d)
CPh3
109.
Deduce structure of (A).
CPh3
Br
2
4
(A) C 8 H 10 ¾ KMnO
¾¾¾
®( B ) C 8 H 6 O 4 ¾ ¾
¾
® C 8 H 5 BrO 4 (C ) (one-product only) :
Fe
(a)
(b)
(c)
(d)
110.
The deamination of Ph 2 C(OH)CH 2 NH 2 with NaNO 2 - HCl gives a product ( P ), which on
oxidation gives benzoic acid only. Identify the product (P).
O
||
(a) Ph - CH 2 - CH 2 - Ph
(b) Ph - C - CH 2 - Ph
O O
|| ||
(d) Ph - CH 2 - NH - Ph
(c) Ph - C - C - Ph
111.
2
2
Ph - CO 2 H ¾ ¾¾
¾
® A ¾ ¾¾
¾® B ¾ ¾
¾® Ph - CHO, unknown reagent (C) is :
SOCl
(a) LiAlH 4
(c) LiAlH(t -BuO) 3
Me NH
(C )
(b) NaBH 4
(d) PCC CH 2 Cl 2
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539
CH2CH3
O
CH2CH3
CH3 — C — Cl
112.
AlCl3
NH2 — NH2, NaOH
(A)
triethylene glycol. heat
(80%)
(B)
(73%)
CH2CH3
Product ( B ) is :
(a)
113.
(b)
(c)
(d)
O
||
KMnO 4 , D
AlCl 3
® ( A) ¾ ¾ ¾¾
¾®( B ) ; Compound (B) is :
C 6 H 5 (CH 2 ) 5 C - Cl ¾ ¾¾
CS 2
H 3Or
C12H14O
CO2H
(a)
(b)
C — (CH2)4 — CO2H
O
O
CO2H
C
(c)
O
(d)
C
CO2H
O
R
R
NO2
HNO3
114.
R
+
H2SO4
(ortho)
NO2
In the above reaction o/p ratio will be highest when :
(a) R = - CH 3
(c) R = - CHMe 2
(b) R = - CH 2 - CH 3
(d) R = - CMe 3
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540
CO2H
Base
n -PrCl
HNO
SOCl
(1) Et NH
3
2
2
¾ ¾¾
¾
® (1) ¾ ¾¾
¾® (2) ¾ ¾¾
¾
® (3) ¾ ¾¾¾
¾®(4)
115.
(2) H 2 Pd
HO
product (4) in the above reaction is :
O
NO2
C — N — Et
Et
(a)
O
NH2
C — N — Et
(b)
O
Et
O
NH2
O
O
NO2
C — NEt2
C — NH — Et
(c)
(d)
O
O
Cl
Br
Cl
116.
(A); Product (A) of the reaction is :
AlCl3
Br
H
Br
Br
(a)
(b)
(c)
(d)
H
117.
Ph - CHO + 2
H SO
2
4
¾ ¾¾
¾
® major product of this reaction is :
OH
|
(b) Ph -C - Ph
|
Ph
(a) Ph 3 CH
(c)
Ph
NH2
Br
118.
(a)
(d) Ph 2 CH 2
Cl
Ph
(A); Product (A) of this reaction is :
(b)
N—H
(c)
N
|
H
(d)
Cl
N
|
H
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541
NO2
HNO + H SO
3
2
4
¾ ¾¾¾¾
¾
® (X); Compound (X) is :
119.
five days
to complete
NO2
(a) 1,2,4-Trinitrobenzene
(c) 1,2,3 -Trinitrobenzene
(i) HCl
(ii) SOCl 2
120.
(b) 1,3,5-Trinitrobenzene
(d) Tri-nitro toluene (TNT)
Ph - H
AlCl 3
KOH MeOH
¾ ¾¾¾
¾®( A) ¾ ¾¾®( B ) ¾ ¾¾¾¾® (C); Compound (C) is :
O
O
O
O
||
(b) Ph - CH = CH - C - CH 3
(a) Ph — CH2 — C —
O
O
||
(d) Ph - C - CH = CH - CH 3
(c) Ph — C —
O
C 6H 6
(i) PCl 5
NH - NH
2
2
¾
®(C ); Compound (C) is :
¾¾®( A) ¾ ¾¾¾¾¾¾®( B ) ¾ ¾¾¾
O ¾ AlCl
(ii) H Pd - BaSO
121.
3
O
2
4
H
Ph
C == N
C == N
(a)
(b)
CH == N
CH == N
CH == CH — Ph
C == N
(c)
(d)
CH == N
Ph
OH
(i) aq NaHCO 3 boil
¾ ¾¾¾¾¾¾
¾® ( A) , Product (A) in this reaction is :
+
122.
H 3O
OH
(major)
OH
OH
(a)
(b)
OH
OH
CHO
OH
CO2H
(c)
(d) No reaction
OH
OH
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542
iv
123.
NO2
I
, Identify position where attack of (ArO - ) is favourable.
iii
i
ii
(a) i
(b) ii
(c) iii
(d) iv
S — S
Cl
124.
2
¾¾
¾
®( A ), Product (A) of this reaction is :
NO2 NO2
SH
S — Cl
SH
(a)
NO2
(b)
(c)
(d)
NO2
NO2
NO2
NO2
O
C — Me
125.
HNO 3
Zn(Hg)
H 2SO 4
HCl
¾ ¾¾
¾® (A) ¾ ¾¾
¾® (B), Product (B) of this reaction is :
CH2 — Me
O
CH2 — Me
C — Me
CH2 — Me
NO2
(a)
(b)
(c)
NO2
(d)
NH2
NO2
Me
H O+
AlCl
3
3
+HN = CH - Cl ¾ ¾¾
®( A) ¾ ¾¾
®( B ), Product (B) of this reaction is :
126.
CH3
Me
(a)
(b)
(c) No-reaction
CHO
O
C — Me
CHO
CH2CO2H
127.
(d)
EtOH
(i) NaH
(ii) MeI
(i) NaOH
(i) SOCl
2
® ; Product
¾ ¾¾® ¾ ¾¾¾® ¾ ¾¾¾
® ¾ ¾¾¾
+
H+
(ii) H
(ii) AlCl 3
End product of the above reaction is :
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543
O
Me
(a)
(b)
O
O
(c)
(d)
Å
128.
O
CH 3 -Cl (2 mole)
–
Ph -N 2 Cl
Ph - NH 2 ¾ ¾¾¾¾¾
¾®(A) ¾ ¾¾¾®
(B)
(major)
Butter yellow
Product of the above reaction is :
Me
Me
N
Me — N — Me
N == N — Ph
(a)
(b)
Me
Me — N — Me
N == N — Ph
Me — N — N == N — Ph
(c)
129.
(d)
N == N — Ph
p-Toluedine reacts with benzene diazonium chloride to form compound, which on boiling
with aq. H 2SO 4 give ......... products :
(a) 3
(b) 2
(c) 4
(d) 5
NO2
Br2
(i) NaNO +HCl
H 2O
(ii) H 3 PO 2
aq NH
3
2
¾ ¾¾¾
®( A) ¾ ¾¾® ( B ) ¾ ¾¾¾¾¾
® (C )
130.
Cl
Product (C) of the above reaction is :
NO2
NO2
NO2
NO2
Br
(a)
(b)
Br
(c)
Br
Br
Br
(d)
Br
Br
Br
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544
Fe+2
131.
¾ ¾¾®
H 2O 2
(Fenton's reagent)
Br
H 2O
2
( A) ¾ ¾
¾
®
( B)
; Major product (B) of this reaction is :
( ºº 100%)
OH
OH
CH
OH
Br
Br
(a)
(b)
(c)
Br
(d)
Br
Br
Br
Br
NO2
–
HO
¾ ¾¾® (A) ; Product of the given reaction is :
132.
Br
Br
OH
NO2
NO2
(a)
(b)
OH
Br
Br
Br
NO2
NO2
HO
(c)
(d)
HO
Br
NH2
(CH CO) O
HNO
H 2SO 4
H+
3
2
3
¾ ¾¾¾¾
® ( A) ¾ ¾¾
¾
® ( B ) ¾ ¾¾® (C ), Product (C) of this reaction is :
133.
NH2
H 2O
NO2
NH2
(a)
(b)
NO2
(c)
NO2
(d)
NO2
NO2
NO2
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545
NO2
Br (2 mole)
Fe
2
¾ ¾¾¾¾
® ( A) (major) ; Product (A) will be :
134.
NO2
NO2
NO2
NO2
Br
Br
(a)
(b)
(c)
Br
Br
Br
(d)
Br
Br
Br
(i) HNO 3
KMnO
SOCl
D
2
4
¾ ¾¾¾¾® ( A) ¾ ¾¾¾
¾® ( B ) ¾ ¾¾
¾
® (C ); Product (C) of this reaction is :
135.
(ii) H 2SO 4
(Di- nitro
product)
O
COCl
C — Cl
(a)
NO2
NO2
NO2
(b)
(c)
(d)
NO2
NO2
NO2
NO2
NO2
Cl
CH — NH—CH
Fe
3
3
¾ ¾¾¾¾¾
¾
® ( A) ¾ ¾
¾® ( B ) ; Product (B) of this reaction is :
136.
HCl
NO2
CH3
N
CH3
CH3
(a)
N
CH3
(b)
NH2
NH2
CH3
N
CH3
NH2
(c)
(d) None of these
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546
OH
NH2
137.
(A)
(i)SOCl 2
Br2+ KOH
¾ ¾¾¾
® ( B ) ¾ ¾¾¾
¾®
(ii) NH 3
Which of the following compound on hydrolysis gives reactant (A) :
O
O
(a)
(b)
C—O
NO2
C—O
HO
HO
O
O
(c) NO2
NO2
(d)
C—O
C—O
NO2
HNO
OH
H SO
3
2
4
¾ ¾¾¾¾
¾
® (A);
138.
MeO
Product (A) of the above reaction is :
NO2
NO2
NO2
(a)
(b)
MeO
MeO
NO2
(c)
(d)
MeO
MeO
Me
NO2
O
139.
Br2
¾¾
¾® ; Product of the reaction is :
N
|
H
CS 2
Br
O
(a)
O
(b)
NH
NH
H2
—
CH2 — Br
Br
C
O
(c)
O
(d)
NH
NH
Br
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OH
O
O
H2
140.
Pd
O
(A)
( B)
; Product (B) of this reaction is :
(Paracetamol)
NO2
O
O — C — CH3
OH
OH
O
NH2
C — CH3
(a)
(b)
(c)
NH2
HN
NH2
OH
O
O
AlCl 3
Zn(Hg)
H 3 PO 4
O ¾ ¾¾¾¾¾
® ( A) ¾ ¾¾
¾® ( B ) ¾ ¾¾
¾® (C ) ;
+
141.
(d)
2.2 equivalents
HCl
O
(succinic
anhydride)
Product (C) of the above reaction is :
O
OH
O
(a)
OH
(b)
(c)
(d)
O
+
142.
C
AlCl
O
3
¾ ¾¾
® Product;
82% yield
H
Product of the above Friedel-Craft reaction is :
O
(a)
CO2H
C
(b)
CO2H
(c)
(d)
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548
143.
Which of the following 2-halo nitrobenzene is most reactive towards nucleophilic aromatic
substitution ?
F
I
Cl
Br
NO2
(a)
144.
NO2
(b)
NO2
NO2
(c)
(d)
Choose the best method to prepare given compound :
CH3
CH3
CH3
NO2
(a)
(1) HNO +H SO
3
2
4
¾ ¾¾¾¾¾¾
®
(1) Me CCl AlCl
3
3
¾ ¾¾¾¾¾
¾
®
(b)
(2) Me3CCl AlCl 3
(2) HNO 3 H 2SO 4
CH 3
|
(1) HNO 3 H 2SO 4
(1) CH —CH— CH —Cl/AlCl
3
2
3
¾ ¾¾¾¾¾¾¾¾¾¾
¾
® (d)
(c)
¾ ¾¾¾¾¾¾¾¾¾®
(2)CH 3 -CH - CH 2 -Cl AlCl 3
(2) HNO 3 H 2SO 4
|
CH 3
CH3
HNO 3
145.
¾ ¾¾
¾®
H 2SO 4
H2
EtOH
KMnO
4
¾ ¾¾® ( B ) ¾ ¾¾¾
® (C ) ¾ ¾¾®
( A)
Pd,C
(Para isomer)
H+
( D)
Benzocaine
Benzocaine has been used as a component of appetite suppressants, burn and sunburn
remedies. Benzocaine is :
O
CO2Et
CO2Et
C
OEt
NH
C
(a)
(b)
(c)
NH2
(d)
NH2
O — CH3
HBr
D
146.
O
NH2
¾ ¾¾® ( A) ; Product (A) of this reaction is :
OH
Br
(a)
86%
(b)
OH
OH
OCH3
(c)
Br
OCH2 — Br
(d)
OH
CH
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549
OCH3
OCH3
147.
HI(excess)
¾ ¾¾¾¾® Product.
D
OCH3
Predict major product of the above reaction is :
OH
I
OH
(a)
OH
CH3
O—I
I
(b)
(c)
OH
(d)
OH
I
OH
HNO
HNO 3
2
¾ ¾¾
¾
® (A) (Major) ; Product (A) is :
148.
OH
OH
OH
NO2
(a)
(b)
(c)
(d)
NO2
149.
NO
Arrange in their decreasing order of rate in SNAr.
Cl
Cl
Cl
Cl
NO2
Cl
NO2
NO2
NO2
NO2
NO2
(i)
150.
(iii)
(ii)
NO2
(iv)
(v)
(a) i > ii > iv > iii > v
(b) ii > i > iii > v > iv
(c) v > iii > i > ii > iv
(d) v > iii > ii > i > iv
Which one of the following compounds undergoes bromination of its aromatic ring
(electrophilic aromatic substitution) at the fastest rate ?
(a)
(b)
N
H
(c)
NH
(d)
NH
O
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151.
What is the product of the following reaction ?
CH3
OCH3 +
C == CH2
H2SO4
OCH3
CH3
152.
(a)
CHCH2
(c)
CH3
|
CHCH2
OCH3 (b) (CH3)2CH
OCH3
(d) (CH3)2CH
OCH3
Which sequence represents the best synthesis of 4-isopropylbenzonitrile ?
(CH3)2CH
C ºº N
4-Isopropylbenzonitrile
(a) 1. Benzene + (CH 3 ) 2 CHCl, AlCl 3 ;
(b) 1. Benzene + (CH 3 ) 2 CHCl, AlCl 3 ;
4. NaOH
(c) 1. Benzene +(CH 3 ) 2 CHCl, AlCl 3 ;
4. NaNO 2 HCl
(d) 1. Benzene + HNO 3 ,H 2 SO 4 ;
4. NaNO 2 ,HCl,H 2 O;
CH3
2.
