ORGANIC CHEMISTRY
Race
No.
TOPIC NAME CONTENTS
Page
No.
01
IUPAC SYSTEM
1
02
STRUCTURAL ISOMERISM
3
03
GEOMETRICAL ISOMERISM
5
04
OPTICAL ISOMERISM
7
05
ISOMERISM (COMPLETE)
9
06
ELECTRONIC DISPLACEMENT
11
07
REACTION MECHANISM ( PART-II )
15
08
REACTION MECHANISM ( PART-II )
17
09
REACTION MECHANISM ( PART-II )
21
10
HYDROCARBON
23
11
HALOGEN, OXYGEN & NITROGEN
25
CONTAINING COMPOUNDS
12
BASED ON CONVERSIONS
28
13
NCERT CONVERSIONS
31
14
NCERT CONVERSIONS
33
TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
IUPAC SYSTEM
RACE # 01
Write down the IUPAC names of the following
compounds :-
Cl
OH
12.
CH3
1.
CH3–CH–CH–CH–CH3
C2H5
OH
13.
CH2=CH–CH–CH2–CN
CH2–OH
–
2.
3.
OH OH
CH2CH2CH3
CH3–CH–CH2–CH2–CH–CH–CH3
CH2Cl
14.
Br
Cl
Cl
O
4.
CH2CH3
CH3–C–C(CH3)3
15.
OH
OH
CH3
CH3–CH–CH2–C–O–C2H5
NC
O
O
––
–
5.
OH
16.
O O
6.
–
–
CN
CH3–CH–CH–CH 2–CH3
CN
17.
7.
CH2=CH–CH–CH2–CHO
O
C C–CH3
CONH2
Cl
8.
Br
Cl
9.
18.
Br
Cl–C–CH2–CH
19.
CH2
10.
Cl
CH3–CH2–C–CH2–OH
Br
Br
CH2=CH–CH–C CH
CH3
11.
H
C
CH
CH
CH=CH2
E
CH3 CH3
CH2
O
20.
CH2CH3
Your Target is to secure Good Rank in Pre-Medical 2021
1
TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
Br
Cl
Br
Br
Cl
25.
21.
Me
Me
Et
Cl
26.
22.
CH3
CH3
N–CHO
27.
O
C
23.
C
28.
O
O
CN
29.
24.
CH2CH3
30.
ANSWER KEY
1.
3,4-Dimethylhexan-2-ol
16.
3-Formyl-4-methyl-5-oxo pentanoic acid
2.
3-(Hydroxymethyl) pent-4-ene-1-nitrile
17.
2, 3-Epoxypentane
3.
1-Chloro-5-(1'-chloroethyl)-2-methyloctane
18.
Cyclopentanecarboxamide
4.
2, 2, 3, 3-Tetramethylpentane
19.
1,3-Dibromo-2-chloro cycloprop-1-ene
5.
Ethyl-3-isocyanobutanoate
20.
2-Ethyl-1, 1-dimethylcyclopropane
6.
2-Ethyl-3-methylbutanedinitrile
21.
1, 2, 4-Tribromo-3, 5, 6-trichlorocyclohexane
7.
3-Ethenyl hex-4-yn-1-al
22.
N, N-Dimethylmethanamide
8.
3,3-Dibromo-1,1,1-trichloropropane
23.
Cyclohexane-1, 2-dicarboxylicanhydride
9.
2-Ethylprop-2-en-1-ol
24.
3-Ethylcyclohexanecarbonitrile
10.
3-Methylpent-1-en-4-yne
25.
1-Ethyl-6,6-dimethyl-1-cyclohexene
11.
2-Ethenylbut-3-enal
26.
Hex–4–en–1–yne
12.
1-Chloro-3-methylbut-3-en-2-ol
27.
4-Methylhept-5-en-2-ol
13.
5-Methyl hex-2-yne
28.
Ethyl-4-cyanobutanoate
14.
4-Bromo-2-chloro oct-6-en-3,5-diol
29.
2-Chlorobutanoylchloride
15.
2-Hydroxybutanoic acid
30.
2-Ethyl-4-oxobutanenitrile
2
Your Target is to secure Good Rank in Pre-Medical 2021
E
TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
STRUCTURAL ISOMERISM
1.
RACE # 02
Isomerism shown by the following compounds
5.
O
–C–O–
(1) 2
C=C
H
H
Cl
6.
(3) 4
(4) 6
How many amines are possible with the molecular
formula C4H11N (structural isomers only) :(1) 6
(2) 7
(3) 8
(4) 9
is :-
–C–O–
7.
C=C
H
H
(2) 3
&
O
Cl
Number of structural isomers possible for
dibromoderivative of an alkene with molar
mass 186 gm mol–1 is (atomic mass of Br = 80)
How many benzenoid isomers are possible for
M.F. C7H8O :(1) 3
(2) 4
(3) 5
(4) 6
(1) Functional group isomerism
(2) Geometrical isomerism
8.
(3) Metamerism
(4) Position isomerism
How many total structural isomers of 3° amines
are possible with the molecular formula
C 6 H 15 N
(1) 4
2.
How many structural isomers are possible when
one H-atom of anthracene is replaced by
chlorine :(1) 3
(2) 7
Br
(3) 4
(4) 6
3.
and
are :Br
Br
(1) Chain isomers
Me
OH
Only two isomeric monochloro derivatives are
possible for (excluding stereo) :(1) n-Butane
(2) 2,2-Dimethylpentane
(3) Benzene
(4) Neopentane
Me
How many alkenes (only structural isomers)
are possible with the molecular formula C4H8
(1) 4
(2) 3
(3) 5
Me
(4) 6
Which of the following is correct :(1)
O
O
,
H
Functional group isomers
Me
Me
O–Me
11.
(2)
OH
;
Position isomers
O–Et
O
O
(I)
(4) 5
(2) Geometrical isomers
Which of the following is not the correct
relationship :
Me
10.
COOH
(3) Functional isomers(4) Position isomers
4.
(3) 6
COOH Br
COOH
HOOC
9.
(2) 7
(II)
(III)
(1) I and IV are positional isomers
(2) I and II are functional isomers
(3) I and III are chain isomers
(IV)
(3)
;
NH2 H2N
H
Position and functional group isomers
(4) All of these
(4) II & IV are metamers
E
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TARGET : PRE-MEDICAL 2021
12.
Minimum C-atom required for aliphatic
2° amine to show chain isomerism are :(1) 4
(2) 6
(3) 3
(4) 5
ORGANIC CHEMISTRY
iii. CH3CH2CH2CHCH3 and CH3CH2CHCH2CH3
COOH
COOH
O
13.
Isomerism shown by
O
–S–O–
–Me & Me–
O
(1)
(2)
(3)
(4)
14.
15.
16.
O
iv.
O
O
and
O
–S–O–
O
17.
Chain isomerism
Positional isomerism
Metamerism
Functional group isomerism
What is relation between following compounds
CH3 CH2 CH CH2 CHO & CH3 CH CH2 CH2 CHO
CN
CN
Branched chain isomer of a hydrocarbon
having molecular mass 72u gives only one
isomeric alkyl halide after monosubstitution.
The hydrocarbon is :(1) neohexane
(2) t-butyl chloride
(3) neopentane
(4) isooctane
How many structural isomers are possible of
C5H12O :(1) 5
(2) 8
(3) 13
(4) 14
18.
(1) positional isomers (2) chain isomers
(3) optical isomers
(4) metamers
No. of structural isomeric alkenes (molecular
formula=C 6 H12 ) which all give n-hexane on
hydrogenation in presence of metal catalyst
19.
(1) 2
(2) 3
(3) 4
(4) 5
How many isomeric geminal dihalides are
possible for the compound having M.F. C3H6Cl2
20.
(1) 1
(2) 2
(3) 3
(4) 4
Which is the metamer of the compound P ?
Find out relation between the following
compounds:
COOH
O
O
i.
and
CH3
(1)
O
O
Cl
ii.
OH
(2) H C
3
OH
CH 2CH 3
C–Cl
CH2CH3
and
OH
(3)
(4)
ANSWER KEY
4
Que.
1
2
3
4
5
6
7
8
9
10
Ans
3
1
4
1
1
3
3
2
1
2
Que.
11
12
13
14
15
16
Ans
2
4
3
3
4
(i) F.G.I. (ii) F.G.I. (iii) C.I. (iv) F.G.I.
Que.
Ans
17
2
18
2
19
2
20
4
Your Target is to secure Good Rank in Pre-Medical 2021
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TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
GEOMETRICAL ISOMERISM
1.
2.
3.