2.
5.
2.
5.
2.
5.
3.
Br 2 ,FeBr 3 ;
HNO 3 ,H 2 SO 4 ; 3.
NaNO 2 , HCl, H 2 O
HNO 3 , H 2 SO 4 ; 3.
KCN
(CH 3 ) 2 CHCl, AlCl 3 ;
CuCN
KCN
Fe, HCl,;
Fe, HCl ;
3. Fe, HCl;
Br
1. Mg Ether
153.
¾ ¾¾¾¾¾
¾® A, Product A is :
+
2. H 3O
3. KMnO 4 OH 4. H +
OH
COOH
OH
(a)
CH3
(b)
COOH
(c)
(d)
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551
1. Air, V 2O 5, D
154.
¾ ¾¾¾
¾® A, Product A is :
2. NH 3 , D
3. KOBr, D
CO
COOH
NH
(a)
(b)
CO
NH2
O
C
COOH
(c)
(d)
NH
CONH2
155.
What is correct order of rate of nitration of the following compounds ?
+
C 6 H 5 CH 3
A
C 6H 6
B
C 6D 6
C
C 6T6
D
C 6 H 5 Br 3
E
(a) G > A > B > C > D > E > F
(c) G > A > B = C = D > E > F
F
C 6 H 5 NMe 2
G
(b) G > B > C > D > A > F
(d) G > A > B > C = D > E > F
COCl AlCl
Na— Hg, HCl
3
+ |
¾ ¾¾
®[ X ] ¾ ¾¾¾¾
¾®[Y ] ; Product Y is :
excess
COCl
156.
157.
C 6H 5 N R 3
(a)
(b)
(c)
(d)
Compound A (C 7 H 8 O) is insoluble in water, dilute HCl & aqueous NaHCO 3 , but it dissolves
in dilute NaOH. When A is treated with Br 2 water it is converted into a compound C 7 H 5 OBr 3
rapidly. The structure of A is :
OH
OCH3
OH
OH
CH3
(a)
(b)
(c)
(d)
CH3
CH3
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552
158.
Give the product of the following reaction sequence :
1. HNO 3 H 2SO 4
2. H 2 Pd C
¾ ¾¾¾¾¾® Product
3. NaNO 2 HCl
4. CuCN
5. MeMgBr
6. H 3O+
O
CO2H
(a)
159.
CO2H
(b)
OH
(c)
(d)
Give the product of the following reaction sequence:
1. HNO 3 H 2SO 4
2. Br2 FeBr3
¾ ¾¾¾¾¾® Product
3. H 2 Pd C
4. Cl 2 FeBr3
5. NaNO 2 HCl
6. KI
Cl
I
I
Br
(a)
Br
Cl
Cl
(b)
(c)
I
(d)
CH2
CH2
The decreasing order of reactivity of m-nitrobromobenzene (I), 2, 4, 6- trinitrobromo-benzene
(II), p-nitrobromobenzene (III), and 2,4-dinitrobromobenzene (IV), towards OH - ions is :
(a) I > II > III > IV
(c) IV > II > III > I
162.
(d)
Which represents an intermediate formed in the reaction of toluene and chlorine at elevated
temperature in sunlight ?
H
H
(a)
(b)
CH3
CH3
Cl
Cl
(c)
161.
Cl
Br
I
160.
Br
(b) II > IV > III > I
(d) II > IV > I > III
Which one of the following compounds is most reactive for ArS N 2 reaction ?
Cl
Cl
Cl
Cl
(a)
(b)
NO2
NO2
NO2
(c)
(d)
NO2
NO2
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553
163.
Which one amongst the following carbocations is most stable ?
Å
(a) C 6 H 5 — C H — C 6 H 5
(b)
C
Å
(c) CH 3 — C — CH 3
|
CH 3
164.
(d)
Cyclopentadiene is much more acidic than cyclopentane. The reason is that :
(a) cyclopentadiene has conjugated double bonds
(b) cyclopentadiene has both sp 2 and sp 3 hybridized carbon atoms
(c) cyclopentadiene is a strain-free cyclic system
(d) cyclopentadienide ion, the conjugate base of cyclopentadiene, is an aromatic species and
hence has higher stability
COCH3
COCH3
COCH3
COCH3
165.
H3C
CH3O
(I)
O2N
(II)
Me2N
(III)
(IV)
Friedel-Crafts acylation reaction can be used to obtain the compounds
(a) II, III and IV
(c) I and II
166.
(b) I, III and IV
(d) II and III
The major product of the reaction is :
Br2
FeBr3
(a)
Br
Product
(b)
Br
(c)
(d)
Br
Br
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554
167.
The decreasing order of reactivity of given compound towards nucleophilic substitution with
aqueous NaOH is :
Br
Br
Br
Br
O2N
NO2
NO2
NO2
NO2
NO2
(I)
(II)
(a) I > II > III > IV
(c) IV > II > III > I
168.
NO2
(III)
(IV)
(b) II > IV > III > I
(d) II > IV > I > III
Identify the end product (B) of the following sequence of reactions.
OH
conc. H SO
Br H O
100°C
(excess)
2
4
2
2
¾ ¾¾¾¾
¾
® A ¾ ¾¾¾
®B
OH
OH
Br
Br
Br
(a)
OH
OH
Br
(b)
Br
SO3H
(c)
Br
(d)
Br
SO3H
169.
Br
Br
Consider the following sequence of reactions :
COOH
SOCl
1. AlCl
Zn— Hg
2. H 3O +
conc. HCl, heat
2
3
¾ ¾¾
¾
® A ¾ ¾¾¾
® B ¾ ¾¾¾¾¾® C
CH2C6H5
The end product (C) is :
O
(a)
O
(b)
C6H5
C6H5
O
(c)
O
(d)
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170.
For the diazonium ions the order of reactivity towards diazo-coupling with phenol in the
presence of dilute NaOH is :
N2+ O2N
Me2N
(I)
N2+ CH3O
(II)
(III)
(a) I < IV < II < III
(c) III < I < II < IV
171.
N2+ CH3
N2+
(IV)
(b) I < III < IV < II
(d) III < I < IV < II
Major product obtained in given reaction is :
+
H SO
2
4
¾ ¾¾
¾
®
(2 mole)
(a)
(b)
(c)
(d)
Å
H
¾¾
¾® ( B ) ; (A) & (B) are isomers. Product (B) is :
172.
(A)
or AlCl 3 (major)
Dewar's Benzene
(a)
(b)
(c)
(d)
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173.
The step shown below is a recent synthesis of corannulene.
¾ ¾¾® ( A) C 20 H 10
Pd C
( D)
Corannulene
Product (A) is :
(a)
(b)
(c)
(d)
a
174.
c
d
b
Identify the position where E.A.S. will take place :
(a) a
(b) b
(c) c
(d) all the position are identical
14
175.
CH2 — CO2H
(1) KMnO , HO - , D
4
¾ ¾¾¾¾¾¾
¾®
( 2) H 3O Å
The labelled carbon goes with :
14
14
(a) Ph — CO 2 H
176.
14
(b) CO 2
14
(c) Ph — CH 2 — CO 2 H
(d) CH 4
What is the expected order of reactivity of the following compounds in electrophilic
chlorination (Cl 2 + FeCl 3 ) ?
(more reactive > less reactive)
I
II
III
IV
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557
177.
(a) I > II > III > IV (b) IV > III > II > I (c) III > I > IV > II (d) II > III > I > IV
Which of the following is the major product from sulfonation of a-tetralone ?
O
H2SO4
heat
SO3H O
O
HO3S
(a)
(b)
O
O
(c)
(d)
HO3S
178.
SO3H
Which of the following procedures would be best for the preparation of phenyl benzyl ether ?
C 6 H 5 OCH 2 C 6 H 5
179.
(a) C 6 H 5 Cl + C 6 H 5 CH 2 O ( -)Na ( + )
(b) C 6 H 5 O ( -)Na ( + ) + C 6 H 5 CH 2 Cl
(c) 2C 6 H 5 Cl + Na 2 O
(d) 2C 6 H 5 MgBr + CH 2 O
Which of the following procedures would be best for achieving the following reaction ?
CH3
CH2–Cºº CH3–CH3
?
Br
Br
(a) (i) KOH and heat (ii) CH 3 C ºº C — Br
(b) (i) KMnO 4 and heat
(ii) CH 3 C ºº C ( -)Na ( + ) (iii) excess H 2 O
(c) (i) NBS in CCl 4 and heat (ii) CH 3 C ºº C ( -)Na ( + )
(d) (i) Mg in ether
180.
(ii) CH 3 C ºº CBr
(iii) excess H 3 PO 4
Which of the following procedures would be best for achieving the following reaction ?
CH3
Cl
(a)
(b)
(c)
(d)
?
O2N
Cl
CO2H
Br
(i) Br 2 + FeBr 3
(ii) KMnO 4 and heat (iii) HNO 3 and H 2 SO 4
(i) KMnO 4 and heat (ii) Br 2 + FeBr 3
(iii) HNO 3 and H 2 SO 4
(i) NBS in CCl 4 and heat (ii) KMnO 4 and heat (iii) HNO 3 and H 2 SO 4
(i) NBS in CCl 4 and heat (ii) NaNO 2 and heat
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181.
Phenol reacts with acetone in the presence of conc. sulphuric acid to form a C 15 H 16 O 2
product. Which of the following compounds is this product ?
O–C6H5
OH
(a)
(b) HO
O–C6H5
O
O
(c)
(d)
O
182.
C6H5
O
Heating benzene in a large excess of 80% D 2 SO 4 in D 2 O results in what product ?
(a) C 6 H 5 SO 3 D
183.
(b) C 6 H 5 OD
(c) C 6 H 5 D
(d) C 6 D 6
A solution of cyclohexene in benzene is stirred at 0°C while concentrated sulphuric acid is
added. After washing away the acid and removing the excess benzene, what product is
isolated?
(a) cyclohexylbenzene
(c) trans-1,2-diphenylcyclohexane
184.
C6H5
(b) 1-cyclohexylcyclohexene
(d) 1,1-diphenylcyclohexane
Indentify the reagents S and m in the scheme below in which R is converted to the nitrite V via
the benzylic halide T.
CH2 — Br
(S)
CH2 —CN
(m )
(R) ¾ ¾
¾®
¾¾
¾®
O
O
R, S and m respectively are :
R
(a)
S
Cl
m
H—C—
(AlCl 3 )
O
CH2Br
Cl —C —
(b)
O
O
(d)
(AlCl 3 )
— C —Cl
HCN
CH2Br
Cl —C —
(c)
HCN
(AlCl 3 )
KCN
CH2Br
CH2Br
(AlCl 3 )
KCN
O
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559
185.
Two aromatic compounds P and Q give product R.
Reagent(s)
P + Q ¾ ¾¾¾¾®
Reactant P, Q and reagent used in above reaction are :
P
Q
CH3
— C — Cl
(a)
Reagent
AlCl 3
O
Cl
—C—H
(b)
CH3
AlCl 3
O
CH3
(c)
AlCl 3
C ==O
Cl
O
(d)
186.
CH3
Cl — C
ZnCl 2
Which of the following C 6 H 6 compounds has a single set of structurally equivalent hydrogen
atoms ?
H — C ºº C — C H 2 — C H 2 — C ºº C — H
(a) I and II
187.
(b) I and IV
(b)
(c)
(d) I, II and III
(d)
N
N
A C 8 H 10 hydrocarbon is nitrated by HNO 3 and sulphuric acid. Two, and only two,
C 8 H 9 NO 2 isomers are obtained. Which of the following fits this evidence ?
(a) ethyl benzene
189.
(c) I and V
V
Which of the following compounds would not be considered aromatic in its behaviour?
(a)
188.
IV
III
II
I
(b) ortho-xylene
(c) meta-xylene
(d) para-xylene
Which of the following benzene ring substituents is deactivating but ortho-para directing ?
(a) —N == O
(b) — OCH 3
(c) — COCH 3
(d) — NO 2
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190.
Which of the following compounds forms ortho- benzenedicarboxylic acid when oxidized by
hot aqueous potassium permanganate ?
(a)
191.
192.
(b)
(c)
(d)
Which of the following organic chlorides will not give a Friedel-Craft alkylation product
when heated with benzene and AlCl 3 ?
(a) (CH 3 ) 3 CCl
(b) CH 2 == CHCH 2 Cl (c) CH 3 CH 2 Cl
Which of the following is aromatic ?
..
Å
Q
(d) CH 2 == CHCl
(a)
(d)
(b)
(c)
(carbene)
(carbene)
193.
..
Which of the following substance will increase the acidity of phenol ?
(a) Dil. H 2 SO 4
(b) Dil. HCl
(c) Conc. H 2 SO 4
(d) Conc. CH 3 COOH
194.
+ PhMgBr ¾® E + F
N
|
H
Pyrrole
E + MeCl ¾® G + H
F + MeCl ¾® no reaction without a catalyst
N
H
1
N
N
MgBr
Ph
H
4
3
2
Ph
Me
N
N
H
H
5
Ph
Me
N
H
7
6
The structure of products E – H, respectively are
(a) 3, 2, 6, 7
(b) 4, 5, 6, 1
(c) 3, 4, 5, 2
O
195.
(d) 3, 2, 4, 5
H+
¾¾
¾® (A); Product A is :
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561
O
OH
(a)
(b)
O
(c)
(d) none of these
O
H+
196.
R
R
Identify the product of the above rearrangement reaction.
O
O
O
(a)
(b)
R
197.
R
OH
(c)
R
R
(d)
R
R
R
R
Product obtained in the following transformation is :
O
PPA
PPA = polyphosphoric acid
¾ ¾¾®
Ph
O
Ph
(a)
(b)
Ph
O
O
(c)
(d)
Ph
198.
The compound X in the reaction.
+ ICl
anhydrous AlCl3
X
I
Cl
I
Cl
(a)
(b)
(c)
(d)
Cl
I
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OH
OH
Br
Br
+ 3Br2
199.
+3HBr
Br
(a) Nucleophilic addition
(c) Electrophilic addition
(e) Free radical substitution
CH2Br
CH3
+Br2
200.
(b) Nucleophilic substitution
(d) Electrophilic substitution
+HBr
(a) Nucleophilic addition
(c) Electrophilic addition
(e) Free radical substitution
(P)
hv
(b) Nucleophilic substitution
(d) Electrophilic substitution
/
Cl 2
201.
Cl
2 /A
l
Cl
3
(Q)
Identify major product of both respectively.
CH2—Cl
Cl
(a)
(b)
Cl
Cl
Cl
Cl
(c)
(d)
Cl
Cl
OH
202.