Which of the following compound have
minimum dipole moment :
(1) CH3 –CH2 –C CH
(2) CH3–C C–CH3
(3) CH3–CH=CH2
(4) CH3–C CH
The compound CH3–C–Cl is :I–C–Br
7.
(1) trans
(2) cis
(3) Z
(4) E
How many geometrical isomers are possible for
the given compound
Br
Cl
(1)
CH3
C=C
H
(2)
Cl
CH 3
C=C
Br
H
(3)
Cl
CH3
C=C
Br
H
(4)
H
CH3
C=C
CH3
H
(1) 2
8.
C=C
CCl3
H
(1)
(2)
(3)
(4)
C=C
CCl3
H
Boiling
point
I > II
II > I
I > II
II > I
Melting
point
II > I
II > I
I > II
I > II
H
Stability
I > II
II > I
I > II
I > II
In which compound cis-trans nomenclature
cannot be used :
(1) CH3–CH=CH–COOH
(2) C6H5–CH=CH–C6H5
(3) C6H5–CH=CHD
(4) C6H5–CH=C
CH3
Cl
Cl
(1) 0
9.
E
CN
(2) E, E
(4) Z,Z
Cl
(2) 1
(3) 2
(4) 3
Which of the following compounds can show
geometrical isomerism :
(i)
Pent-3-en-1-yne
(ii) Acetaldoxime
(iii) Pent-1-ene
(iv) 1-chloropropene
(v) 2-Methylbut-2-ene
(vi) But-2-yne
(vii) 2-chlorobutane
(viii) Butenyne
(ix) CH3 – CH = CH – CH3
Cl
(x)
Cl
C
C
H
H
H
COOH
COOH
(xi)
COOH
CH2OH
(1) E
(3) E,Z
(4) 8
How many geometrical isomers are possible for
H
Assign configuration to the following
CN
H 2N–H 2C
(3) 6
CCl3
(II)
(I)
Dipole
moment
I > II
II > I
I > II
II > I
(2) 4
Cl
Which is true for the following isomeric forms
I & II respectively :
H
5.
6.
Which one of the following is a Z isomer ?
CCl3
4.
RACE # 03
(xii)
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TARGET : PRE-MEDICAL 2021
10.
Assign the configuration E/Z to the following
compounds.
11.
Which of the following compounds have zero
dipole moment.
(i)
CCl4
CH3
H2N
C
(i)
(ii)
CH3
H
C
Cl
NO2
(iii)
OCH3
H2N
ORGANIC CHEMISTRY
H
C2H5
C=C
Cl
C=C
H
H
Cl
C
(ii)
(iv) Cl
C
HS-CH2
Cl
F
12.
C
(iii)
Compare dipole moment of the following
C
H
(a) (i)
D
14
C
14
MeO
13.
CH3
CH3
C 2 H5
H3C
HC CH2
H3C
C
14.
CH2-Cl
C
I
C
D3C CH2
CH2–CH3
15.
F
Br
Cl
C
(vii)
C
H
C=C
(ii)
CH3
H
Cl
F
(ii)
C=C
Cl
H
C=C
H
(2)
(3) HO–N=N–OH
(4) (CH3)2 C=NOH
According to CIP sequence rules the correct
order of priority for the given groups is
(1) –COOH > –CH2OH > –OH > –CHO
(2) –COOH > –CHO > –CH2OH> –OH
(3) –OH > –CH2OH > –CHO> –COOH
(4) –OH > –COOH > –CHO> –CH2 OH
GI is shown by :
CH(CH3)2
F
(vi)
Cl
(1) CH3 CH=NOH
C
H2C CH
H
C=C
H
CH3
H
(c) (i) CH3–CH2–C CH (ii) CH3–C C–CH3
Which will not show G.I. ?
C
(iv)
Cl
F
(b) (i)
H
CH3
H3C
(v)
Cl
F
(1)
Cl
(2) CH3CH=C=CHCH3
OHC
C
(viii)
CH2–OH
(3)
C
NC
C–OH
(4) CH 3CH=C=C=CH2
O
ANSWER KEY
Que.
1
Ans
2
2
3
1
4
10
Que.
Ans Z-i,ii, iii,- E- iv, v, vi, vii, viii
6
4
5
6
4
2
4
11
i & iii, iv
7
9
8
1
3
12
(a) i > ii (b) i < ii (c) i > ii
Your Target is to secure Good Rank in Pre-Medical 2021
i, ii, iv, ix, x, xi, xii
13
4
14
4
15
1
E
TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
OPTICAL ISOMERISM
1.
RACE # 04
Match Column - I with Column - II and select
the correct answer using the codes given below:
Column - I
(A) Meso
4.
Column - I
Column - II
(A) Constitutional
(P) An equimolar
compound
Match Column - I with Column - II and select
the correct answer using the codes given below :
mixture of
Column - II
(P) Stereoisomers that
are not mirror
image isomer
enantiomers
(B) Enantiomers
(B) Stereoisomers
(Q) Stereoisomers that
(Q) Isomers that have
are not mirror
same constitution
images
but differ in the
(C) Diastereomers
(R) Non superimposable
mirror image
(D) Racemates
(Racemic
mixture)
(S) An optically inactive
compound whose
molecule is achiral
arrangement of their
atoms in space
(C) Enantiomers
(R) Isomers that differ
in the order in which
their atoms are
even though they
connected
contain chiral
(D) Diastereoisomers (S) Stereoisomers that
centres
2.
(1) A-S, B-R, C-Q, D-P
object and its non
(2) A-S, B-R, C-P, D-Q
superimposable
(3) A-R, B-S, C-Q, D-P
mirror image
(4) A-R, B-S, C-P, D-Q
(1) A-P, B-Q, C-S, D-R
The correct absolute configuration assigned for
compound (I) and (II) respectively is :
(2) A-P, B-Q, C-R, D-S
COOH
(I) H—–—NH2
(1) R, R
5.
CH 2SH
(2) R, S
(3) S, S
(1)
CH3
(4) S, R
H
OH
OH
(3)
CH3
CH3
H
H
H
(4)
H
6.
H
HO
OH
CH3
H
Cl
(II) Br—–—CH3
Br
H
(1) enantiomers
(2) diastereomers
(3) meso compounds (4) homomers
H
(2)
The following structures respresent a pair of:
(I) H—–—Cl
Which of the following cyclopentane
derivative is optically inactive ?
OH
E
(3) A-R, B-Q, C-S, D-P
(4) A-R, B-Q, C-P, D-S
COOH
(II) H—–—NH2
CH3
3.
are related as an
CH3
H—–—OH
Br—–—H
C2H5
H
HO—–—CH3
H—–—C2H5
Br
The molecules represented by the above two
structures are :
(1) identical
(2) enantiomers
(3) diastereomers
(4) epimers
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TARGET : PRE-MEDICAL 2021
7.
How many chiral centres are present in the
following compound :-
11.
ORGANIC CHEMISTRY
Which has R-configuration
H
O
(1) CH3CH2
Br
O
CH=CH2
Cl
Me
(1) 4
8.
CH=CH2
(2) 5
(3) 6
(1)
(3)
CH2CH3
H
H
Cl
CH3
(2)
CH3
H
H
CH3
(4)
H
CH2CH3
(4) CH2=CH
Cl
H
CH3
Cl
12.
In which of the following compound have
plane of symmetry ?
CH3
H
H
Cl
CH3
are :C2H5
Br
(3)
(4)
Cl
13.
C
I
H
Cl
Which of the following compound will not
show optical isomerism
CH3
CH3
COOH
Br
CN
OH
Cl
CH3
Cl
Configurations of the two centres in the
following molecule are :
(1) (2R, 3S)
(3) (2S, 3S)
Cl
(2)
CH3
Identical
Enantiomers
Diastereomers
Positional isomers
H
H
CH3
(1)
Cl
C2H5
H
Br
CH3
HS
SH
& H
H
CH=CH2
CH 3
CH 3
Cl
CH3
(1)
(2)
(3)
(4)
(3) Br
H
H
Cl
Cl
H
CH2CH3
Cl
Cl
10.
H
Which of the following structure does not
represent meso isomer :CH3
9
(2) Br
(4) 7
(1)
(2)
CH3
CH3
CH3
(2) (2R, 3R)
(4) (2S, 3R)
(3)
(4) all of these
CH3
ANSWER KEY
Que.
1
2
3
4
5
6
7
8
9
10
11
12
13
Ans
1
2
3
3
4
1
3
1
1
1
1
1
2
8
Your Target is to secure Good Rank in Pre-Medical 2021
E
TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
ISOMERISM (COMPLETE)
1.
RACE # 05
Which of the following is optically active :-
5.