Cl
OH
pH == 10-11
+ Ph — N 2+ Cl - ¾ ¾¾¾¾®
N==N—Ph
Characteristics of above reaction is :
(a) C — N coupling reaction ; Carbocation is intermediate
(b) N — N coupling reaction ; Carbocation is intermediate
(c) C — N coupling reaction ; Carbanion is intermediate
(d) N — N coupling reaction ; Carbanion is intermediate
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203.
The compound formed on heating chlorobenzene with chloral in the presence of
concentrated sulphuric acid, is :
(a) Freon
204.
(b) DDT
(c) Gammexene
(d) Hexachloroethane
Predict the product of the following reaction.
O
1.
Cl
/AlCl3
2. Zn(Hg), HCl
3. Br2, FeBr3
O
O
Ac2O
(a)
(b)
Br
Br
O
(c)
205.
(d)
Br
Br
Predict the major product of the following reaction sequence.
Cl
AlCl
Br FeBr
1. Fe, HCl
NaOH
2
3
2
3
¾
® D ¾ ¾¾
¾® E
¾ ¾¾¾
¾
® A ¾2¾¾¾
® B C ¾ ¾¾¾
. NaOH
H SO , NaNO
2
(a)
(b)
(c)
Cl
(d)
Br
Cl
Br
O
Give the major product of the following reaction :
O
NHPh
O
CH Cl, AlCl
3
3
¾ ¾¾¾¾
¾
®
O
O
NHPh
(a)
2
Br
Cl
Br
Cl
206.
H PO
2
4
2
3
2
¾ ¾¾¾¾¾
® F ¾ ¾¾
¾
®G
H O
H O
NO2
NHPh
(b)
H3C
CH3
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564
NHCOPh
NHCOPh
(c)
(d)
H3C
CH3
CH3
Br
NaNO + HCl
Sn HCl
H PO
KMnO
2
2
3
2
4
¾¾
¾
® ( A) ¾ ¾¾¾® ( B ) ¾ ¾¾¾¾
¾® (C ) ¾ ¾¾
¾
® ( D) ¾ ¾¾
s¾® ( E )
Fe
207.
HO
NO2
Product ( E ) is :
CO2H
CO2H
CO2H
CO2H
Br
(a)
(b)
(c)
(d)
Br
CO2H
Br
F
O
NO2
NH2–NH2
208.
A
B ; Products;
H+, D
NO2
Incorrect statements regarding above reaction is
209.
210.
(a) Product A is 2, 4-DNP
(b) A to B dehydration reaction
(c) A to B, geometrical isomersm will obtained as a product
(d) B is known as oxime
(i) chlorobenzene is mono-nitrated to M
(ii) nitrobenezene is mono-chlorinated to N
(iii) anisole is mono-nitrated to P
(iv) 2-nitrochlorobenzene is mono-nitrated to Q.
Out of M, N, P and Q the compound that undergoes reaction with aq. NaOH fastest is
(a) M
(b) N
(c) P
(d) Q
For the transformation the reagent used is
Br
Br
Å
N2 Cl2
(a) LiAIH 4
(b) H 3 PO 2
(c) H 3 O +
(d) H 2 / Pt
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565
211.
The reaction
OH
OH
CHO
+
212.
is known as
(a) Perkin reaction
(b) Sandmeyer reaction
(c) Reimer-Tiemann reaction
(d) Cannizzaro reaction
A compound X formed after heating coke with lime react with water to give Y which on
passing over redhot iron at 873 produces Z. The compound Z is
(a)
213.
NaOH/Heat
CHCl3
H+
(b)
(c)
(d)
The reaction of 50% aq KOH on an equimolar mixture of 4-methylbenzaldehyde and
formaldehyde followed by acidification gives :
OH
OH
OH
+ HCOOH
(a)
(b)
H3C
H3C
CHO
COOH
+CH3OH
(c)
(d)
H3C
214.
OH
Which isomer of xylene can give three different monochloroderivatives ?
(a) o-xylene
(b) m-xylene
(c) p-xylene
(d) xylene cannot give a monochloro derivative
CH3
CH3
CH3
D D
D
215.
216.
217.
(I)
(II)
(III)
The rate of o-nitration of the above compounds, (I) toluene, (II) 2-D-toluene and (III) 2, 6D 2 -toluene is in the following order
(a) I > II > III
(b) II > I > III
(c) III > I > II
(d) The rate is the same for all the three compounds
Cyclooctatetraene is expected to have :
(a) a planar structure
(b) a tub-shaped structure
(c) open chain isomeric structure
(d) tatutomeric bicyclic structure
red hot
CH 3COCl
Ni/ H 2
Fe
AlCl 3
25°C
3HC ºº CH ¾¾¾® ( A) ¾¾¾¾® ( B ) ¾¾¾® C + D
Relation between C and D.
(a) ldentical
(b) enantiomer
(c) diastereomer (d) position
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566
ANSWERS — LEVEL 1
1.
(b)
2.
(d)
3.
(b)
4.
(c)
5.
(a)
6.
(b)
7.
(c)
8.
(b)
9.
(d)
10.
(d)
11.
(a)
12.
(a)
13.
(a)
14.
(a)
15.
(a)
16.
(b)
17.
(b)
18.
(a)
19.
(b)
20.
(b)
21.
(c)
22.
(c)
23.
(b)
24.
(b)
25.
(d)
26.
(c)
27.
(c)
28.
(b)
29.
(b)
30.
(b)
31.
(b)
32.
(a)
33.
(b)
34.
(d)
35.
(c)
36.
(c)
37.
(a)
38.
(c)
39.
(a)
40.
(b)
41.
(b)
(b)
42.
(c)
43.
(c)
44.
(b)
45.
(c)
46.
(b)
47.
(b)
48.
49.
(b)
50.
(b)
51.
(b)
52.
(a)
53.
(c)
54.
(c)
55.
(a)
56.
(a)
57.
(d)
58.
(b)
59.
(b)
60.
(b)
61.
(c)
62.
(b)
63.
(b)
64.
(b)
65.
(a)
66.
(a)
67.
(c)
68.
(b)
69.
(a)
70.
(d)
71.
(b)
72.
(a)
73.
(a)
74.
(c)
75.
(a)
76.
(d)
77.
(c)
78.
(b)
79.
(c)
80.
(b)
81.
(b)
82.
(c)
83.
(a)
84.
(c)
85.
(d)
86.
(b)
87.
(d)
88.
(b)
89.
(d)
90.
(d)
91.
(d)
92.
(d)
93.
(d)
94.
(b)
95.
(c)
96.
(d)
97.
(b)
98.
(d)
99.
(b)
100.
(b)
101.
(b)
102.
(c)
103.
(d)
104.
(a)
105.
(b)
106.
(d)
107.
(c)
108.
(c)
109.
(b)
110.
(b)
111.
(c)
112.
(b)
113.
(c)
114.
(a)
115.
(b)
116.
(b)
117.
(a)
118.
(b)
119.
(b)
120.
(c)
121.
(c)
(b)
122.
(b)
123.
(c)
124.
(b)
125.
(b)
126.
(b)
127.
(c)
128.
129.
(c)
130.
(b)
131.
(d)
132.
(b)
133.
(b)
134.
(a)
135.
(b)
136.
(a)
137.
(b)
138.
(c)
139.
(d)
140.
(b)
141.
(b)
142.
(c)
143.
(a)
144.
(b)
145.
(b)
146.
(c)
147.
(a)
148.
(c)
149.
(c)
150.
(b)
151.
(d)
152.
(c)
153.
(c)
154.
(b)
155.
(c)
156.
(c)
157.
(c)
158.
(b)
159.
(c)
160.
(c)
161.
(b)
162.
(c)
163.
(d)
164.
(d)
165.
(c)
166.
(c)
167.
(b)
168.
(d)
169.
(d)
170.
(b)
171.
(b)
172.
(a)
173.
(a)
174.
(b)
175.
(b)
176.
(d)
177.
(b)
178.
(b)
179.
(c)
180.
(a)
181.
(b)
182.
(d)
183.
(a)
184.
(c)
185.
(c)
186.
(b)
187.
(b)
188.
(b)
189.
(a)
190.
(b)
191.
(d)
192.
(b)
193.
(c)
194.
(a)
195.
(c)
196.
(b)
197.
(b)
198
(b)
199
(d)
200
(e)
201.
(c)
203.
(b)
204.
(c)
205.
(a)
206.
(c)
207.
(c)
208.
(d)
(a)
211.
(c)
212.
(a)
213.
(b)
214
(b)
215.
(d)
216.
(b)
(c)
202.
209.
(d)
210.
217.
(b)
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567
Level - 2
1.
Each of the six compounds shown at the bottom of the page has two aromatic (benzene)
rings. In each case the two rings are different and are labeled A & B. If an electrophilic
substitution, such as nitration or bromination, is carried out on each compound,
then identify which ring (A or B) will be preferentially attacked, and indicate the orientation
of the substitution (ortho/para, meta or all sites).
Compound Reactivity
1.
Substitution
A
ortho/para
B
meta
Compound Reactivity Substitution
2.
A
ortho/para
B
meta
all sites
3.
A
ortho/para
B
meta
all sites
4.
A
ortho/para
B
meta
all sites
5.
A
ortho/para
B
meta
all sites
6.
A
ortho/para
B
meta
all sites
all sites
O
Compound
CH3
|
B
N
S
O
O
B
1.
2.
||
A
||
A
CH3
O
3.
N
B
4.
O
A
O
A
B
N
||
Compound
O
CH3
O
5.
A
CH3
|
N
O
B
6.
O
||
CH3
CH3
A
B
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2.
When given substituents on a benzene ring, as activating or de-activating and as ortho-para
or meta directing for elctrophilic aromatic substitution fill the following by appropriate (✓)
right or (✗) wrong.
Substituent
1.
Activating De-activating Ortho/para
Meta
— OCH 3
O
2.
||
— C — O — CH 3
3.
—O — C — CH 3
||
O
4.
— CH 3
5.
—F
6.
— Ph
7.
O
||
— NH — C — CH 3
8.
O
||
— C — NH — CH 3
9.
— Br
10.
— CN
11.
— CF3
12.
O
||
— C — NH 2
13.
O
||
— C — OH
14.
— CH == CH 2
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569
3.
15.
O
||
- CH = CH - C - OH
16.
O
||
- CH = CH - C - H
17.
– S – Et
18.
- S - Et
||
O
19.
O
||
- S - Et
||
O
20.
–N=O
21.
-CH 2 X
22.
-CHX 2
Devise a series of reactions to convert benzene into meta-chlorobromobenzene.
Select reagents and conditions from the following table, listing them in the order of use.
Compound
Compound
1.
sulphuric acid (conc.)
heat
5.
Mg in ether
2.
Cl 2 + FeCl 3 and heat
6.
PBr 3
3.
NaNO 2 + H 3O (+ ) 0°C
7.
H 3PO 2
4.
H2
Pt catalyst
Compound
9.
Cu 2Br 2 + HBr
10. (CH 3CO) 2 O + Pyridine
HNO 3 (conc.)+
8. H 2SO 4 (conc.) and heat
(a) 1 then 2 then 6
(c) 8 then 4 then 10 then 2 then 3 then 9
(b) 2 then 8 then 4 then 3 then 9
(d) 8 then 2 then 4 then 3 then 9
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570
4.
Match the Column (I) and Column (II). (Matrix)
Column (I)
Column (II)
Cl
N
(a)
C
Cl
C
N
N
(p)
Aromatic
(q)
( 4n + 2)p electron in a single ring
C — Cl
H
N
H—B
B—H
N
N—H
(b)
H
B
H
5.
(c)
Fe(C 5H 5 ) 2
(r)
4np electron in a single ring
(d)
Cr(C 6 H 6 ) 2
(s)
Effective atomic number of metal = 36
Match the Column (I) and Column (II).
Column (I)
Column (II)
Compound (Monocyclic)
Number of p - electron
(a)
C 4 H -42
(p)
2pe
(b)
C 4 H +42
(q)
6pe
(c)
C 9 H +91
(r)
8pe
(d)
C 9 H -91
(s)
10 pe
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6.
Match the Column (I), Column (II) and Column (III). (Matrix)
Column I
7.
Column II
Column III
(a)
(p)
Aromatic
(w)
( 4n + 2)p electron.
n = 0 , 1, 2 , 3
(b)
(q)
Non-aromatic
(x)
4np electron
n = 1, 2 , 3
(c)
(r)
Anti- aromatic
(y)
Non-planar compound
(d)
(s)
Planar compound
(z)
Readily reacts with
active metal
Match the Column (I), Column (II) and Column (III). (Matrix)
Column I
Column II
Column III
(a)
(p)
Readily react with
active metal
(w)
Aromatic
(b)
(q)
Readily undergo
Dimerization at room
temperature
(x)
Anti-aromatic
(c)
–2
(r)
( 4n + 2)p electron
n = 0 , 1, 2 , 3
(y)
Non-aromatic
(d)
+2
(s)
4np electron
(z)
High dipole
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8.
Among the following compound.
Compound
Compound
Compound
N
(a)
(b)
(c)
N
(d)
(e)
N
(f)
OH
+
C 8 H -82
(g)
N
(h)
C 3H +3
(i)
N
(j)
(k)
(l)
N
N
N
(a)
(b)
(c)
(d)
Number of compounds which are aromatic = P
Number of compounds which are anti-aromatic = Q
Number of compounds which are non-aromatic = R
Number of compounds which readily
undergo dimerization at room temperature = S
(e) Number of compound which reacts with active metal = T
Sum of P + Q + R + S + T =
9.
Of the following compounds which will react with Br 2 at room temperature in dark.
(a) Benzene (C 6 H 6 )
(b) Cyclohexene (C 6 H 10 )
(c) Cyclohexane (C 6 H 12 )
(d) Propanoic Acid (C 2H 5CO 2H)
(e) Phenol (C 6 H 5OH)
(f)
Nitrobenzene (C 6 H 5NO 2 )
(g) Hexyne (C 6 H 10 )
(h) 2,2-dichloropropane (C 3H 6 Cl 2 )
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10.
Among the following compound.
Compound
(a)
Compound
(b)
C 8 H -82
Compound
(c)
N
(d)
(e)
(f)
N
N
(g)
(h)
(i)
N
C 3H +31
N
OH
(j)
(k)
(l)
N
(a)
(b)
(c)
(d)
Number of compounds which are aromatic = w
Number of compounds which are non-aromatic = x
Number of compounds which are anti-aromatic = y
Number of compounds which readily undergo Dimerization at room temperature = z
Sum of w + x + y + z = ...
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574
11.
Complete the following table.