Which of the following statements is true :-
(1) 1,1–Dibromo-1-chloro propane
(1) Racemic mixture is a resolvable mixture
(2) 1,3-Dibromo-1-chloropropane
(2) Meso isomer is optically inactive due to
internal compensation
(3) 1,1-Dibromo-3-chloro propane
(4) 1,3-Dibromo-2-chloropropane
2.
(3) Racemic mixture is optically inactive due
to external compensation
Which is the highest energy conformation of
butane :-
(4) All
6.
Me
(1)
unsymmetrical compound having 'n' no. of
Me
H
chiral C-atoms :-
(2)
(1) 2n–1
H
H
H
7.
Me
H
(3) 2n/2
(4) 2(n–1)/2
O–CH 2–CH3
CH3
;
O–CH3
C2H5
Metamers
(4)
H
Me
H
(2)
3.
(2) 2n
Which of the following is incorrectly matched:-
(1)
H
(3)
How many racemic mixture are possible for an
O–H
CH3
Which conformer of the given compound is
most stable (rotation about C–C bond) :-
CH2OH
;
Functional group isomers
CH3
HO–CH 2 –CH 2 –NO 2
(3)
(1) Staggered
;
Chain isomers
(2) Gauche
(3) Fully eclipsed
(4) CH3–CH2
;
CH2–CH3
Metamers
(4) Partially eclipsed
4.
(1) Compound having chiral–C essentially
shows optical isomerism
(2) Compound having one chiral–C can not
have meso isomer
(3) Chiral molecule may or may not have
chiral–C
CH2–CH2–CH3
CH3
Which of the following statement is true :8.
Sum of X, Y and Z is :(a) C4 H8 O
No. of aldehydes = X
(b) C5 H12
No. of chain isomers=Y
(c) C4H 8
Maximum no. of alkenes=Z
(1) 10
(2) 7
(3) 9
(4) 8
(4) All
E
Your Target is to secure Good Rank in Pre-Medical 2021
9
TARGET : PRE-MEDICAL 2021
9.
Which of the following is false for the given
molecules :CHO
H
OH
OH H
CHO
CHO HO
CH3
C
11.
(4) All of these
13.
Number of stereoisomers of the given
compound is
CH3 CH CH CH CH3
OH
14.
(1) 2
(2) 3
(3) 4
(4) 6
Which of the following can show both
tautomerism and optical isomerism
O
OH
(1)
C
C
Me
O
(3)
CH3
Cl
15.
Cl
Cl
H
(2)
CH3
CH3
Cl
(3)
(4)
(3)
Cl
Cl
Cl
(2)
(2)
(III)
Which of the following compounds can show
geometrical isomerism :(1)
(1)
H
(II)
(1) Equimolecular mixture of I and II does not
show optical activity
(2) II and III have different behaviour towards
PPL
(3) II & III are identical
(4) I & II can not be separated by fractional
distillation method from their mixture.
10.
Which one of following isomer is meso :-
CH3
CH3
(I)
12.
ORGANIC CHEMISTRY
O
(4)
O
Which of the following compound can not
show tautomerism ?
(1)
C
H
Which of following compound is chiral
(2) CH 2=CH–OH
CH3
Cl
Cl
H
(2) H
(1)
(3)
CH3
CH3
Cl
(3)
(4)
(4)
Cl
Cl
CH3
ANSWER KEY
Que.
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
Ans
2
1
2
4
4
1
4
3
3
2
1
1
3
2
4
10
Your Target is to secure Good Rank in Pre-Medical 2021
E
TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
ELECTRONIC DISPLACEMENT
RACE # 06
Reconcile the concept :
Carbocation i.e. carbon bearing positive charge.
Carbocation are stabilized by +I effect and destabilized by –I effect.
As +I effect tends to disperse the +ve charge, more the dispersion of +ve charge more will be stabilization
of carbocation.
–I effect tends to intensify the charge on C (carbocation), more the intensification of charge more
will be destabilization of carbocation.
Carbanion i.e. carbon bearing –ve charge.
–I effect tends to disperse the –ve charge thus stabilized the carbanion.
+I effect tends to intensify the –ve charge thus destabilized the carbanion.
O R2
–I effect :
> – OH > – C
+ I effect:
1.
2.
3.
4.
N R3
N H3 > – NO2 > – CN > – COOH > Halogens > – OR
CH > – NH2 > – Ph > CH2 = CH –
O > (CH3)3 C – > (CH3)2CH– > CH3 – CH2 – > – CD3 > – CH3 > – D > – H
NH
The order of the –I effect orbitals in :
(1) sp3 > sp2 > sp
(2) sp2 > sp3 > sp
(3) sp > sp2 > sp3
(4) sp 3 > sp > sp2
The number of electron present in the valence
shell of carbon of carbanion bearing –ve charge
(1) 8
(2) 7
(3) 6
(4) 4
Arrange the following in the stability order :
(I) CH3 –C C
(II) CH3 –CH=CH
(III) CH3 –CH–CH3
(IV) CH3 –CH2–CH2
Arrange given carbocations in decreasing order
of their stability:
F
(i)
,
F
(I)
Arrange given compounds in decreasing order
of their Ka value:
(i) HCOOH ; CH3 COOH ; C 2H5COOH ;
(II)
(III)
C3 H7 –COOH
(III)
(IV)
Cl
(ii)
COOH
COOH
CH3
E
6.
(I)
;
(II)
;
;
(I)
(II)
;
(I)
;
CH2
CH3
(ii)
Arrange given anions in decreasing order of
their stability
,
CH2
CH2
5.
CH3
(III)
Cl
(II)
COOH
Cl
(III)
Your Target is to secure Good Rank in Pre-Medical 2021
11
TARGET : PRE-MEDICAL 2021
11.
HOOC
COOH ; HOOC
(iii)
(I)
Identify more stable canonical structure :
O2 N
(1)
H
C
F
(II)
7.
8.
9.
10.
(A)
(C)
(B)
CH2
C
(4) CH3
12.
N
••
O
(D)
CH3
C
O
Acetic acid is considered as resonance hybrid
O
O
O
CH3–C–O–H
(I)
CH3–C=O–H
(II)
CH3–C–O
–H
••
(III)
13.
••
NH2
NH3
(1)
14.
O
••
CH3–C–O–H
(IV)
Which of the following order is correct for the
stability of four contributing structure :
(1) I > II > III > IV
(2) I > II > IV > III
(3) I > III > II > IV
(4) I > IV > III > II
In which of the following molecule group present
on ring is not involved in resonance :
(2)
Cl
OH
(3)
(4)
In each of the following pairs of ions which ion
is more stable :
(i)
(I) C6H5 – CH2 and (II) CH2
(ii)
(I) CH3 – CH2 and (II) CH2
(iii)
(I)
(iv)
(I) CH –C–CH
3
3
CH – CH 2
CH
••
N
H
N
••
OH
CH2=C=CH
CH2
COOH
Which among the given acid has lowest pKa value
(1) Chloroacetic acid
(2) Bromoacetic acid
(3) Nitroacetic acid
(4) Cyanoacetic acid
Arrange the compounds in order of decreasing
acidity :
(I) ClCH2 – CH2 – OH
(II) Cl2CH – CH2 – OH
(III) Cl – CH2 – CH2 – CH2 – OH
(IV) CH 3 – CH2 – CH2 – OH
(1) I > II > III > IV
(2) IV > III > II > I
(3) II > I > IV > III
(4) II > I > III > IV
Consider the given compounds :
(1) CH3 – CH2 – NH2 (2) CH 3 – CH = NH
(3) CH 3 – C N
(4) C2H5 – NH – C2H5
Arrange basicity of these compounds in
decreasing order :
(1) 4 > 1 > 2 > 3
(2) 1 > 2 > 3 > 4
(3) 1 > 4 > 2 > 3
(4) 4 > 1 > 3 > 2
In which of the following cases lone-pair is
involved in resonance :
C
(3)
COOH
HOOC
(III)
H
OH
(2) CH2–C CH
COOH ;
(I)
O
O
COOH
(II)
HOOC –COOH
(III)
(iv)
ORGANIC CHEMISTRY
CH2
CH2
and (II)
••
N
H
CH3–CH–CH3
••
(E) CH2=CH–CH=NH
and (II)
CH3–N–CH3
CH3–C–CH3
••
(F) CH2=CH–O–CH=CH
2
••
15.
(G) CH2=CH–C N:
CH2
(H)
12
••
O
••
Among the following compounds, the strongest
base is :
O
(I)
••
O
••
NH
(1) NH2–C–NH2
(2) NH2–C–NH2
(3) C6H5–NH2
(4) CH3–NH–CH3
Your Target is to secure Good Rank in Pre-Medical 2021
E
TARGET : PRE-MEDICAL 2021
16.