Reactant
Reagents(s)/Conditions
Major Organic Products
CH3
(a)
CH2Cl
(A)
NH2
(b)
1. NaNO 2 in dilute
H 2SO 4 0 – 5 ° C
2. heat or boiling
(B)
SO 3 conc. H 2SO 4
(C)
NO2
CH3
(c)
OH
OH
1. NaOH heated at 330°C
2. dilute H 3O +
(D)
(d)
and
CH3
CH3
Cl
NO2
(e)
NO2
1. aqueous NaOH
heated at 60°C
2. dilute H 3O +
(E)
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12. Comprehension
Given is the energy profile diagram of nitration of benzene using mixed acid.
(HNO 3 + H 2 SO 4 ).
T.S1
T.S2
P.E.
(x)
C6H6 + NO2
Ph – NO2
reaction-co-ordinate
A.
Identify (x) in above reaction :
d+
NO2
NO2
(a)
B.
(b)
NO2
H
(c)
d+
H
d+
(d) None
d+
Identify T.S1 in the above reaction.
d+
NO2
(a)
C.
,
(b)
NO2
NO2
H
(c)
d+
H
d+
(d) None
d+
Identify T.S 2 in the above reaction :
d+
NO2
(a)
(b)
NO2
d+
NO2
H
(c)
H
d+
d+
(d) None
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576
13.
Examine the ten structural formulas shown below and select those that satisfy each of the
following conditions. Enter one or more letters (a through j) in each answer box, reflecting
your choice for each.
Compound
Compound
CH3
a.
N(CH3)2
b.
SO3H
c.
NO2
d.
OCH3
e.
f.
H
|
N
O
g.
CH3
|
N – CH3
|
CH3 –
Br
h.
O
i.
CH3
|
C – CH3
|
CH3
Br
j.
A.
Which compounds undergo electrophilic nitration more rapidly than
benzene ?
B.
Which compounds give meta substitution under electrophilic bromination
conditions ?
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577
14.
Nitrobenzene is a versatile compound that may be converted into a wide variety of
substituted benzenes. Five such synthesis are shown below. In each reaction box above an
arrow write letters designating the reagents and conditions, selected from the list at the
bottom of the page, that would effect the transformation. The reagents must be written in
the answer box in the correct order of their use. You may assume appropriate heating or
cooling takes place, and more than one equivalent of the reagent may be used if needed.
Reactant
Reagent
Product
Br
a.
¾¾¾¾®
v.
Cl
CN
b.
¾¾¾¾®
w.
O2N
CH3
NO2
N
c.
¾¾¾¾®
x.
N
O
nitrobenzene
Cl
d.
¾¾¾¾®
CH3
NH2
y.
NH2
Cl
e.
¾¾¾¾®
z.
NH2
H2N
Cl
Reagents
Reagents
A. H 2 , Ni catalyst
F. Cl 2 & FeCl 3
B. KBr & Cu 2Br 2
G. NaOH 10% solution
C. KCN & Cu 2(CN) 2
H. (CH 3CO) 2 O, pyridine
D. HNO 2 0° C
I. HNO 3 H 2SO 4
E. CH 3I & pyridine
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578
15. Match the column I and II.
(a)
Column (I)
Column (II)
Group
Effect on phenyl ring
-CH = CH - CO 2 H
(p)
o/p-directors
(q)
meta-directors
(r)
Activating group
(s)
De-activating group
O
||
(b)
-O - S - CH 3
O
||
(c)
-NH - C - CH 3
- S - CH 3
||
(d)
O
16. Match the column I and II.
N
Column (I)
Column (II)
Group
Effect on phenyl group
O
(a)
(p)
Activating group
(b)
(q)
De-activating group
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579
O–CH=CH2
(c)
(r)
o/p-director
(s)
meta-director
S–Et
(d)
17. Comprehension
Nucleophilic Aromatic substitution (SN Ar ) :
A substituted benzene derivative containing- NO 2 and Cl group at p-position is subjected to
Nu-substitution.
Cl
OCH3
+ CH 3 ONa
CH OH
85°C
¾ ¾3¾¾®
NO2
p-chloronitrobenzene
+ NaCl
NO2
(p-Nitroanisole)
(92%)
A. Match the column I and II :
X
OCH3
CH ONa
¾ ¾3¾¾
®
D
NO2
NO2
Column (I)
X = halogen
Column (II)
relative reactivity toward (SN Ar ).
(a)
–F
(p)
312
(b)
– Cl
(q)
1
(c)
– Br
(r)
0.8
(d)
–I
(s)
0.6
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580
B. If step-2 were rate determining step, which halogen of aryl halide is most reactive toward
SN Ar .
(a) Fluoride
(b) Chloride
(c) Bromide
(D) Iodide
C. Which of the following is most reactive toward SN Ar .
Cl
Cl
NO2
(a)
(b)
NO2
NO2
Cl
Cl
O2N
(c)
NO2
(d)
NO2
NO2
Cl
HNO 3
CH ONa
¾¾¾
¾® ( A) ¾ ¾3¾¾® ( B ) (Major) , product (B) is :
D.
Cl
Cl
Cl
(a)
OCH3
(b)
(c)
Cl
(d)
OCH3
NO2
NO2
NO2
Cl
OCH3
OC H 3
Cl
Cl
NO2
(1) NaOH, D
¾ ¾ ¾ ¾ ¾® (A) , Product (A) is :
E.
I
( 2) H 3O Å
Br
NO2
NO2
ON2
OH
OH
(a)
(b)
(c)
I
OH
Br
(d)
OH
I
I
Br
Br
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581
F. The cumulative effect of their fluorine activate the rings of penta and hexa fluorobenzene
toward nucleophilic aromatic substitution. What is compound X in the following synthesis ?
F
F
F
HOCH CH OH
F
F
F
K CO
2
3
¾ ¾ ¾ 2¾ ¾¾
® ( A) ¾ ¾2 D¾
¾
® ( X ) (C 8 H 4 F4 O 2 )
NaOH, D
F
F
F
O – CH = CH2
F
OH
(a)
F
O – CH2 – CHO
F
H
(b)
F
F
F
F
F
O
F
O
(c)
CH3
(d)
F
F
O
O
F
F
G. Which is the best route for the synthesis of CH3O
NO2 Strating from benzen of ?
NO2
Br
FeBr3
HNO
H 2SO 4
HNO
H 2SO 4
NaOCH
CH 3OH
(a)
2
3
3
3
¾¾
¾
® ¾¾¾
¾
® ¾¾¾
¾
® ¾ ¾ ¾¾
®
(b)
3
3
2
3
¾¾¾
¾
® ¾¾¾
¾
® ¾¾
¾
® ¾ ¾ ¾¾
®
(c)
3
2
3
3
¾¾¾
¾
® ¾¾
¾
® ¾¾¾
¾
® ¾ ¾ ¾¾
®
HNO
H 2SO 4
HNO
H 2SO 4
HNO
H 2SO 4
Br
FeBr3
Br
FeBr3
HNO
H 2SO 4
NaOCH
CH 3OH
NaOCH
CH 3OH
Br2
NaOCH 3
HNO 3
3
(d) ¾ HNO
¾¾
¾
® ¾¾
¾® ¾ ¾ ¾¾
® ¾¾¾
¾®
H 2SO 4
FeBr3
CH 3OH
H 2SO 4
18. Identify product (A) and write its structure.
Ph
|
Ph — CH
|
Ph
+
H
¾ ¾¾
® ( A)
AlCl 3
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582
Subjective Problems
1.
OH
OH
dil.HNO3
A
+
B
More
Less
volatile volatile
2.
3.
(1) Sn|HCl
(2) NaNO2/HCl
C
(mild - basic
condition)
D
Double bond equivalent of D is :
How many isomers 'x' of C 8 H 10 when reacts with hot alkaline KMnO 4 give only aromatic
dicarboxylic acid ? How many isomers 'y' of C 4 H 8 when reacts with hot alkaline KMnO 4 give
carbondioxide ?
Sum of x+y=?
How many groups are o p director in the electrophilic aromatic substitution ?
(i) —NH 2
(v) —OMe
(ix) —N == NH 2
(ii) —COH
O
||
(vi) —O — C — Me
(x) —SO 3 H
(iii)
—N == O
(vii) —Et
(iv)
—COOH
O
||
(viii) — C — NH — Me
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583
ANSWERS — LEVEL 2
1.
Compound
Reactivity
Substitution
1
B
ortho/para
2
A
ortho/para
3
B
ortho/para
4
A
all position
5
B
meta
6
B
ortho/para
2.
Substituent
1.
— OCH 3
O
2.
||
— C — O — CH 3
O
3.
||
—O — C — CH 3
Activating De-activating Ortho/para
Meta
✓
✗
✓
✗
✗
✓
✗
✓
✓
✗
✓
✗
4.
— CH 3
✓
✗
✓
✗
5.
—F
✗
✓
✓
✗
6.
— Ph
✓
✗
✓
✗
7.
O
||
— NH — C — CH 3
✓
✗
✓
✗
8.
O
||
— C — NH — CH 3
✗
✓
✗
✓
9.
— Br
✗
✓
✓
✗
10.
— CN
✗
✓
✗
✓
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584
11.
-CF3
✗
✓
✗
✓
12.
O
||
- C - NH 2
✗
✓
✗
✓
13.
O
||
- C - OH
✗
✓
✗
✓
14.
-CH = CH 2
✓
✗
✓
✗
15.
O
||
- CH = CH - C - OH
✗
✓
✓
✗
16.
O
||
- CH = CH - C - H
✗
✓
✓
✗
17.
– S – Et
✓
✗
✓
✗
18.
- S - Et
||
O
✗
✓
✓
✗
19.
O
||
- S - Et
||
O
✗
✓
✗
✓
20.
–N=O
✗
✓
✓
✗
21.
-CH 2 X
✗
✓
✗
✓
22.
-CHX 2
✗
✓
✗
✓
3.
d
4.
a – p, q; b – p, q; c – p, q,s ; d – p, q, s
5.
a – q; b – p; c – r; d – s
6.
a – p, s – w; b – p, s – w; c – q – x, y, z; d – q – w – y
7.
a – p, q, s – x; b – p – s – y; c – r – w, z; d – r – w, z
8.
P + Q + R + S + T = 18
9.
b, e
10.
w + x + y + z = 14
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585
CH3
OH
CH3
OH
NO2
11.
A – Cl 2 hn or SO 2Cl 2 hn; B –
;C–
NO2
;D–
SO3H
;E–
Cl
NO2
12.
A – a; B – b; C – c
13.
A – a, b, e, f, h; B – c, d, g, i (Note : yet C 6 H 5Br is less reactive than C 6 H 6 but o p directing)
14.
v – F, A, D, B; w – A, H, I, G, D, C; x – A, E, D; y – F, I, A or I, F, A;
z – A, H, I, F, G, A or A, H, I, F, A, G
15.
a – p, s;
b – p, r;
c – p, r; d – p, s
16.
a – p, r;
b – p, r;
c – p, r; d – p, r
17.
A –a – p, b – q, c – r, d – s; B – d; C – d; D – a; E – b; F – c; G – a
18.
Subjective Problems
1. 9
2. 5
3. 6
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586
13
PRACTICAL ORGANIC CHEMISTRY
Level - 1
O
and
1.
O
O
; Compounds (X) and (Y) can be differentiated by :
O
O
(X)
(Y)
(a) H 3O Å , NaOI
(b) H 3O Å , then Fehling test
(c) H 3O Å , then Na
(d) Both (b) and (c)
OEt
2.
Compound CH3 — CH
(P) (Acetal)
and CH 3 – CH 2 – O – CH 2 – CH 3 can be differentiated by :
OEt
( Q)
(a) H 3O Å , Na
(b) H 3O Å , Tollens' test
(c) H 3O Å , Fehling test
(d) All of these
NH2
3.
NH2
and
(aniline)
can be differentiated by :
(cyclohexyl amine)
(a) Hinsberg test
(c) NaNO 2 , HCl, then b-Naphthol
(b) Iso-cyanide test
(d) NaOH
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587
OH
OH
OCH3
4.
(p-methyl anisole)
(p-ethyl phenol)
(p-ethyl benzyl alcohol)
Above compounds can be differentiated by using the reagent:
(a) NaOH, Tollen's reagent, FeCl 3
(b) CrO 3 , Tollen's reagent, FeCl 3
(c) Tollen's reagent, CrO 3 , FeCl 3
(d) Na, Tollen's reagent, FeCl 3
O
O
||
OH
O – C – CH3
O – C – CH3
OH
CO2Et
CO2Et
CO2H
CO2H
5.
Ethyl
salicylate
Salicyclic
acid
acetyl
salicyclic acid
Ethyl
acetyl
Above compounds can be differentiated by the salicylate. Which of the following chemical
test? (used in decreasing order)
(a) NaOH, FeCl 3 , NaHCO 3
(b) aq. NaHCO 3 ,FeCl 3 ,NaOH
(c) NaOI, NaOH, NaHCO 3
(d) NaOH, Na, NaHCO 3
OH
NH2
NO2
CO2H
6.
NO2
(m-nitrophenol)
NO2
(m-nitro benzoic acid)
NO2
NO2
(m-dinitro benzene)
(m-nitro aniline)
Above compounds can be differentiated by which of the following chemical test ? (used in
decreasing order)
(a) NaOH, NaHCO 3 , HCl
(b) HCl, NaOH, NaHCO 3
(c) NaHCO 3 , NaOH, HCl
(d) NaOH, HCl, NaHCO 3
CH2MgBr
7.
CH3
CO2Na
I2
(i) CH 3CHO
¾ ¾¾¾¾® (A) ¾ ¾¾
®
NaOH
+ CHI 3 ,
(ii)NH 4Cl
Product (A) in the above reaction is :
CH3 OH
CH – CH3
(a)
OH
|
(c) Ph — CH 2 —CH — CH 3
CH3
CH2 – CH 3
(b)
CH3 O
C – CH3
(d)
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NH3Cl–
NO2
Cl
8.
and
(Q)
(P)
Above compounds (P) & (Q) can be differentiated by :
(a) amm. AgNO 3
(b) NaOH
(c) FeCl 3
(d) Both (a) & (b)
9.
10.
Which of following acid give positive Tollen's reagent test.
CO2H
CO2H
CO 2H
(a) (CH2)2
(b) CH2
(c) |
CO2H
CO2H
CO 2H
Which of following compounds give positive Tollen's test?
O
OCH3
O
OH
O
(a)
(b)
(c)
OCH3
(d) HCO 2H
O
(d)
OH
11.
Give a simple test to differentiate cyclohexane and cyclohexene
(a) Br 2 H 2O
(b) Bayer’s reagent
(c) Tollen’s reagent
(d) Both (a) and (b)
12.
Give test to differentiate (Bromobenzene) Ph – Br and benzyl bromide (PhCH 2Br).
(a) (i) aq. KOH (ii) Na
(b) AgNO 3
(c) KMnO 4
(d) All these
13.