The correct order of decreasing basic strengths of
x, y and z is :
(x)
(z)
(y)
NH
21.
N–H
N
(2)
(1) x > y > z
(2) x > z > y
(3) y > x > z
(4) y > z > x
Consider the following compounds :
;
(1)
(2)
NH2
(4)
;
NO2
22.
Compare C–C bond rotation in the following
molecules :-
NH2
;
(4)
CHO
18.
(3)
NH2
NH2
(3)
Which of the following is non-aromatic :
(1)
O
17.
ORGANIC CHEMISTRY
CH3
(1)
(2)
(3)
(4)
(II)
(I)
Arrange these compounds in decreasing order
of their basicity :
(1) 1 > 2 > 3 > 4
(2) 2 > 3 > 1 > 4
(3) 4 > 1 > 3 > 2
(4) 4 > 1 > 2 > 3
Which shows aromatic character :
23.
(1) I > II
(2) II > I
(3) I = II
(4) can not be compared
What is the order of indicated bond length for
the following set of molecules :
O
19.
(a)
Among the following the aromatic compound is
(1)
(2)
(3)
(4)
O
(I)
(II)
OH
O
NH2
NH2
20.
Which of the following is anti-aromatic
species :
(b) (I)
N
(II)
CHO
(2)
(1)
:
S
NH2
(III)
(3)
E
(C–O bond)
(IV)
(III)
(IV) CH2=NH (C–N bond)
(4)
Your Target is to secure Good Rank in Pre-Medical 2021
13
TARGET : PRE-MEDICAL 2021
24.
Product (A) will be :HOOC
ORGANIC CHEMISTRY
HOOC
OH
OH
2Moles NaNH2
O2N
(4)
A
O2N
CH
C
COOH
COO
HOOC
25.
O
Which of the following represents the correct
order of stability of the given carbocations ?
(1)
CH2
O2N
CH
COO
I
OOC
(1) III > I > II
(3) III > II > I
OH
(2)
26.
O2N
III
(2) I > III > II
(4) II > III > I
Which of the following group has maximum
hyperconjugation effect but minimum inductive
effect
(1) –CH3
(2) –CH2–CH3
(3) –CD3
C
COOH
OOC
OH
(3)
II
(4)
O2N
CH3
C CH3
CH3
CH
COO
ANSWER KEY
Que.
1
2
3
Ans
3
1
I > II > IV > III
5
4
(i) I > II > IV > III
(i) III > II > I (ii) I > II > III
Que.
6
7
8
9
Ans
(i) I > II > III > IV (ii) I > II > III (iii) III > II > I (iv) I > III > II
3
4
1
Que.
10
11
12
13
Ans
B,D,F,I
(1) I > II (2) II > I (3) I > II (4) II > I
1
2
Que.
14
15
16
17
18
19
Ans
(i) I > II (ii) I > II (iii) II > I (iv) II > I
2
2
3
2
1
Que.
20
21
22
23
24
25
26
Ans
4
2
1
(a) IV > I > II > III (b) III > II > I > IV
3
1
1
14
Your Target is to secure Good Rank in Pre-Medical 2021
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TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
REACTION MECHANISM ( PART-II )
1.
Reactivity order of the following compounds
for hydrochlorination (HCl) is
CH2 = CH – Cl
RACE # 07
6.
(CH3)2C = CH2
(I)
(II)
CH2 = CH – CHO
(III)
2.
(1) I > II > III
(2) II > III > I
(3) II > I > III
(4) III > I > II
Arrange the following compounds in
decreasing order of reactivity for EAR :-
Ph–C=CH–CH 3 (II)
CH 3
Ph–CH=CH2 (I)
Ph2C=CH–CH3 (III)
(1) IV > I > II > III
(3) II > III > I > IV
3.
CH3–CH=CH
OH
H Br
A
9.
OH
(2) CH3CH2CH(Br)
OH
(3) CH3CH2CH(Br)
Br
(4) CH3CH(Br)CH2
Br
Br2
NaCl
(c) H3C
10.
?
(3)
Cl
Br
(1) HCHO;
Br
(4) Both 1 and 2
(3)
5.
CH2=CH–CCl3
HBr
(1) CH2 =CH–CBr3
?
(2) CH2–CH 2–CCl3
(4)
Br
(3) CH3–CH–CCl3
Br
E
(4) CH2–CH–CCl3
Br
Br
C–CH3
O
O
C–CH3 (d) O2N
C–CH3
H
H
CH3
C
OH
CN
H
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C
OH
;
H
H
CH3
C
OH
COOH
OH
C
;
CN
H
COOH
C2H5
OH
C
CH3CH2CHO;
;
H
COOH
C2H5
OH
C
H
CN
CH3
CH3
OH
C O ;
C
;
CH3
CH3
CN
CH3
OH
C
CH3
COOH
(2) CH3CHO;
Cl
(b) Cl
(1) a > b > c > d
(2) c > a > b > d
(3) d > b > a > c
(4) d > a > b > c
A carbonyl compound 'A' reacts with hydrogen
cyanide to form a cyanohydrin 'B' which on
hydrolysis gives an optically active alpha
hydroxy acid 'C'. 'A' gives a positive iodoform
test 'A', 'B' and 'C' are given by the set :-
Br
(2)
CH CH2
(IV)
(1) II > I > III > IV
(2) I > III > IV > II
(3) I > II > III > IV
(4) I > IV > III > II
Arrange the following compounds in
decreasing order of Keq for nucleophilic
addition reaction.
O
(a) Ph—CO—CH3
Which of the following product will not be
obtained :-
Cl
(III) CH3 –CH=CH2
major
product
(1) CH3–CH(Br)CH2
(1)
8.
CH2=CH–NO2 (IV)
(2) III > II > I > IV
(4) II > III > IV > I
A is :–
4.
7.
Trans-2-butene HOBr P.
Identify the product P
CH3
CH3
OH
H
H
OH
(1)
(2)
H
Br
Br
H
CH3
CH3
CH3
CH3
CH3
Br
CH3
OH
(3) Br
(4)
H
H
HO
H
H
HCl
polymerisation
CH2=CH–C CH 1 eq. P
Q.
Product Q is :(1) Chloroprene
(2) Natural rubber
(3) Buna-S
(4) Neoprene
Arrange the following towards their reactivity
for hydration?
(I) CH 3O–CH=CH2 (II) F–CH=CH2
15
TARGET : PRE-MEDICAL 2021
11.
Which carbonyl group of the given compound
is most reactive for hydration :-
ORGANIC CHEMISTRY
CH2–CH=CH–CH3
NBS
15.
(A) .
Major
I
12.
(1) 3
(2) 1
(3) 2
(4) All have equal reactivity
Select the chain propagation steps in the free
radical chlorination of methane :.
(a) Cl2
2Cl
.
.
(b) Cl+CH4
CH3Cl+H
.
.
(c) Cl+CH4
CH3+HCl
.
.
(d) H+Cl 2
HCl+Cl
.
.
(e) CH3+Cl 2
CH3–Cl+Cl
Compound (A) is :
(1) Ph–CH2–CH=CH–CH2Br
Br
(2) Ph–CH–CH=CH–CH3
(3) Ph–CH2–CH 2–CH–CH 3
Br
(4) Ph–CH2–CH–CH2–CH3
Br
16.
(1) b, c, e
Match column-I and column-II and select the
answer :
Column-I
(2) a, c, e
Column-II
(a) CH3 –CH=CH2
?
C H 3 –C H – C H 3 (p) HBr followed
(3) c, e
Br
(4) b, c, d
13.
A hydrocarbon X(V.D.=35) forms only one
monochloro substitution product, X is :-
(b) CH3 –CH=CH2
?
CH 2–CH=CH2 (q) Br2 /CCl4
Br
(1) Neopentane
Br
(2) Cyclopentane
(c) CH3 –CH=CH2
?
C H 3 – C H – C H 2 (r) NBS
(3) Pent-1-ene
Br
(4) n-pentane
14.
by hydrolysis
Toluene reacts with Cl2 in the presence of light
(d) CH3 –CH=CH2
?
C H 3 – C H – C H 3 (s) HBr
OH
to give :–
(1) (a-s), (b-r), (c-q), (d-p)
(1) Benzyl chloride
(2) (a-p), (b-r), (c-q), (d-s)
(2) Benzoyl chloride
(3) (a-s), (b-q), (c-r), (d-p)
(3) p–chlorotoluene
(4) (a-q), (b-r), (c-s), (d-p)
(4) o–chlorotoluene
ANSWER KEY
Que. 1
3
Ans
Que. 16
1
Ans
16
2
2
3
2
4
3
5
2
6
1
7
4
8
4
9
3
10
2
11
3
Your Target is to secure Good Rank in Pre-Medical 2021
12
3
13
2
14
1
15
2
E
TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
REACTION MECHANISM ( PART-II )
1.
Correct order of rate of EAS (electrophilic
aromatic substitution) ?
NO2
Cl
RACE # 08
5.
The compounds P, Q and S
CH3
COOH
HO
(a)
(b)
(c)
(1) c > b > a > d
(3) a > b > c > d
2.
Q
HNO 3 /H 2 SO 4 mixt ure. The major product
formed in each case respectively, is COOH
(1)
NO2
(2)
NO2
HO
Cl
NO2
CH3
Cl
Which of following would not give 2-phenyl
butane as the major product in a Friedel Crafts
alkylation reaction with benzene?
(1) Butanoyl chloride + AlCl3 then Zn–Hg/HCl
(2) n-Butyl chloride + AlCl3
(3) 2-Butanol + H2SO4
(4) 1-Butene + HF
6.
O
Me
7.
Me
Br2
Fe
4.
HO
NO2
OCH3
NO2
H 3C
Me
Me
NH
(3)
C6H5
Me
(2) NO2—
—C—Br
C6H5
Me
Me
NH
(3) NC—
—C—Br
C6H5
Me
C6H5
(4)
Br
E
C6H5
Br
O
O
NH
NO2
C6H5
Br
Me
O
—C—Br
(2)
(1)
O
C6H5
O
Me
O
C
NO2
(1) RF > RCl > R –Br > R–I
(2) R–F > R –Br > R–Cl > R–I
(3) R–Cl > R –Br > R–F > R–I
(4) R–I > R –Br > R–Cl > R–F
Which one of the following is most reactive for
SN1 reaction :
(1) CH3O—
NH
O
C
The order of reactivity of the following alkyl
halides for a SN2 reaction is -
Major product of above reaction is :
O
O
NO 2
NO2
COOH
(4)
O
C
NO2
H3C
O
O2N
OCH3
HO
(4)
NH
H3C
COOH
CH3
(3)
O
C
OCH3
CH 2Cl
CH3
3.
NO2
COOH
(2)
CH3
(3)
OCH3
H3C
HO
CHCl2
CH 2Cl
S
were separately subjected to nitration using
; Compound (A) is :
(1)
O
H3C
(d)
CH3
OCH3
P
(2) c > d > a > b
(4) c > d > b > a
O
C
(4) CH3—
—C—Br
Br
Your Target is to secure Good Rank in Pre-Medical 2021
C6H5
17
TARGET : PRE-MEDICAL 2021
8.
Among the bromides given below, the order of
reactivity of S 1 reaction is N
12.
O
O
(I)
(II)
Br
Under identical conditions, solvolysis of which of
the following substrate would lead to maximum
racemisation :-
CH3
(III)
Br
(1) H
Br
Br
(2) III > II > I
CH3
H
(4) II > I > III
(I)
Br
(2)
Compare rate of S
I
1
N
I
:-
OCH3
I
(II)
CH3
(III)
(1) II > III > I
(3) I > II > III
10.
D
(1) III > I > II
(3) II > III > I
9.
ORGANIC CHEMISTRY
(3) Br
H
(2) II > I > III
(4) III > II > I
Br
(4) C6H 5
Reactivity order for SN1 reaction
Cl
Cl
(I)
NO2
D
CH3
13.
Which of the following alcohols is most reactive
towards substitution with HBr ?
(II)
C H 2O H
(1)
CH3
Cl
Cl
C H 2O H
(2)
(III)
CH2CH3
11.
(2) II > III > IV > I
(3) IV > III > II > I
(4) III > IV > II > I
Which of the following undergoes fastest
reaction with aqueous NaOH solution
(1) C6H5 CH
Cl
OMe
(2) C6H5 CH
Cl
CH3
(3) C6H5 CH
Cl
CH2CH3
C6H5 CH
Cl
C H 2O H
HC CH3
CH3
(1) I > II > III > IV
(4)
18
O 2N
(IV)
(3)
C H 3O
C H 2O H
(4)
Br
14.
Consider the following bromides :-
Me
Me
Br
Br
A
B
Me
Me
Br
C
The correct order of SN1 reactivity is
(1) A > B > C
(2) B > C > A
C6H5
(3) B > A > C
(4) C > B > A
Your Target is to secure Good Rank in Pre-Medical 2021
E
TARGET : PRE-MEDICAL 2021
15.
Of the following statements which are true for S
ORGANIC CHEMISTRY
1
N
17.
reaction.
.
(a) Tertiary alkyl halides react faster than
secondary.
Compound A is
(b) The absolute confuguration of the product
is opposite to that of the reactant when an
SH
optical active substrate is used.
(1)
(c) The reaction shows first order kinetics.
CH2SH
(d) The rate of reaction depends markedly on
the nucleophilicity of the nucleophile.
SH
(e) The mechanism is two step.
(2)
CH2Br
(f) Carbocations are intermediate.
(g) Rate
[Alkyl halides]
(h) The rate of the reaction depends on the
Br
nature of the leaving group.
(3)
CH2SH
CH3
16.
H
H
Br
D
NaOH,DMSO
Product.
CH3
(4)
Product .................is :18.
CH3
Which of the following reaction is feasible ?
OH
D
H
(1) H
CH3
Cl
–
+ AlCl4
(1)
AlCl3
CH3
HO
(2) H
H
D
CH3
Cl
(2)
Cl
CH3
Cl
Cl
Br
OH
H
(3) H
Cl
AlCl3
(3)
–
CH3
Cl
CH3
Cl
D
OH
H
(4) H
–
+ AlCl4
AlCl3
(4)
+ AlCl4
–
+ AlCl4
AlCl3
CH3
E
Your Target is to secure Good Rank in Pre-Medical 2021
19
TARGET : PRE-MEDICAL 2021
19.
Which reaction is least feasible
Cl
OH
22.
Which of the following on heating with
aqueous KOH, produces acetaldehyde ?
(1) CH2ClCH2Cl
NaOH
high temp
(1)
ORGANIC CHEMISTRY
Cl
(2) CH3CHCl 2
OH
(3) CH 3COCl
(4) CH3CH2Cl
NaOH
(2)
NO2
NO2
Cl
24.
R–OH
OMe
NaOH
(3)
Cl
OH
NO2
NO2
NaOH
(4)
NO2
21.
Reagent
R–OH
R–Cl
Which of the following reagents can be used
for this reaction.
(a) HCl/ZnCl2
(b) NaCl
(c) PCl3
(d) PCl5
(e) SOCl 2
(1) a, c, d, e
(2) a, b, c, d
(3) a, b, d, e
(4) All of the above
OH
OMe
20.
23.
NO2
Arrange the following in order of their leaving
group tendency?
O
Br
Ph-O
H3C C O
(I)
(IV)
(II)
(1) I > II > III > IV
(2) I >III > II > IV
(3) I > II > IV > III
(4) I > IV > III > II
The structure of the major product formed in
the following reaction is :
Cl
SOCl2
Pyridine
R–Cl + SO2 + HCl
This reaction follows which of the following
mechanisms ?
(1) SN1
(2) SN2
(3) E1
(4) E2
25.
NaCN
DMF
I
CN
F
(1)
A and B are :(1) Identical structure
(2) Position isomers
(3) Geometrical isomers
(4) None of the above
(2)
CN
CN
CN
Cl
(3)
(4)
CN
I
ANS W E R KE Y
Q ue.
1
2
3
4
5
6
7
8
9
10
11
12
13
Ans
4
3
1
4
3
4
1
1
2
2
1
2
3
Q ue.
Ans
Q ue.
Ans
14
2
23
1
16
2
17
3
18
3
19
3
20
3
21
4
22
2
20
15
a-T ,b-F,c-T ,d-F,e -T ,f-T ,g-T ,h-T
24
25
2
2
Your Target is to secure Good Rank in Pre-Medical 2021
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TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
REACTION MECHANISM (PART-II)
1.
RACE # 09
Which of the following is most reactive for
dehydrohalogenation :–
CH3
4.
NaNH 2
CH3–C–CH2–Cl
?
CH3
(1)
(2)
Br
Br
Br
Br
(3)
2.
(1)
(2) CH 3–C=CH2
CH 3
(4)
(3) CH3–C=CH–CH 3
CH3
In which of the following reaction saytzeff's
alkene is formed as major product :-
CH 3
alc.KOH
5.