Give test to differetiate 1,1-dichloroethane and 1, 2-dichloroethane :
(a) 2,4 -DNP then aq. KOH
(b) aq. KOH then 2, 4-DNP
(c) NaHSO 3
(d) Lucas reagent
14.
Test to differentiate between (CH 3OH) and (Ph – OH) is/are :
(methanol)
(a) Litmus test
(c) Br 2 H 2O
(Phenol)
(b) FeCl 3
(d) All of these
15.
Acetaldehyde and benzaldehyde can be differentiated by :
(a) Fehling test
(b) Iodoform test
(c) Tollen’s reagent
(d) both (a) and (b)
16.
Ethylamine and diethylamine cannot be differentiated by :
(a) Hinsberg test
(b) carbylamine test
(c) Iodoform test
(d) both (a) and (b)
17.
Lassaigne’s test for the detection of nitrogen will fail in the case of :
(a) NH 2CONH 2
(b) NH 2CONHNH 2 .HCl
(c) NH 2NH 2 .HCl
(d) C 6 H 5NHNH 2 . 2HCl
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589
18.
Sodium nitroprusside when added to an alkaline solution of sulphide ions produces a
colouration which is :
(a) red
(b) blue
(c) brown
(d) purple
19.
In Kjeldahl’s method, nitrogen present is estimated as :
(a) N 2
(b) NH 3
(c) NO 2
(d) none of these
20.
In Kjeldahl’s method of estimation of nitrogen, K 2SO 4 acts as :
(a) an oxidising agent
(b) catalytic agent
(c) hydrolysing agent
(d) boiling point elevator
21.
The prussian blue colour obtained during the test of nitrogen by Lassaigne’s test is due to the
formation of :
(a) Fe[Fe(CN) 6 ]3
(b) Na 3[Fe(CN) 6 ]
(c) Fe(CN) 3
(d) Na 4 [Fe(CN) 5 NOS]
22.
A compound which does not give a positive test in Lassaigne’s test for nitrogen is:
(a) urea
(b) hydrazine
(c) azobenzene
(d) phenyl hydrazine
23.
p-nitrophenol and o-nitrophenol are separated by :
(a) distillation
(b) steam distillation
(c) crystallization
(d) fractional crystallization
24.
Which of the following reagent is used for the separation of acetaldehyde from
acetophenone ?
(a) NH 2OH
(b) NaOI
(c) Tollen's reagent (d) C 6 H 5NHNH 2
25.
The formula of gas is [CO] x . If its vapour density is 70, the value of x will be :
(a) 2.5
26.
(b) 3.0
(c) 5.0
The structure of the monomer that would give the following polymer by an addition
mechanism is :
CO2Me
CO2Me
CO2Me
CO2Me
(a)
(c)
27.
(d) 6.0
CO2Me
CO2Me
(b)
(d)
CO2Me
CO2Me
Identify the correct set of stereochemical relationships amongst the following
monosaccharides I – IV
OH
OH
OH
OH
O
(I)
OH
HO
OMe
OH
(II)
HO
O OMe
O
HO
OH
OMe
(III)
OH
(IV)
HO
OH
OH
O OMe
OH
OH
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590
(a)
(b)
(c)
(d)
28.
I and II are anomers ; III and IV are epimers
I and II are epimers ; III and IV are anomers
I and III are anomers ; I and II are epimers
I and III are epimers ; II and IV are anomers
A dye, phenolphtnalein is prepared by reacting phenol with phthalic anhydride in acidic
medium. It give pink colour in alkaline medium due to extended conjugation in a new
complex formed (phthalein - dye test) identify the complex A :
O
O
s
¾OH
¾® ( A) Product ; The structure of ( A) is:
OH
OH
Phenophthaline
O
O
Os
Os
(a)
(b)
OH
OH
O
O
O
Os
(c)
(d) None
O
OH
ANSWERS — LEVEL 1
1.
(d)
2.
(d)
3.
(c)
4.
(b)
5.
(b)
6.
(c)
7.
(a)
8.
(d)
9.
(d)
10.
(c)
11.
(d)
12.
(d)
13.
(b)
14.
(d)
15.
(d)
16.
(c)
17.
(c)
18.
(b)
19.
(b)
20.
(d)
21.
(d)
22.
(b)
23.
(a)
24.
(c)
25.
(c)
26.
(c)
27.
(c)
28.
(b)
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591
Level - 2
1. Comprehension
O
O
C – O – Et
(a)
CHO
CO2H
O–H
C – CH3
CH2 – CHO
OCH3
CH3
O – CH = CH2
O–H
OH
(b)
(c)
(d)
(e)
(f)
A.
Which isomer gives positive iodoform test ?
(a) a
(b) b
(c) d
(d) e
B.
Which isomer gives +ive Tollen’s test, also reacts with FeCl 3 ?
(a) b
(b) f
(c) c
(d) d
C.
Which isomer reacts with NaHCO 3 ?
(a) c
(c) e
D.
2.
(b) d
(d) f
Which isomer on hydrolysis gives 1, 4-di hydroxybenzene ?
(a) a
(b) d
(c) e
(d) f
O
||
14
NaHCO 3
Na
® ( A) gas ; Ph — OH ¾ ¾
¾® ( B )gas
Ph — C — OH ¾ ¾¾¾
Sum of molecular mass of gas (A+B=?)
ANSWERS — LEVEL 2
1.
A – d; B – b; C – a; D – b
2.
48
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592
14
BIOMOLECULES
Level - 1
1.
Which statement correctly completes the statement ?
Except for glycine, which is achiral, all the amino acids present in proteins ......
(a) are chiral, but racemic
(b) have the L configuration at their a carbon
(c) have the R configuration at their a carbon
(d) have the S configuration at their a carbon
2.
Assume that a particular amino acid has an isoelectric point of 6.0. In a solution at pH 1.0,
which of the following species will predominate ?
R
R
|
+ |
(b) H 2NCH CO 2H
(a) H 3NCH CO 2H
R
R
|
+ |
(d) H 2NCH CO –2
(c) H 3NCH CO –2
3.
The pK a values for the three ionizable groups X, Y and Z of glutamic acid are 4.3, 9.7 and 2.2
respectively
H O 2C — CH 2 —CH — CO 2 H
X
|
Z
+NH 3
The isoelectric point for the amino acid is :
(a) 7.00
(b) 3.25
(c) 4.95
(d) 5.95
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4.
R
|
An amino acid may be represented by general formula H 2N – CH – COOH . If R = - CH 2C 6 H 5
then it is phenylalanine (Phe) and if R = CH 3 then it is alanine (Ala). Find the sequence of
reagents from those given below to synthesize Phe - Ala.
CH 3
CH 3
|
|
(2) H 2NCHC O 2CH 2C 6 H 5
(1) ZNHCHCO 2H
CH 2C 6 H 5
CH 2C 6 H 5
|
|
(4) H 2N CHCO 2CH 2C 6 H 5
(3) ZNH CHCO 2H
(a) 1 and 2
5.
6.
(b) 1 and 4
(c) 2 and 3
(d) 3 and 4
Iso-electric point of alanine is (pH = 6). At which pH, maximum concentration of zwitter ion
of alanine will be present ?
(a) pH > 6
(b) pH < 6
(c) pH = 6
(d) pH = 7
O
||
NH 2 – CH – C – NH – CH 2 – CO 2H
|
CH 3
Identify the amino acid obtained by hydrolysis of the above compound:
(a) Glycine
(b) Alanine
(c) Both (a) and (b) (d) None of these
7.
At iso-electric point :
(a) conc. of cation is equal to conc of anion
(b) Net charge is zero.
(c) Maximum conc. of di-polar ion (Zwitter ion) will be present
(d) All of the above
8.
Which of following amino acid has lowest iso-electric point ?
(a) Glycine
(b) Alanine
(c) Aspartic acid
9.
Find iso-electric point of given amino acid
CH 3 — CH — CO 2H
|
NH 3
(d) Lysine
pK a = 2.2
Å
(a) 3.3
10.
(b) 5.9
pK b = 4.4
(c) 9.6
(d) 11.8
Find iso-electric point of the given amino acid
O
||
H – O – C – CH 2 – CH 2 – CH – CO 2H (pK a = 2)
|
N H3
Å
(pK a = 4)
(pK a = 9)
(a) 5.5
(b) 6.5
(c) 3
(d) 5
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11.
(1) NH 3 + HCN
HgSO 4
( B ); Product (B) of given reaction is :
H – C º C – H ¾¾¾¾®( A) ¾¾¾¾¾®
Å
H 2SO 4
(2) H 3O
(a) Glycine
(c) valine
12.
13.
(b) Alanine
(d) Leucine
Which amino acid does not contain chiral centre ?
(a) Valine
(b) Leucine
(c) Glycine
Which of the following is Sanger reagent ?
(a) 2,4-Di-nitro flurobenzene
(c) 2, 4-Di-nitro chlorobenzene
(d) Iso-leucine
(b) Phenyl isocyanate
(d) 2, 4-Di-nitro iodobenzene
14.
A D-carbohydrate is :
(a) Always dextrorotatory
(b) Always laevorotatory
(c) Always the mirror of the corresponding L-carbohydrate
(d) None of these
15.
Which L-sugar on oxidation gives an optically active dibasic acid (2 COOH groups) ?
CHO
H
(a)
CHO
OH
HO
H
HO
H
H
CHO
OH
(b) HO
H
OH
(c) H
OH
H
OH
H
CH2OH
CHO
H
CH2OH
HO
OH
H
(d)
OH
H
HO
CH2OH
H
CH2OH
CH == N — NH — Ph
C == N — NH — Ph
16.
HO
H
The given osazone can be obtained by :
OH
OH
H
H
CH2OH
(a) D-glucose
(b) D-mannose
(c) D-Idose
(d) Both (a) & (b)
17.
Which of the following pair gives same phenyl osazone ?
(a) D-Glucose and D-Allose
(b) D-Glucose and D-Alfrose
(c) D-Glucose and D-Mannose
(d) D-Glucose and D-Talose
18.
Which of the following is the Fischer projection of L-threonine (also known as (2S, 3R)2-amino-3-hydroxybutanoic acid) ?
CO2H
H
(a) H
NH2
OH
CH3
CO2H
(b)
H2N
H
H
OH
CH3
CO2H
H
(c) HO
NH2
H
CH3
CO2H
H2N
(d) HO
H
H
CH3
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19.
20.
21.
Among the three compounds shown below, two yield the same product on reaction with
warm HNO3. The exception is :
CHO
CHO
CHO
HO
H
HO
H
H
HO
H
H
(a) H
(b) HO
(c) HO
(d) None of these
OH
OH
H
OH
H
OH
H
CH3
CH2OH
CH2OH
The optical rotation of the a- form of a pyranose is + 150.7º, that of the b- form is + 52.8º. In
solution an equilibrium mixture of these anomers has an optical rotation of + 80.2º. The
percentage of the a-form in equilibrium mixture is :
(a) 28%
(b) 32 %
(c) 68%
(d) 72%
Which of the following represents the anomer of the compound shown ?
H
HOCH2 O
H
H
H
OH
HO
HOCH2
(a)
H
OH
H
H
(c)
22.
(b)
OH
OH
O
H
H
H
H
HO
OH
OH
OH
O
OH
HOCH2
HOCH2
H
O
H
OH
HO
(d) None of these
H
H
H
Which set of terms correctly identifies the carbohydrate shown ?
CH2OH
O
H
(1)
(5)
(a)
(c)
Pentose
Aldose
2, 6, 8
1, 5, 8
HO
(2) Pentulose
(6) Ketose
H
OH
OH
(3)
(7)
(b)
(d)
Hexulose
(4) Hexose
Pyranose
(8) Furanose
2, 6, 7
A set of terms other than these
23.
For the complex conversion of D-glucose into the corresponding osazone, the minimum
number of equivalents of phenyl hydrazine required is :
(a) two
(b) three
(c) four
(d) five
24.
Which one of the following compounds will form an osazone derivative ?
(a) CH 3CH 2COCH 2OH
(b) CH 3COCH 2CH 2OH
(c) CH 3CH 2CHOHCH 2OH
(d) CH 3CH 2COCH 2OCH 3
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25.
Which of the following structure is L-arabinose?
CHO
H
OH
OH
HO
(a) H
H
CHO
H
OH
H
HO
(b) H
HO
CH2OH
26.
CHO
OH
H
H
H
HO
(c)
HO
CH2OH
HO
HO
(d) H
H
CHO
H
H
OH
OH
CH2OH
CH2OH
Which one of the statements concerning the equilibrium shown is true ?
HOCH2
H
HO
H
H
O
HO
H
OH
OH
H
HO
HOCH2
O
H
HO
H
OH
H
OH
(a) The two structures are enantiomers of each other. They have equal but opposite optical
rotations and recemize slowly at room temperature
(b) The two structures are enantiomers of each other. They racemize too rapidly at room
temperature for their optical rotations to be measured
(c) The two structures are diastereomers of each other. Their interconversion is called
mutarotation
(d) The two structures are diastereomers of each other. Their interconversion does not
require breaking and making bonds, only a change in conformation
27.
The configurations of the chirality centres in D-threose (shown) are :
CHO
HO
H
H
OH
CH2OH
(a) 2R, 3R
(b) 2R, 3S
(c) 2S, 3R
(d) 2S, 3S
28.
Rapid interconversion of a-D-glucose and b-D-glucose in solution is known as :
(a) racemization
(b) asymmetric induction
(c) fluxional isomerization
(d) mutarotation
29.
Identify the correct set of stereochemical relationships amongst the following
monosaccharides I-IV.
OH
OH
O
OH
OH
OMe
OMe
OH
(I)
OH
O OMe
OH
OH
(a)
(b)
(c)
(d)
OH
O
OH
O OMe
OH
OH
OH
OH
(II)
OH
(III)
OH
(IV)
I and II are anomers ; III and IV are epimers
I and III are epimers ; II and IV are anomers
I and II are epimers ; III and IV are anomers
I and III are anomers ; I and II are epimers
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30.
What is the structure of L-glucose ?
CHO
CHO
HO
H
(a)
HO
HO
H
OH
H
H
H
HO
(b)
H
H
H
HO
(c)
H
HO
CH2OH
CH = O
H
CH2 – OH
H
(c) HO
H
(b) HO
OH
(d) None of these
CH2 – OH
What is the structure of L-glyceraldehyde?
H–C=O
(a) HO – CH2
OH
H
OH
H
CH2 – OH
CH2OH
31.
OH
H
OH
OH
CHO
(d) Both (a) and (b)
H–C=O
HC – OH
C – OH
32.
HO
H
H
H , the given is enol form of :
OH
OH
CH2OH
(a) D-glucose
33.
HO-
(b) D-mannose
(c) D-fructose
(d) All of these
34.