CH3
A
Cl
Cl
(1) CH3–CH2 –C–CH3 OH
+ N(CH
(4) CH3 –CH=CH2
)
3 3
alc.KOH
B
Cl
Product A and B (major) are respectively :
CH 3
–
(2) CH3–CH2–CH–CH3 EtO/EtOH
F
(1)
CH3
CH3
(3) CH3–C–O–CH
CH2–CH3
O
(2)
CH3
CH3
(4) CH3–CH2–CH2–C–CH3
(3)
CH3O/CH3OH
CH3
Br
(4)
3.
CH2–CH–CH–CH3
|
|
Cl CH3
(1)
(2)
(3)
(4)
E
CH2–CH=C–CH3
|
CH3
alc. KOH
?
6.
Arrange the following towards their reactivity
for E2 elimination?
H3C
(I)
CH 2–CH2–C=CH2
|
CH3
CH=CH–CH–CH3
|
CH3
CH2–C=CH2
|
CH3
CH3
Br
CH3
Br
(II)
CH3
CH3
Br
(III)
CH3
(1) III > I > II
(2) I > II > III
(3) II > I > III
(4) III > II > I
Your Target is to secure Good Rank in Pre-Medical 2021
21
TARGET : PRE-MEDICAL 2021
7.
Cl
8.
10.
Given reaction mainly proceeds through –
CH 3ONa in
CH 3OH/
(1) E1
(2)SN1
(3) SN2
(4) E2
Match the column-I and column-II and select
the correct answer :
Column-I
Column-II
11.
Cl
a q. K O H
(a)
(p) E 1
In E 2 elimination some compounds follow
Hoffmann rule which means
(1) The double bond goes to the most
substituted position
(2) The compound is resistant to elimination
(3) No double bond is formed
(4) The double bond goes mainly toward the
least substituted carbon.
Identify the set of reagents/reaction conditions
'X' and 'Y' in the following set of
transformations :Y
Product
a lc . K O H
(b)
H 2O
Br
(1) X = dilute aqueous NaOH, 20°C,
Y= Br2/acetic acid, 20°C
(2) X = concentrated alcoholic NaOH, 80°C;
Y = HBr/CHCl3, 20°C
(3) X = dilute aqueous NaOH 20°,
Y = Br2/CHCl3, 0°C
(4) X = concentrated alcoholic NaOH, 80°C;
Y = Br2/CHCl3, 0°C
(r) S N2
OH
H /
(d)
CH 3–CH–CH3
(q) S N1
Cl
(c)
X
CH3–CH 2–CH 2Br
Cl
(s) E 2
(1) (a-s); (b-r); (c-p); (d-q)
12.
Maximum dehydration takes place that of O
(2) (a-r); (b-s); (c-q); (d-p)
OH
(3) (a-r); (b-s); (c-p); (d-q)
(1)
(4) (a-q); (b-p); (c-r); (d-s)
9.
ORGANIC CHEMISTRY
O
In the given reaction
(2)
OH
O
Product (Major)
(3)
The product will be
OH
CH2
(1) Cis-2-butene
(2) Trans-2-butene
(4)
(3) 2-butyne
OH
(4) Buta-1, 3-diene
ANSWER KEY
Que.
1
2
3
4
5
6
7
8
9
10
11
12
Ans
2
4
3
3
4
4
4
2
2
4
2
2
22
Your Target is to secure Good Rank in Pre-Medical 2021
E
TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
HYDROCARBON
RACE # 10
6.
O
The compound which produce propane on
heating with HI in presence of red P is
Zn-Hg
X
HCl
1.
HO
O
(a) CH 3CH2CH2I
Y; Y is :-
(b) CH3CH2CHO
(c) CH3CH2CH2OH
(1)
(d) CH3CH2COOH
(2)
(1) Only c (2) b, c
7.
OH
(3)
2.
1–Bromo–3–chloro cyclobutane on reaction
(1)
(2)
8.
(1) C6H6 (Benzene)
(2) C6H12
(3) C6H14
(4) CCl4
Give products of the following reactions :(i) O3
(ii) Zn/H2O
(a) CH2=CH2
Cl
Br
The compound that decolourises cold, dilute,
alkaline KMnO4 is :–
(4)
with 2–equivalent of sodium in ether gives
(3)
(4)
(b) CH3–C=CH2
3.
CaC2
D2O
A
Red hot
Cu tube
(i) O3
(ii) Zn/H2O
CH3
B; B is
CH 3
(3) b, c, d (4) All
(c) CH3 –C C–CH3
(i) O3
(ii) H2O
(2)
(1)
(i) O3
(ii) H2O
(d)
D
D
D
D
D
(3)
CD3
(4)
(f)
D
4.
(e) CH3 –CH=C=CH–CH3
CH 2 OHCH 2 CH 2 COCH 3
CH2
(i) O3
(ii) Zn/H2O
(i) O3
(ii) Zn/H2O
Re agent
CH2OHCH2CH2CH2CH3
(g)
Suitable reagent for above reaction is :–
5.
(1) Zn–Hg/HCl
(2) NH2NH2/C2H5ONa
(3) Red P + HI
(4) All
Which of the following alkane is synthesised
(h)
from single alkyl halide by wurtz reaction:-
CH3
E
(1)
(2)
(3)
(4)
(i) CH3–C=CH 2
KMnO4
(j) CH3–CH=CH–CH3
KMnO4
Your Target is to secure Good Rank in Pre-Medical 2021
23
TARGET : PRE-MEDICAL 2021
9.
Identify the hydrocarbon which on ozonolysis
gives :(a) Only acetone
(b) 1 equivalent of glyoxal + 1 equivalent of
propanedial
(c) 1 equivalent of CO 2 + 2 equivalent of
formaldehyde
(d) 1 equivalent of acetone + 1 equivalent of
acetaldehyde
12.
13.
ORGANIC CHEMISTRY
Among the following, the compound which has
highest boiling point is :(1)
(2)
(3)
(4)
Which of the following will react with 1-butyne ?
(1) AgNO3 + NH4 OH
(2) Cu2 Cl2 + NH4 OH
(3) Na
(4) All of them
10.
14.
?
The compound A is :(1) Benzene
(2) Duetero benzene
(3) Duetero toluene (4) Both (2) & (3)
11.
Cl2
CCl4
Ph–CH=CH–Ph
H2 Pd
BaSO4
2 NaNH 2
X
Y
(1)
(2)
(3)
(4)
Z
Product Z is
Ph
(1)
(3)
H
H
Ph
Ph
H
H
(2)
Ph
Ph C CH2
Ph
(4) Ph–C C–Ph
ANSWER KEY
Que.
1
2
3
4
5
6
7
10
11
12
13
Ans
Que.
Ans
2
14
3
3
3
2
4
4
2
2
2
3
4
8.
(a) 2HCHO
(b) CH3–C=O+HCHO
CH3
(h) CH3–C–C–H+H–C–C–H+CH3–C–C–CH3
O O
CH3
(i) CH3–C=O + CO 2
(c) 2CH 3–C–OH
O O
(j) 2 CH3–C–OH
(d)
O
O
O
O O
OH OH
O
9.
(a) CH3–C = C–CH 3
(b)
CH 3 CH3
(e) 2CH3 – CHO + CO2 (f)
O+HCHO
(c) CH2=C=CH2
(g) 3
24
CHO
CHO
(d) CH3–C=CH–CH 3
CH3
(Glyoxal)
Your Target is to secure Good Rank in Pre-Medical 2021
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TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
RACE # 11
HALOGEN, OXYGEN & NITROGEN CONTAINING COMPOUNDS
1.
Which of the following statement is true for the
major product obtained in the given reaction :CH4 + Cl2 h
OCOCH3
(major product) :-
(1) Reacts with AgNO3(aq) to give white ppt of
AgCl
(1) 2, 4 DNP
(2) Is used as an aneasthetic
(2) Lucas reagent (ZnCl 2) conc. HCl
(3) Has zero dipole moment
(3) NaHSO3
(4) Fehlings solution
(4) All
Among the following the one that gives positive
iodoform test upon reaction with I2 and NaOH is-
7.
(1) CH3CH2CH(OH)CH2CH3
(2) C6H5CH2CH2OH
CH3
(3) H3C
3.
OH
(4) PhCHOHCH3
In the following reaction sequence, the correct
structure of E, F and G are :
O
O
Ph
Heat
OH
(* implies
13C
[E]
(1) E =
Ph
, F=
CH3
Ph
Ph
CH3
Ph
, F=
CH3
,F=
5.
E
Ph
CH3
,F=
O Na
Ph
CH3
(3) CH3–C=NCONHNH2
O Na
Ph
O Na
, G = CHI3
O Na
, G = CH3I
(2) SO2Cl2/h
(3) SOCl2
(4) Cl2 , H2O
Which of the following is a feasible substitution ?
(3) R–Cl
AgF
(i) O2/
(ii) H3O
+
Q + phenol ,
P & Q are O
(1) Cl2, h
Hg 2 F2
P
AlCl3
, G = CHI3
Benzoyl chloride is prepared from benzoic acid
by -
(1) R–Br
CH3–CH2–CH 2–Cl
P
O
Ph
(4) CH3CH2CH=NCONHNH2
, G = CHI3
8.
O
O
(4) E =
(2) CH3–C=NNHCONH 2
CH3
O
O
(3) E =
(1) CH3CH2CH=NNHCONH2
[F] + [G]
O
O
(2) E =
I2
NaOH
Compound A (molecular formula C 3H 8O) is
treated with anhydrous CrO3 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 H2NCONHNH2, HCl
and sodium acetate gives a product C. Identify
the structure of C:-
labelled carbon)
O
4.
OCOCH3
(Q)
Product formed by (P) & (Q) can be differentiated
by
(Excess)
2.
Acidic
Hydrolysis
(P)
6.
(2) R–Br
(1)
and CH3–CH2–C–H
O
(2)
and CH3–C–CH3
O
(3)
and CH3–C–CH3
NaI
acetone
(4) All of these
O
(4)
and CH3–CH2–C–H
Your Target is to secure Good Rank in Pre-Medical 2021
25
TARGET : PRE-MEDICAL 2021
9.
O
In the following sequence of reactions
CH3CH2OH
P + I2
Mg
HCHO
B
Ether
A
C
H2O
ORGANIC CHEMISTRY
D
HCN
14.
A
LiAlH4
in ether
B
HNO2
C
In above reaction major product (C) is :
then compound 'D' is -
HO
(1) butanal
CH2OH
CH2OH
(1)
(2)
(2) n–butyl alcohol
OH
(3) n–propyl alcohol
(4) propanal
10.
(3)
: OH
Cl
PhCH2OH + PhCO2
the slowest step is :-
Mg
15.
Y
(1) Lactic acid
(2) Ethylamine
(3) Propylamine
(4) Alanine
16.
(3) Electrophile
(4) Acid
OH Cl
13.
CH3–CH–CH2 + Na
O
(1) CH3–CH–CH2
A
B , B is :
OH
(2) CH3–CH–CH2–CH3
OH
26
(4) Two moles of NaOH and two moles of Br2
Amine is obtained as major product in
CH3
Cl
(1)
NH3
(2) CH3–CH2–CH–CH3
NaNH2
NH3
Cl
O
(3) CH3–CH–CH2–OH (4) CH3–CH–CH2
CH3
Br
In the Hofmann bromamide degradation
reaction, the number of moles of NaOH and Br2
used per mole of amine produced are :
(3) Four moles of NaOH and two moles of Br2
17.
1.CH3MgCl
2. H3O+
(4)
(2) Four mole of NaOH and one mole of Br2
In above reaction CH3OH acts as :
(2) Base
Cl
(1) One moles of NaOH and one mole of Br2
18
(1) Nucleophile
C , C is :-
COOH
(3)
O
|| 18
R–C–O–CH3 + H2O
H+
+
H
(2)
COOH
COOH
Y in the above reaction is -
O
||
18
R–C–OH + HO–CH3
B
Cl
(1)
(4) The transfer of hydride to the carbonyl
group
X
CO2
COOH
(3) The attack of : OH at the carboxyl group
CH3CH2COOH
A
Br
(2) The deprotonation of PhCH2OH
Br2
Red P
THF
(1 mole)
(1) The abstraction of proton from the
carboxylic group
12.
(4)
In Cannizzaro reaction given below :2PhCHO
11.
O
OH
OH
(3) CH3–C–NH–CH3
LiAlH4
(4) All of these
Your Target is to secure Good Rank in Pre-Medical 2021
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TARGET : PRE-MEDICAL 2021
18.
The major product of the reaction is
22.
The presence of primary amine can be confirmed by these reactions with except :(1) HNO2
Major Product
NH2 OH
ORGANIC CHEMISTRY
(2) CHCl3+KOH
(1)
(2)
(3)
H
(4) H2 SO4
N
(4)
O
(3) CS2 and HgCl2
OH
H
19.
Which of the following compound can form
hydrazone and will give iodoform test but will not
give Tollen's test ?
O
C
(1)
20.
23.
The major product formed in this reaction :CH2 CH3
(2) H3C C CH2 CH3
O
(3) H3C C CH2 CHO
O
(4) CH3 –CH 2 –OH.
(1)
Which one of the following compounds will
not be soluble in sodium bicarbonate ?
(2)
(1) Benzene sulphonic acid
(2) Benzoic acid
(3) o-Nitrophenol
(3)
(4) 2,4,6-Trinitrophenol
21.
Find out correct sequence of reagent for
following conversion :
24.
(4) None of these
Match the following :
a Phenol + Neutral FeCl3
p No reaction
(1) PCl5, CH3MgBr
b Phenol + Br2 (aq.)
q Violet colour
(2) CH2N2, NaBH4
c Phenol + NaHCO 3
r White ppt.
(3) SOCl2, H2/Pd,BaSO4
d Picric acid + NaHCO 3
s CO 2 gas is evolved
(4) All of the above
ANSWER KEY
Que.
1
2
3
4
5
6
7
8
9
10
11
12
13
Ans
3
4
3
3
4
4
1
3
3
4
4
1
2
Que.
Ans
14
4
15
2
16
2
17
3
18
3
19
2
20
3
21
3
22
4
23
1
E
Your Target is to secure Good Rank in Pre-Medical 2021
24
a-q, b-r, c-p, d-s
27
TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
BASED ON CONVERSIONS
RACE # 12
(i) B H 3 , T H F
1.
CH3 – CH = CH2
P C l5
X
(ii) H 2O 2/O H
5.
HBr
CH3 –C CH
X
a q. K O H
Z n -H g
Y
Z
HCl
Which of the following is true regarding Z ?
Y; Y is
(1) Its all carbon atoms are sp 3 hybridised
(1) CH3 – CH2 – CH2 – Cl
(2) It can be obtained in good yield by Wurtz
reaction.
(2) C H 3 – C H – C H 3
Cl
(3) It shows isomerisation reaction with
HCl/AlCl3 .
Cl
(3) C H 3 – C H 2 – C H
(4) All
Cl
6.
Cl
CH2=CH2
Baeyer 's
reagent
PCl 5
P
Q
NaNH 2
1mole
R.
Which of the following statement is true
regarding R?
(4) CH3 – C – CH3
Cl
(1) Has more dipolemoment than ethylchloride.
2.
O z o n o ly si s
CH 3 – CH = CH – CH 3
X
(2) Has more C-X bond length than
ethylchloride
(i) alc. K O H
P C l5
Y
Z; Z is
(ii) N aN H 2
(3) Is less reactive than ethylchloride for SN reaction.
(2) C H 3 – C H
(1) CH 3 – CH = O
(3) CH2 = CH – Cl
(4) HC
Cl
(4) All.
Cl
7.
CH
C H 3– C H – C H 3
alc. KOH
X
HBr
R 2O 2
Y
KI
A c eton e
Z
I
(P )
N a O H /C a O
O
3.
P
Initial compound (P) and the last product Z
are :-
R;
CH 3 – C – OH
(i) A g O H
(ii) B r 2/C C l 4
X
(1) Chain isomers
(2) Position isomers
(3) Homologues.
(4) Identical.
Reagent R can not be:
KCN
(1) LiAlH4
(2) Na + (C2 H5)2 O
(3) Zn + HCl
(4) All
8.
CH3 – CH3
B r2
h
AgCN
4.
CH3 – C H – CH = CH2
(P )
R
PC l 3
(A lco h o l)
S
C H 3O N a
T
.
(A lk y lch lo r id e) (E th er)
Which of the following should be used as Q to
get ether (T) in good yield ?
(1) H3O
(2) (i) (CH3COO)2 Hg, H2O (ii) NaBH 4
(3) (i) BH3, THF (ii) H2 O2 / OH
(4) All
28
H 3O
S
P
CH3
Q
Q
R
H 3O
T
The products S & T can be obtained by
ozonolysis of :
(1) CH 3 – CH2 – C
(2) CH 3 – C
CH
(3) CH 3 – CH2 – C
(4) CH 3 – C
C – CH2 – CH3
CH
C – CH3
Your Target is to secure Good Rank in Pre-Medical 2021
E
TARGET : PRE-MEDICAL 2021
9.