D-glucose
A + B; A and B are :
(a) D-mannose & D-mannitol
(b) D-mannose & D-Fructose
(c) D-Allose & D-Altrose
(d) D-Glucose & D-Idose
Stereoisomers of aldoheptose is (a) and stereoisomers of ketoheptose is (b).
Ratio of a/b is :
1
2
4
1
(a)
(b)
(c)
(d)
2
1
1
4
35.
D-Glucose ¾¾¾®
( A); Product (A) is :
D
36.
37.
38.
HNO 3
(a) D-Gluconic acid (b) D-Glucitol
(c) D-Fructose
(d) D-Glucaric acid
D-glucose & D-fructose can be differentiated by :
(a) Fehling solution (b) Tollens reagent (c) Benedict test
(d) Br 2 H 2O
D-Glucose exist in x different forms. The value of x (stereoisomer) is :
(a) 2
(b) 3
(c) 4
(d) 5
HO-
HO-
D-Mannose
D-Glucose
(A) ;
Product (A) of above reaction is
(a) D-glucose
(b) D-fructose
(c) D-talose
(d) D-idose
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39.
Which of the molecules below will react with Ag + ?
HO
(i) HO
HO
HO
O
CH2OH
HO
O
OH
HO
OH
OH
HO
OH
OH
O
OH
O
(iv)
O
O
OH HO
HO
CH2OH
OH
OH
HO
HO
HO
HO
O
(v) HO
HO
OCH2CH3
(vi)
(b) (ii) and (iv)
(c) (iv) and (vi)
OCH3
OH OH
O
O
OH
OH
(d) (i), (ii), (iii) and (vi)
OH
O
O
HO
HO
HO
HO
O
HO
HO
A.
CH2
OH
(a) (i), (iii) and (v)
40.
NHCH2CH2
HO
OH
O
O
(ii)
OCH3
(iii) HO
HO
OH
H2N
O
OH
HO
O
HO
OH
OH
HO
O
B.
HO
HO
HO
C. HO
HO
OH
O
HO
O
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OH
OH
O HO
O
OH
HO
O
O
OH
OH
OH
D.
O
O
OH
OH
OH
Which of the compounds (A-D) depicted above is NOT a hemiacetal linkage ?
(a) Compound A
(b) Compound B
(c) Compound C
(d) Compound D
(e) None of the above (they are all hemiacetals)
41.
Which of the following Fischer projection formula is same as D-Glyceraldehyde ?
CH2OH
CH2OH
CHO
CHO
(b) H
(c) OH
CHO
OH
CH2OH (d) H
CH2OH
CHO
H
H
HO
What is the structure of the monomer from which the following polymer was made ?
Ph
Ph
Ph
Ph
(a) OH
42.
[
(b) Ph
(a) Ph
(c) Ph
43.
Ph
(d) Ph
Ph
The following structure represents a subunit of a hydrocarbon polymer that may be prepared
by a radical polymerization method. Identify the monomer that has been polymerized to
make this polymer chain.
(a)
44.
]
n
(b)
(c)
(d)
Choose the answer that has correctly identified the number of acetals and hemiacetals in
isomaltose.
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H
O
..
..
O
OH
HO
HO
OH
O
HO
OH
O
HO
isomaltose
Acetal
(a) 0
(c) 0
45.
Hemiacetal
0
1
Acetal
(b) 1
(d) 1
Hemiacetal
0
1
Predict the product of the following reaction.
HO
O
HO
OH
, H+
¾ MeOH
¾¾¾
¾®
OH
HO
HO
HO
(a)
O
HO
OMe
OH
(b)
O
HO
HO
HO
HO
(c)
O
HO
OH
OH
(d)
O
47.
OH
OH
MeO
MeO
46
OH
OMe
HO
HO
Which reagent/s can be used to distinguish glucose and fructose ?
(I) Bromine water
(II) Tollen’s reagent (III) Schiff’s reagent
(a) (I), (II) and (III) (b) (II) and (III)
(c) Only (I)
(d) Only (III)
Choose the peptide that matches the abbreviation Phe-Val-Ala.
O
O
O
H
H
H2N—CHC—N—CHC—N—CHC—OH
O
O
O
H
H
H2N—CHC—N—CHC—N—CHC—OH
CH2
CHCH3
CH3
(a)
CH2
CH3
O
O
H
H
H2N—CHC—N—CHC—N—CHC—OH
CH2
(c)
CH3
O
O
O
H
H
H2N—CHC—N—CHC—N—CHC—OH
CHCH3
CH3
CH2
CH3
(b)
O
CHCH3
CH3
(d)
CH2
CHCH3
CH3
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48.
(I)
Which of the following carbohydrate(s) would not undergo mutarotation in aqueous
solution?
CH2OH
CH2OH
CH2OCH3
OCH3
CH2OH
O
OCH3
OH
OH
O
O
O
OH
OH
OH
(IV)
(III)
(II)
OH
49.
OH
OH
OH
OH
OH
(a) II only
(b) I, III and IV only (c) II and IV only
The number of peptide bonds in the compound.
CH3
O
O
H
N
NHNH2
H
H3C
N
H3C
CH3
50.
(a) 1
(b) 2
(c) 3
(d) 4
Serine (HOCH 2CH(NH 2 )COOH) is an essential amino acid. The correct Fisher projection of
serine is
NH2
H
OH
(a) H
(b) HOH2C
CH2OH
COOH
CH2OH
(c) H
OH
(d) I and III only
NH2
COOH
COOH
COOH
(d) H2N
H
NH2
CH2OH
ANSWERS — LEVEL 1
1.
(b)
2.
(a)
3.
(b)
4.
(b)
5.
(c)
6.
(c)
7.
(d)
8.
(c)
9.
(b)
10.
(c)
11.
(b)
12.
(c)
13.
(a)
14.
(d)
15.
(a)
16.
(d)
17.
(c)
18.
(b)
19.
(b)
20.
(a)
21.
(b)
22.
(a)
23.
(b)
24.
(a)
25.
(c)
26.
(c)
27.
(c)
28.
(d)
29.
(d)
30.
(a)
31.
(d)
32.
(d)
33.
(b)
34.
(b)
35.
(d)
36.
(d)
37.
(b)
38.
(b)
39.
(c)
40.
(e)
41.
(c)
42.
(b)
43.
(c)
44.
(d)
45.
(a)
46.
(c)
47.
(a)
48.
(c)
49.
(a)
50.
(d)
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602
Level - 2
1.
Match the Column (I) and Column (II). (Matrix)
Column (I)
Molecule
Column (II)
Configuration
CHO
(a)
H
OH
(p)
R- (Rectus)
(q)
S- (Sinister)
(r)
D
(s)
L
CH2OH
CHO
(b)
HO
H
CH2OH
NH2
(c)
H
CO2H
CH3
NH2
(d)
CH3
H
CO2H
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2. Comprehension
A
CH2OH
OH
C
O
B
OH
F
OH
E
OH
D
One cyclic acetal form of D-galactose is shown above.
A.
Which atom is the anomeric carbon ?
(a) Atom A
(b) Atom B
(e) Atom E
(f) Atom F
(c) Atom C
(d) Atom D
B.
Which name most completely describes this cyclic acetal form ?
(a) a-D-Galactofuranose
(b) b -P- Galactofuranose
(c) a-D- Galactopyranose
(d) b -D- Galactopyranose
3.
How many compound which is given below is isomer of D-Glucose ?
D-Mannose, D-Fructose, D-Gulose, D-Idose, D-Galactose, D-Arabinose, D-Ribose.
4.
How many acidic group is present in given amino acid ?
r
NH3—CH—CH2—CH2—CO2H
CO–
2
ANSWERS — LEVEL 2
1.
a – p, r; b – q, s; c – q, s; d – p, r
2.
A – f; B – c
3.
5
4.
2
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15
IUPAC NAME
Level - 1
O
1.
Cl
Br
C—OH
I
Total number of substituent present in the above compound :
2.
(a) 1
(b) 2
(c) 3
(d) 4
CH IUPAC name will be :
(a) Hex-5-en-1-yne
(c) Hex-6-en-1-yne
CH3
3.
IUPAC name of
(b) Hex-1-en-5-yne
(d) Hex-1-en-6-yne
CH3
OEt
is :
(a) 1-Ethoxy-2, 2-dimethylcyclohexane
(b) 2-ethoxy-1, 1-dimethyl cyclohexane
(c) 1, 1-Dimethyl-2-ethoxycyclohexane
(d) 2-methyl-1, 1-ethoxy cyclohexane
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4.
How many secondary carbon and hydrogen atoms are present in the molecule given below
respectively ?
Br
Br
(a) 2, 3
5.
(b) 2, 2
(c) 3, 3
(d) 2, 0
Which IUPAC name is correct for the given compound ?
OHC
CH3
CH3
6.
(a) 3, 7-dimethylocta-2, 6-dienal
(b) 2, 6-dimethyloct-2, 6-dienal-8
(c) 7-formyl-2, 6-dimethylhept-2, 6-diene
(d) 7-aldo-2,6-dimethylhept-2, 6-diene
Write the IUPAC name of the following compound :
CO—O—C2H5
CO—Cl
(a) ethyl-2-(chlorocarbonyl) benzoate
(b) ethyl-2-(chlorocarbonyl) hexanoate
(c) 2-(thoxycarbonyl) benzoyl chloride
7.
(d) None of these
CH2CH3
Cl
C == C
The IUPAC name of the compound
is :
I
H3C
(a) trans-2-chloro-3-iodo-2-pentene
(b) cis-2-chloro-3-iodo-2-pentene
(c) trans-3-iodo-4-chloro-3-pentene
8.
The IUPAC name of the compound is :
CONH2
(d) cis-3-iodo-4-chloro-3-pentene
CHO
(a) 2-methyl-6-oxohex-3-enamide
(b) 6-keto-2-methyl hexanamide
(c) 2-carbamoylhexanal
(d) 2-carbamoylhex-3-enal
F
9.
The IUPAC name of
is:
I
Cl
Br
(a) 1-Bromo-2-chloro-3-fluoro-6-iodo benzene
(b) 2-Bromo-1-chloro-5-fluoro-3-iodo benzene
(c) 4-Bromo-2-chloro-5-iodo-1-fluoro benzene
(d) 2-Bromo-3-chloro-1-iodo-5-fluoro benzene
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O
10.
The IUPAC name of CH3—CH2—CH—C—OCH3 is:
C2H5
11.
(a) Methyl 2-ethylbutanoate
(b) 1-methoxy-2-ethylbutanone
(c) 3-Methoxycarbonylpentane
(d) 1-methoxy-2-ethylbutanal
O
||
The IUPAC name of CH 3 — CH == CH — C — OH is:
(a) But-1-en-4-oic acid
(b) 1-hydroxybut-2-en-1-one
(c) But-2-en-1-oic acid
(d) But-2-en-4-oic acid
OCH3
12.
The IUPAC name of CH3—CH ==C—CH 3 is:
(a) 1-Methoxy-1-methylpropene
(b) 2-Methoxybut-2-ene
(c) dimethylpropeneether
(d) none of these
Me O
13.
The IUPAC name of CH2 ==C—C—OC 2H 5 is:
(a) Ethyl 2-methylprop-2-enoate
14.
(b) Ethyl 2-methylprop-1-enoate
(c) 1-Ethoxy-2-methylprop-2-enone
(d) 1-Ethoxy-2-methylprop-2-enal
CH 3 CH 3
|
|
The IUPAC name of CH 3 — CH — CH — CH 2 NH 2 is:
(a) 2, 3-Dimethylbutan-4-amine
15.
(b) 2, 4-Dimethylbutan-1-amine
(c) 2,4-Dimethylbutan-4-amine
(d) 2, 3-Dimethylbutan-1-amine
O
||
The IUPAC name of CH 3 — C — CH — CH — CH 3 is:
|
|
C 2H 5 CH 3
(a) 3-(Methylethyl) pentan-2-one
(b) 3-(Methylethyl)pentan-4-one
(c) 3-Ethyl-4-methylpentan-2-one
(d) 3-Ethyl-2-methylpentan-4-one
O
16.
The IUPAC name of CH3—CH—CH2—C—Br is:
CH3
(a) 2-Methylbutanoyl bromide
(b) 2-Methylbutan-4-oyl bromide
(c) 1-Bromo-3-Methylbutanone
(d) 3-Methylbutanoyl bromide
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17.
18.
The IUPAC name of CH 3 — CH — CH 2 — OH is:
|
C 6H 5
(a) 2-Phenylpropan-1-ol
(b) 2-Phenylpropan-3-ol
(c) 1-(2-Hydroxy-1-methylethyl) benzene (d) 1-((Hydroxymethyl)ethyl) benzene
CH 3
|
The IUPAC name of CH 3 — C — CH — CH — CH 2 — CH 3 is:
|
|
|
CH 3 CH 3 I
(a) 3-Iodo-4,5,5-trimethylhexane
(b) 4-Iodo-1, 1, 3-trimethylhexane
(c) 4-Iodo-2, 2-dimethylheptane
19.
20.
(d) 4-Iodo-2, 2, 3-trimethylhexane
CH 3
|
The IUPAC name of CH 3 — CH 2 — CH — CH — C — CH 3 is:
|
|
|
CH 3 OH
Cl
(a) 4-Chloro-2, 3-dimethylhexane-2-ol
(b) 4-Chloro-2-hydroxy-2, 3-dimethylhexane
(c) 4-Chloro-1, 1, 2-trimethylpentan-2-ol
CH3
(d) 3-Chloro-2, 3-dimethylhexane-2-ol
CH—CHO is:
The IUPAC name of
(a) 2-Phenylpropan-3-al
(b) Formylethylbenzene
(c) 2-Phenylpropanal
(d) Ethylformylbenzene
O
21.
22.
The IUPAC name of CH3—C—CH
is:
CH3
(a) 2-Methylbutan-3-one
(b) 3-Methylbutan-2-al
(c) 2-Methylbutan-3-al
(d) 3-Methylbutan-2-one
The IUPAC name of
CH3—CO
CH3—CH2—CO
(a) Ethanoic propanoic anhydride
(c) 1-Ethanoyloxypropanone
23.
CH3
O is:
(b) Propanoic ethanoic anhydride
(d) 3-Ethanoyloxypropan-3-one
The IUPAC name of CH 3 — CH — CH — CH 2 — OH is:
|
|
OH
C 2H 5
(a) 3-Ethylbutane-2, 4-diol
(b) 2-Ethylbutane-1, 3-diol
(c) 3-Ethylbutane-1, 3-diol
(d) 2-Ethyl-1-methylpropane-1, 3-diol
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24.
The IUPAC name of CH 3 — C — C — CH 3 is:
|| ||
O O
(a) Butane-2, 3-dial
(b) Butane-1, 3-dione
(c) Butane-2, 3-dione
25.