Which of the following reaction gives 3º
alcohol
O
H
CH3CN
A ether B
H3O
C
D.
Product D is
COCH 3
(ii) H3O
(1)
(i) CH3MgBr
(2) CH 3 – CN
Mg
NBS
12.
(i) MeMgBr
(1)
ORGANIC CHEMISTRY
(2)
COCH3
(ii) H3O
COOH
O
(4)
COOH
(ii) H3O
O
(4) CH3 – CH – CH2
10.
(3)
(i) CH3MgBr (excess)
(3)
13.
(i) CH3MgBr
O
In which of the following group, each member
can be reduced to alcohol by using NaBH4 :
O
O
NH 3
A
Br2
KOH
B
C
Structure of compound C is
(1) CH3CH2 CH2 NH2 (2) CH3 CH2 NH2
(3) CH3 CH2NHCH3 (4) CH3 CH2CONH2
(ii) H3O
(1) CH3 – C – Cl, CH3 – C – OH, CH3 – C – NH2
SOCl 2
CH3CH2COOH
O3
H2 O
14.
i Ca OH
ii
A
2
B
O
Product B is
(2) CH3 – C – H, CH3 – C – CH3 , C H 3– C – C 2 H 5
O
C
O
O
O
(1)
H
O
(2)
(3) CH3 – C – H, CH3 – C – OC2H5 , CH3 – C – Cl
O
O
O
(3)
(4) CH3 – C – CH3 , CH3 – C – NH2, CH3 – C – H
O
O
11.
O
15.
The end product E would be -
O
O
(4)
Which of the following reaction is not correct
according to major product
CH3
Br2
FeBr3
B
Sn+HCl
C
NaNO2
HCl
CuBr
HBr
D
CHO
E
(1)
CHO
NO 2
COONa
(2) H3C CH2 CH CH3
Br
(1)
OH
CH3
CH2–Br
CH3–CH=CH–CH3
F
(2)
O
Br
Br
(3)
OH
CH3
HI
+CH3–I
CH3
CH3
Br
Br
Br
(3)
(4) Cl3C–C–H
O
(4)
Br
E
CH2
conc. NaOH
NaOH
CHCl3 + HCOONa
Br
Your Target is to secure Good Rank in Pre-Medical 2021
29
TARGET : PRE-MEDICAL 2021
1. O3
2.Zn,H2 O
16.
(A)
1. OH /
(P)
2. H
ORGANIC CHEMISTRY
Mg
Dry ether
18.
Product 'P' will be :-
NaHCO3
(1) CHO
(A)
(i) 14 CO2
ii H / H 2 O
(B)
(C) gas, product C is :-
(1) CO
COOH
(2)
(2) CH2OH
14
CO2
(3) CO2
COOH
(4) A mixture of
(3) CH2–OH
19.
CH2–OH
14
CO2 and CO2
(P) and (Q) in the following reaction is
(4) COOH
COOH
17.
Identify major product of following sequence of
reaction :
OH ,
(1)
OH
O
O
(2)
(3)
(1)
(4)
20.
(2)
In the given reaction sequence
C6H5NO2 Sn/HCl P NaNO2/HCl Q CuCN/HCN R H2O/H S
which one statement is not correct ?
(3)
(1) P is C6H5 NH2
(2) Q is C6H5 – N
(4)
N Cl
(3) R is C 6H 5CH 2CN
(4) S is C6H5COOH
ANSWER KEY
Que.
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
Ans
1
4
2
3
1
3
2
3
3
2
2
2
2
2
2
17
3
18
3
19
4
20
3
Que. 16
2
Ans
30
Your Target is to secure Good Rank in Pre-Medical 2021
E
TARGET : PRE-MEDICAL 2021
ORGANIC CHEMISTRY
NCERT CONVERSIONS
1.
RACE # 13
Find A & B
6.
SOCl2 .Pyridine
CH3 CH2 OH
HC CNa
A
Br
B
Sodium acetylide
Ethanol
2.
Find A, B & C
A
Br2 /H2 O
NaNO 2/HCl
B
Br
1,3,5 - Tribromobenzene
KCN (alc)
A
Bromomethane
CH3–MgBr
B
Hydrolysis
H3 O+
C
7.
Find A, B & C
H3O
Hydrolysis
CH3 (CH)4 CN
Hexanenitrile
Find X & Y
Br2 / KOH
CH2Cl
X
PCl5
8.
CH2CN
HNO2
N2 , H 2 O
9.
(Hydrolysis)
NH 3
Br2 / KOH
A
K 2Cr2O7 / H2 SO4
C
Y
HNO2
CH3CH2
C2H5 OH
H ,
D
OH
[O]
CH3COOH
CH3–COOC2H5
Find A & B
10.
Br
CH3–C–CH3
KOH(alc)/
Dehydrohalogenation
A
HBr/Peroxide
Find X
X
B
HNO2
N2 , H2O
CH3
HI
O CH 3
CH3 I
Methyliodide
CH3
Tert-Butylbromide
5.
B
Find X
X
+
H /H2O
B
Find A, B & C
Propanoic acid
Benzyl cyanide
NH3
A
C
CH3 CH2COOH
KCN, Aq. ethanol –KCl
4.
H3 PO2
Find A, B & C
CH3 – Br
3.
C
Br
KCN
KI
CH3 CN
Na / C2 H5 OH
Reduction
CH3 CH2 NH2
Ethanamine
Find X & Y
+ –
N2Cl
X + NaNO2 + 2HCl
11.
273-278 K
CH3
Find A, B, C & D
A
+ NaCl + 2H2O
(i) Fe/HCl
B
NaNO2 /HCl
273-278 K
C
CuCN/HCN
D
H 3O
HBF 4
Hydrolysis
COOH
Y
NaNO2 Cu,
NO2
NaBF4 + N2 +
Benzoic acid
CH3
3-Nitrotoluene
12.
Find A, B & C
NH2
Br2/H 2O
A
NaNO 2/HCl
273-278 K
B
HBF4
Heat
C
Aniline
E
Your Target is to secure Good Rank in Pre-Medical 2021
31
TARGET : PRE-MEDICAL 2021
13.
Find A, B & C
15.
Find A, B, C, & D
NH2
Conc.HNO3
+Conc.H 2SO 4
NaNO2/HCl
273-278 K
A
H 3PO2
B
CH3Cl
Anhyd. AlCl 3
Aniline
333 K
C
ORGANIC CHEMISTRY
A
Benzene
Cl2(1 mole),hv 383 K
Br2/Fe
B Sn + HCl C
NaNO2/HCl 273-278 K
E
Boiling
dil H2SO 4
D
CH2OH
KOH (aq.)
(Hydrolysis)
D
Benzylalcohol
14.
Find A, B & C
CONH2
Br2/NaOH
Heat
A
NaNO2 /HCl
273-278 K
Diazotisation
B
H3PO2
C
Benzamide
CH3Cl/Anhyd.AlCl3
CH3
Toluene
CONH2
or
32
COOH
+
H /H2O
CH3
Red P
HI
Your Target is to secure Good Rank in Pre-Medical 2021
E
TARGET : PRE-MEDICAL 2021
NCERT CONVERSIONS
RACE # 14
1.
Give the structures of A, B and C in following
reaction ?
(i)
CH3CH2I
NaCN
2.
How will you bring about the following
conversions in not more than two steps ?
(i) Ethanol to 3-Hydroxybutanal
B
(ii) Bromobenzene to 1-Phenylethanol
NaOH Br2
(ii)
OH –
Partial hydrolysis
A
ORGANIC CHEMISTRY
C
(iii) Benzaldehyde to 3-Phenylpropan-1-ol
NH3
CH3COOH
NaOBr
A
(iv) Benzene to m-Nitroacetophenone
B
(v) Benzyl chloride to 2-phenylethanamine
NaNO2 / HCl
(iii)
C
Fe / HCl
C6H5NO2
C6 H 5 OH
B
C
(iv)
HC CH
Red hot
Fe tube
(v)
CH3NO2
A
(vi)
HNO2
273K
A
Br2/Fe
dark
A
CH3NH 2
COOH
B
B dryNa
C
ether
CH3NC
COCl
A
C
CH3NHCH3
CONH2
B
NH2
C
Cl
(vii) CH3–CH–CH3 A CH3–CH=CH2 B
CH3CH2CH2OH C CH3CH2CH2Br
(i) CH 3MgBr
KCN
A (ii) H O/H
(viii) CH3Cl
B
Ba (OH)2
C
2
COOH
(ix)
Mg
A dry ether B
CO2
C
H3O
CHO
(x)
KMnO 4
A
SOCl2
B Anhydrous C
AlCl3
E
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33