The IUPAC name of CH 2 == CH — CH == CH 2 is:
(a) Butane
26.
(d) 1, 2-dimethylethanedione
(b) Buta-1, 3-diene
The IUPAC name of CH 2 — CH 2 — CH 2 is:
|
|
COOH
COOH
(a) Pentane-1, 5-dioic acid
(b) Pentane-1, 5-dicarboxylic acid
(c) Propane-1, 3-dioic acid
27.
28.
29.
(c) Butane-1, 3-diene (d) none of these
(d) none of these
The IUPAC name of CH 2 — CH == CH — CHO is:
|
CHO
(a) propene-1, 3-dial
(b) Propene-1, 3-dicarbaldehyde
(c) Pent-3-ene-1, 5-dial
(d) Pent-2-ene-1, 5-dial
The IUPAC name of CH 2 — CN is:
|
CH 2 —CN
(a) Butane-1, 4-dicarbonitrile
(b) Ethane-1, 2-dicarbonitrile
(c) Ethane-1, 2-dinitrile
(d) Butane-1, 4-dinitrile
The IUPAC name of CH 2 — CH — CH 2 — CH 2 is:
|
|
|
CH 3
NH 2
NH 2
(a) 2-Methylbutane-1, 4-diamine
(b) 3-Methylbutane-1, 4-diamine
(c) 3-(Aminomethyl)butanamine
(d) 2-(Aminomethyl)butan-4-amine
30.
CH 2Cl
|
The IUPAC name of CH 2 — CH — CH 2 is:
|
|
Cl
Cl
(a) Tris(chloromethyl) methane
(b) 1, 3-Dichloro-2 (chloromethyl) propane
(c) 1-Chlorobis(chloromethyl) ethane
(d) none of these
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31.
CH 3
|
The IUPAC name of CH 3 — CH — CH — CH — C — CH 3 is:
|
|
|
|
CH 3
OH
CH 3 OH
(a) 3, 5, 5-Trimethylhexane-2, 4-diol
(b) 2, 2, 4-Trimethylhexane-3, 5-diol
(c) 1, 2, 4, 4-Tetramethylpantane-1, 3-diol (d) 2, 2, 4, 5-Tetramethylpantane-3, 5-diol
32.
33.
34.
35.
The IUPAC name of HOOC — CH == CH — COOH is:
(a) But-2-ene-1, 4-dicarboxylic acid
(b) But-2-ene-1, 4-dioic acid
(c) Ethene dicarboxylic acid
OCH 3
|
The IUPAC name of CH 3 — CH — CHO is:
(d) Ethene dioic acid
(a) 1-Formyl-1-methoxyethane
(b) 2-Methoxypropan-3-one
(c) 2-Methoxypropanal
(d) 2-Methoxypropan-3-al
CH 3
|
The IUPAC name of CH 2 == C — COOCH 3 is:
(a) Methyl-2-methylprop-1-en-3-oate
(b) 2-Methoxycarbonylpropene
(c) 2-Methoxycarbonylprop-2-ene
(d) Methyl-2-methylprop-2-enoate
The IUPAC name of CH 3 — CH == CH — COOH is:
(a) But-2-ene-1-oic acid
36.
37.
(b) But-1-ene-1-oic acid
(c) But-2-ene-1-carboxylic acid
(d) Propene-1-carboxylic acid
OH
|
The IUPAC name of CH 3 — CH — COOH is:
(a) 2-Hydroxypropanoic acid
(b) 1-Hydroxypropanoic acid
(c) 1-Hydroxyethane carboxylic acid
(d) 1-Hydroxyethanoic acid
The IUPAC name of HO — CH — COOH is:
|
HO—CH—COOH
(a) 2, 3-Dihydroxybutane-1, 4-carboxylic acid
(b) 2, 3-Dihydroxybutane-1, 4-dioic acid
(c) 1, 2-Dihydroxyethane dicarboxylic acid
(d) none of these
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38.
39.
40.
The IUPAC name of
is:
(a) 3-Methyl-2-oxobutanecarboxylic acid
(b) 2-Methyl-3-oxobutan-4-oic acid
(c) 3-Methyl-2-oxobutanoic acid
(d) 3-Methyl-1,2-dioxobutanoic acid
The IUPAC name of NC — CH 2 — CH 2 — COOH is:
(a) 3-Carboxy propanenitrile
(b) 4-Cyanobutanoic acid
(c) 2-Cyanoethane Carboxylic acid
(d) 3-Cyanopropanoic acid
The IUPAC name of
is:
(a) 3-Carboxy-3-hydroxypentanedicarboxylic acid
(b) 2-Hydroxypropane-1, 2, 3-tricarboxylic acid
(c) 2-Hydroxypropane-1, 2, 3-trioic acid
(d) 3-Hydroxypropane-1, 2, 3-tricarboxylic acid
41.
O
||
The IUPAC name of CH 3 — C == CH — CH 2 — C is:
|
|
OH
COOC H
2
5
(a) 4-ethoxycarbonylpent-3-enoic acid
(b) 4-ethanoyloxypent-3-enoic acid
(c) 3-ethoxycarbonylbut-2-enecarboxylic acid
(d) 3-ethoxycarbonylpent-3-enoic acid
42.
The IUPAC name of CH 3 — CH — C — C — NH is:
|| || |
|
Br
CH 3 O O
(a) (N-Bromo)-2-keto-3-methylbutanamide
(b) (N-Bromo)-2-keto-4-methylbutanamide
(c) (N-Bromo)-1, 2-diketo-3-methylbutanamine carboxamide
(d) (N-Bromo)-1-keto-2-methylpropane
43.
The IUPAC name of CH 2 — C == CH — CH 2 OH is:
|
|
Cl
CH 3
(a) 4-Chloro-3-methylbut-2-en-1-ol
(b) 1-Chloro-2-methylbut-2-en-4-ol
(c) 4-Chloro-1-hydroxy-3-methylbut-2-ene
(d) 1-Chloro-4-hydroxy-2-methylbut-2-ene
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611
44.
O
||
The IUPAC name of CH 2 — CH — C — CH 2 — CH 3 is:
|
|
Br
CONH 2
(a) 2-(Bromomethyl)-3-oxopentane carboxamide
(b) 1-Bromo-2-carbamoylpentan-3-one
(c) 5-Bromo-4-carbamoylpentan-3-one
(d) 2-(Bromomethyl)-3-oxopentanamide
45.
The IUPAC name of (CH 3 ) 3 C × CH 2 CH 2 Cl is:
(a) 2, 2-Dimethyl-4-chloro butane
(b) 1-Chloro-3, 3-dimethylbutane
(c) 4-Chloro-2, 2-dimethyl butane
(d) none of these
46.
The IUPAC name of CH 3 — CH — CH — CH — CHO is:
|
|
|
CH 3 OH OH
(a) 2, 3-Dihydroxy-4-methylpentanal
(b) 1-oxo-2, 3-Dihydroxy-4-methylpentane
(c) 2,3-Dihydroxy-4-methylpentanone
(d) 1, 2-Dihydroxy-3-methylbutanecarbaldehyde
47.
The IUPAC name of CH 3 — CO — CH — CH 2 — CH 2 Cl is:
|
CH 3
(a) 1-Chloro-3-methylpentan-4-one
(b) 1-Chloro-2-(oxoethylbutane)
(c) 5-Chloro-3-methylpentan-2-one
(d) 3-(2-Chloroethyl)butan-2-one
48.
OH
O
|
||
The IUPAC name of CH 3 — C — CH 2 — C — CH 3 is:
|
H
(a) 2-Hydroxypentan-4-one
(b) 4-Hydroxypentan-2-one
(c) 4-oxopentan-2-ol
(d) 2-oxopentan-4-ol
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49.
The IUPAC name of CH 3 — CH — CH — CH — CH 3 is:
|
|
|
OH
Br
Cl
(a) 3-Bromo-4-chloropentan-2-ol
(b) 3-Bromo-2-chloro-4-hydroxypentane
(c) 3-Bromo-2-chloropentane-4-ol
(d) none of these
50.
Br Cl
|
|
The IUPAC name of CH 3 — CH 2 — C — CH — CH 2 — Cl is:
|
OH
(a) 3-Bromo-4, 5-dichloropentan-3-ol
(b) 3-Bromo-1, 2-dichloro-3-hydroxypentane
(c) 3-Bromo-1, 2-dichloropentan-3-ol
(d) 3-Bromo-4, 5-dichloro-3-hydroxypentane
51.
52.
The IUPAC name of CH 3 — CH — CH 2 — O — C 2 H 5 is:
|
OH
(a) 1-Ethoxypropan-2-ol
(b) 3-Ethoxypropan-2-ol
(c) 1-Ethoxy-2-hydroxypropane
NH2
(d) none of these
The IUPAC name of
is:
Br
(a) 4-Bromo benzenamine
(b) 4-Amino-1-bromobenzene
(c) 4-Bromo benzenamide
(d) 1-Bromo benzencarboxamide
N
53.
The IUPAC name of
is:
(a) N, N-Dimethyl aminobenzene
(b) N, N-Dimethyl benzenamine
(c) (a) and (b) both are correct
(d) none of these
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613
OH
54.
The IUPAC name of
is:
O
(a) 2, 6-Dimethylhepta-2, 5-dienoic acid
(b) 3, 7-Dimethylhepta-2, 5-dienoic acid
(c) 1-Hydroxy-2, 6-dimethylhepta-2, 5-dienone
(d) none of these
55.
56.
The IUPAC name of
is:
CHO
(a) 3-Methylpent-1-en-4-al
(b) 3-Methylpent-4-enal
(c) 3-Methylpent-4-carbaldehyde
(d) 3-Methyl-5-oxopent-1-ene
O
The IUPAC name of
is:
(a) 2-Phenyl ethanone
(b) 1-Phenyl ethanone
(c) 1-(Oxoethyl)benzene
OH
(d) 1-(Ethyaloxo)-benzene
OH
57.
The IUPAC name of
is:
(a) 2-Hydroxybenzenol
(b) 1, 2-Dihydroxybenzene
(c) Benzene-1, 2-diol
(d) 2-Hydroxyphenol
OH O
58.
59.
The IUPAC name of
OH is:
(a) 2-Carboxyphenol
(b) 2-Hydroxybenzoic acid
(c) 1-Carboxy-2-hydroxybenzene
OH
(d) 2-Carboxy-1-hydroxybenzene
The IUPAC name of
is:
(a) 1,3-Dimethyl phenol
(b) 1-Hydroxy-2-6-dimethyl benzene
(c) 2, 6-Dimethyl benzenol
(d) 2-Hydroxy-1-3-dimethylbenzene
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614
60.
O
||
Ph ¾ CH == CH ¾ C ¾ OH
The IUPAC name is :
61.
62.
63.
64.
65.
66.
(a) 3-phenyl prop-2-enoic acid
(b) 3-phenol prop-1-enoic acid
(c) 3-carboxy-prop-1-ene benzene
(d) but-2-enoic acid
The IUPAC name of
Cl is:
(a) Chloromethylbenzene
(b) Chlorophenylmethane
(c) (a) and (b) both
(d) none of these
The IUPAC name of the compound having the formula is :
CH 3
|
H 3 C — C — CH == CH 2
|
CH 3
(a) 3, 3, 3-Trimethylprop-1-ene
(b) 1, 1, 1-Trimethylprop-2-ene
(c) 3, 3-Dimethylbut-1-ene
(d) 2, 2-Dimethylbut-3-ene
The IUPAC name of the compound CH 2 == CH — CH(CH 3 ) 2 is :
(a) 1, 1-Dimethylprop-2-ene
(b) 3-Methylbut-1-ene
(c) 2-Vinyl propane
(d) none of these
The number of sigma and pi-bonds in 1-butene 3-yne are :
(a) 5 sigma and 5 pi
(b) 7 sigma and 3 pi
(c) 8 sigma and 2 pi
(d) 6 sigma and 4 pi
The IUPAC name of C 6 H 5 COCl is :
(a) Benzoyl Chloride
(b) Benzene chloro ketone
(c) Benzene carbonyl chloride
(d) Chloro phenyl ketone
The IUPAC name of the following compound is :
OH
Br
CN
(a) 4-Bromo-3-cyanophenol
(b) 2-Bromo-5-hydroxybenzonitrile
(c) 2-Cyano-4-hydroxybromobenzene
(d) 6-Bromo-3-hydroxybenzonitrile
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615
67.
Many organic compounds contain more than one functional group. Which of the following is
both an aldehyde and an ether ?
O
O
O
O
O
O
H
O
(ii)
(i)
O
(iv)
(iii)
O
OCH3
O
68.
(v)
(a) (i) only
(b) (i) and (iv)
(c) (ii) and (v)
(d) (iii) and (iv)
What is the sum of positions assigned to bromine while numbering the Parent Chain in the
below compounds ?
Br
Br
Br
Br
(I)
(a) 13
69.
(II)
(b) 14
(III)
(IV)
(c) 15
(d) 16
How many number of compounds, which have same IUPAC name ?
OH
OH
OH
OH
OH
OH
OH
OH
(a) 0
(b) 1
(c) 2
(d) 3
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616
70.
How many total number of substituents are present in the following compound ?
Br
Cl
(a) 3
(b) 4
(c) 5
(d) 6
71.
Correct IUPAC name :
(a) 1-methyl-3-ethylcyclohexene
(b) 5-ethyl-1-methylcyclohexene
(c) 2-ethyl-4-methylcyclohexene
(d) 3-ethyl-1-methylcyclohexene
ANSWERS — LEVEL 1
1.
(c)
2.
(b)
3.
(b)
4.
(b)
9.
5.
(a)
6.
(a)
7.
(a)
8.
(a)
(d)
(b)
10.
(a)
11.
(c)
12.
(b)
13.
(a)
14.
(d)
15.
(c)
16.
17.
(a)
18.
(d)
19.
(a)
20.
(c)
21.
(d)
22.
(a)
23.
(b)
24.
(c)
25.
(b)
26.
(a)
27.
(d)
28.
(d)
29.
(a)
30.
(b)
31.
(a)
32.
(b)
33.
(c)
34.
(d)
35.
(a)
36.
(a)
37.
(b)
38.
(c)
39.
(d)
40.
(b)
41.
(a)
42.
(a)
43.
(a)
44.
(d)
45.
(b)
46.
(a)
47.
(c)
48.
(b)
49.
(a)
50.
(c)
51.
(a)
52.
(a)
53.
(b)
54.
(a)
55.
(b)
56.
(b)
57.
(c)
58.
(b)
59.
(c)
60.
(a)
61.
(b)
62.
(c)
63.
(b)
64.
(b)
65.
(c)
66.
(b)
67.
(b)
68.
(c)
69.
(a)
70.
(c)
71.
(b)
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617
Level - 2
Give the IUPAC name of the following compounds
Cl
OH
1.
OH
2.
OH
3.
Br
Cl
HO
Cl
4.
5.
OH
OH
Br
6.
Cl
Br
Br
Cl
HO
Br
7.
8.
Cl
Br
HO
OH
HO
10.
OH
9.
HO
OH
11.
Br
12.
Cl
OH
Br
Cl
13
OH
Cl
Cl
14.
15.
HO
Cl
HO
HO
16
OH
Br
OH
OH
17
18.
HO
OH
OH
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19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
OH
O
Cl
31.
32.
33.
Br
Br
O
O
O
O
34.
35.
O
36.
O
O
O
O
37.
O
O
38.
39.
O
O
O
40.
41.
O
42.
O
O
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619
O
43.
44.
O
45.
O
O
O
46.
47.
NH
Br
Br
Cl
50.
Cl
Br
52.
Br Cl
Cl 53.
O
Cl
Br
Cl
56.
Br
NH
54.
Cl
Br
Br
Br
Cl
O
NH
Br
O
57.
Br
O
Cl
NH
Cl
NH
Br
NH
O
58.
51.
NH
O
55.
O
O
O
NH
Cl
Br
NH
Br
NH
Br
O
N
O
48.
NH
O
49.
Cl
Cl
NH
Br
O
59.
60.
O
O
O
61.
62.
O
O
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620
Br
63.
O
O
Cl
OH
OH
O
O
O
65.
Br
O
64.
Br
NH
66.
OH
O
Cl
Br
OH
O
O
O
O
67.
68.
O
O
O
69.
Cl
70.
O
OH
O S O
71.
+O
O
O
72.
N
O
O
HO
O
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621
O
Br
Br
73.
74.
+O
-
N
75.
Br
Cl
O
76.
Cl
OH
O
OH
S
O
O
77.
Cl
Cl
O
OH
O
O
OH
O
O
O
78.
Cl
OH
OH
79.
80.
81.
O
Br
Cl
82.
HO
Br
Br
83.
Br
Cl
Cl
84.
Cl
O
O
HS
HO
Br
85.
O
O
Br
Cl
86.
87.
Cl
Br
O
O
Br
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622
O
O
O
88
O
89.
90.
O
Br
SH
Cl
O
O
O
O
Cl
91.
92.
93.
Br
Br
Br
O
O
O
94.
Cl
95.
96.
O
N+
Br
Cl
Br
O–
Cl
O
OHO
N+
97.
O
O–
CH3
98.
C — O — CH3
99.
O
C — NH 2
+
–O N
O
Br
100
O
O
C — O — CH3 101.
CH2 — CHO
O
102.
CO2H
C
H
O
103.
HO – CH2 – C – CH == CH – CH2 – CO2H
104.
CO2H
CH3
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623
Cl
O
CO2Et
105.
106. CH3 — NH — CHO
107.
Br
OH
Cl
O
OH
108.
109.
CN
C — NH — Ph 110.
Br
CONH2
CHO
111.
CHO
112.
Br
113.
CO2H
CO2H
OH
CO2H
114.
115.
Cl
CN
116.
O2N
NO2
CN
CO2H
CO2H
Cl
117.
118.
119.
C
O
NH2
O
OH
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624
Br
120.
121.
122.
Cl
123.
O
N+
O–
O–
O
N+
N+
O
O–
124.
O
N+
125.
O–
+
N
O–
O
O
N+
126.
O–
127.
128.
H2 N
O == S== O
OH
129.
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625
130. Give the IUPAC name of the following compounds :
CH 3
CH 3
|
|
(a) CH 3 - CH 2 - CH - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH - CH 3
CH 3
OH
|
|
(b) CH 3 - CH 2 - CH - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH - CH 3
CH3
(c) CH3 – CH2 – CH2– CH2 CH2 – CH3
|
|
CH3 – CH2 – CH – CH – CH3
(d)
CH3
CH3
CH3
CH3
(e)
CH3
CH3
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626
131. Give the IUPAC name of the following :
(a)
CH3
|
CH3
CH2—CH—CH3
|
|
CH3—CH—CH2—CH2—CH—CH2—CH2 —CH2—CH3
(b)
CH3
|2
1
CH3
CH2—CH—CH3
|
|
CH3—CH—CH2—CH2—CH—CH2 —CH2—CH3
(c)
CH3 CH3
|
|
CH3
CH2—CH—CH—CH3
|
|
CH3—CH2—CH—CH2—CH2—CH —CH2—CH2—CH2—CH2—CH3
1
2
3
4
5
6
7
8
9
3
8
7
1
6
2
5
3
4
4
5
6
7
8
9
10
11
OH
5
6
(d)
6
1
4 5
2
3
4
3
(e)
1
5
6
6
1
4
3
4 5
2
2
3
(f)
5
4
4
1
2
7
CH3
1
6
1
4
3
6
(g)
2 3
CH3
5
3
3 2
2
(h)
2
4
1
5
1
5
7
(i)
8
7
6
5
3
2
1
3
(j)
4
3
2
1
4
2
5
1
6
7
8
9
CH3
CH3 CH—CH3
CH3—CH—C—CH2—CH3
(k) CH3—CH2—CH2—CH2—CH—CH2 —CH2—CH2—CH3
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627
132. Match the Column :
Column (I)
Compound
Cl
Column (II)
IUPAC Name
(a)
(p)
1, 3-dibromo-2-chlorocyclopropane
(q)
1, 2-dibromo-3-chlorocyclopropene
(r)
3-bromo-1-chlorocyclopropene
(s)
1-bromo-3-chlorocyclopropene
Br
Br
(b)
Cl
Br
(c)
Cl
Br
Cl
(d)
Br
Br
133. Match the Column :
Column (I)
Cl
Column (II)
Cl
Br
(a)
(b)
(p) 1-butyl-4-methyl cyclohexane
(q) 2-bromo-1,1-dichloro cyclohexane
COOEt
(c)
(r) 1-Bromo-1,2-dichloro cyclohexane
CHO
Br
(d)
Cl
Cl
(s) Ethyl-2-formyl cyclohexane carboxylate
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Subjective Problems
1.
F
When IUPAC name of following compound is given, then double bond and substituent gets
respectively
( x and y) number so the sum of ( x + y) will be
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ANSWERS – IUPAC Name
1.
pent-4-yn-1-ol
2.
pent-4-en-1-ol
3.
(5E)-2-bromo-3-chlorohept-5-en-1-ol
4.
3-bromo-2-chloro-6-ethenylcyclohexanol
5.
4-bromo-3-chloro-5-cyclopropylcyclohexanol
6.
3-bromo-2-chloro-5-methylidenecyclohexanol
7.
3-bromo-2-chloro-5-methylidenecyclohexane-1,4-diol
8.
2-bromo-4-chloro-5-ethynylcyclohexanol
9.
cyclopenta-1,3-dien-1-ol
10. 2-bromo-5-chlorocyclopenta-2,4-dien-1-ol
11. cyclopenta-2,4-dien-1-ol
12. dodec-10-en-4-yne-3,8-diol
13. 1-chloro-3-methylbut-3-en-2-ol
14. 4-bromo-2-chlorooct-6-ene-3,5-diol
15. 3-chloro-5-(1-methylethenyl)cyclopenta-1,3-dien-1-ol
16. 2-bromo-5-chloro-3-methylidenecyclopentanol
17. cyclohexane-1,3,5-triol
18. cyclohexane-1,3-diol
19. cyclopenta-1,3-diene
20. (6E)-oct-6-en-1-yne
21. but-1-en-3-yne
22. (3Z)-pent-3-en-1-yne
23. buta-1,3-diyne
24. (2E)-dec-2-en-5-yne
25. (6Z)-dodec-6-en-2-yne
26. pent-1-en-4-yne
27. 4-ethynyl-1-methylcyclohexene
28. cyclooctyne
29. (2E)-hex-2-en-4-yne
30. 5-ethynylcyclopenta-1,3-diene
31. 5-(prop-2-enyl) cyclopenta-1,3-diene
32. 3,5-dibromo-2-chloro-4-ethenylcyclohexanol
33. cyclopropylmethyl cyclobutanecarboxylate
34. cyclobutylmethyl cyclopropanecarboxylate
35. ethyl ethanoate
36. 2-methylpropyl butanoate
37. prop-2-enyl 3-ethylpent-4-enoate
38. 4-methylpentan-2-one
39. 2,5-dimethylheptan-3-one
40. octa-1,7-dien-4-one
41. 3,4-dimethylheptane-2,6-dione
42. 9-ethyl-3-methylundecane-2,5,10-trione
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43. 5-methyloctanal
44. but-3-enal
45. 3-ethylheptanal
46. N,3-dibromobutanamide
47. 4-chloro-N-(3-chlorobutyl)butanamide
48. 3-bromo-N-(2-bromoethyl)-4-chloropentanamide
49. N,3-diethyl-N-propylpentanamide
50. 3-cyclopropyl-N-(3-cyclopropylbutyl)pentanamide
51. 4-bromo-N-(3-bromo-2-chloropropyl)-3-chloropentanamide
52. 3-bromo-4,5-dichloro-N-(2-chloroethyl)hexanamide
53. (5E)-N-(prop-2-en-yl)oct-5-enamide
54. 3-chloro-N-(2-cyclopentylpropyl)-4-cyclopropylpentanamide
55. 5,6-dibromo-3,4-dichloro-N-(2-chloroethyl)heptanamide
56. 3-bromo-N-(3-bromobutyl)butanamide
57. 3,4-dibromo-N-(3,4-dibromobutyl)pentanamide
58. 4-bromo-N-(3-chloro-2-cyclopropylpropyl)-3-(cyclopenta-2,4-dien-yl)butanamide
59. 2-oxopropanal
60. 4-oxopentanal
61. 3-oxobutanal
62. 3,4-dicyclopropyloct-7-yn-2-one
63. (2E,6E)-4-bromo-5-chloro-8-cyclopropyl-10-oxodeca-2,6-dienoic acid
64. 4,5,6,7,8,9-hexaethynyldodec-11-ynoic acid
65. (2E,6E)-5,9-dibromo-4-cyclopropyl-6-formylundeca-2,6-dienoic acid
66. 3-bromo-5-chloro-6-(formylamino)hexanoic acid
67. ethyl 3-phenylpropanoate
68. ethyl methyl benzene-1,3-dicarboxylate
69. ethenylbenzene
70. benzoyl chloride
71. methyl 4-acetyl-2-nitrobenzoate
72. 2-formyl-4-sulphobenzoic acid
73. 1,2-dibromo-4-chlorobenzene
74. octylbenzene
75. 2-bromo-1-chloro-4-nitrobenzene
76. 4-formyl-2-sulphobenzoic acid
77. 3-(trichloromethyl)benzoic acid
78. 4-(ethoxycarbonyl)benzoic acid
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79. 4-ethenylbenzoic acid
80. 4-benzylbenzoic acid
81. biphenyl
82. 1,2,5-tribromo-3,4,6-trichlorobenzene
83. ethyl 4-acetylbenzoate
84. 2-bromo-6-chlorophenol
85. 2, 4, 6-tribromophenol
86. ethyl 4-bromo-3-chlorobenzoate
87. ethyl 3-chloro-4-mercapto/sulpho benzoate
88. ethyl 4-(chlorocarbonyl)benzoate
89. 3-bromo-4-sulphobenzaldehyde
90. benzene-1, 3-dicarbaldehyde
91. 4-bromo-2-chlorobenzaldehyde
92. 1-phenylpentan-1-one
93. 1-(3-bromophenyl)hexan-1-one
94. 4-bromo-1-(3-bromo-4-chlorophenyl)pentan-1-one
95. 1-(3-bromo-5-chlorophenyl)-2-chloroethanone
96. 1-(3-nitrophenyl)ethanone
97. 2,4-dinitrobenzoic acid
98. methylcyclohexane carboxylate
99. 2-methylcyclopentane carboxamide
100. methyl-2-bromocyclohexane carboxylate 101. 2-(2-methylcyclobut-1-enyl)ethanal
102. 4-formyl-2-oxocyclohexane-1-carboxylic acid
103. 5-cyclohexyl-6-hydroxy-5-methylhex-3-en-1-oic acid
104. 2-oxocyclohexane-1-carboxylic acid
105. ethyl-2-oxocyclohexane-1-carboxylate
106. N-methylmethanamide
107. 2-bromo-4-chloro-5-ethynylcyclohexanol
108. 2-bromo-6-chloro-3-methylidene-cyclohexanol
109. N-phenylcyclohexane carboxamide
110. cyclohexane carbonitrile
111. cyclopentanecarbaldehyde
112. cyclohexanecarboxamide
113. 2-bromo-6-methyl-cyclohexanecarbaldehyde
114. cyclopropane carboxylic acid
115. 4-cyno-2-hydroxy-5-nitrocyclohexane carboxylic acid
116. 6-chloro-5-cyno-4-nitrocyclohex-2-ene carboxylic acid
117. 6-chloro-4-(3-oxo cyclobutyl)cyclohex-2-ene carboxylic acid
118. 4-(2-amino-4-hydroxycyclopentyl cyclohex-2-enecarboxylic acid
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119. cyclohexylidenemethanone
120. 2-bromo-4-chloro-1-methylbenzene
121. 1,2-diethyl-3-methyl-4-propylbenzene
122. 1-ethyl-3-nitrobenzene
123. 2-methyl-1, 3, 5-trinitrobenzene
124. 1-methyl-3-nitrobenzene
125. Diphenylmethane
126. 4-Methyl-3-nitrobenzene sulphonic acid
127. 1-ethenyl-4-methylbenzene
128. heptan-3-amine
129. 2-methylpentan-3-amine
130. (a) 2,11-dimethyltridecane
(b) 12-methyl-tridecan-3-ol
(c) 4-ethyl-3-methyloctane
(d) 1,2,7-trimethylcyclopentadecane
(e) 1,1,2,5-tetramethylcyclopentane
131. (a) 5-isobutyl-2-methylnonane,
5-2-methylnonane (2-methylpropyl)
(b) 2,7-dimethyl-4-propyloctane
(c) 6-(2,3-dimethylbutyl) 3-methyl undecane
(d) 1,1,2,6-tetramethylcyclohexane
(e) 2,2,3-trimethylcyclohexanol
(f) 1,2,4-trimethylcyclopentane
(g) 2-methylbicyclo[3.1.1] heptane
(h) 2-methylbicyclo[3.1.1] heptane
(i) 2,2,6,6,7-pentamethyloctane
(j) 4-(1methylpropyl)-2,3,5-trimethyl nonane Not 2-butyl
(k) 5-(1-ethyl-2-methyl-1-(1-methylethyl)propyl) nonane
132.
a - r; b - s; c - q; d - p
133. a - q; b - p; c - s; d - r
Subjective Problems
1. 4
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