1
YAKEEN 2.0_2023
Alcohol, Phenol and Ether
OH
|
1.
6.
The compounds A, B and C in the reaction sequence
are given by the set:
( i ) CH3CHO
HBr
Mg
CH3CH 2OH ⎯⎯⎯
→ A ⎯⎯⎯
→ B ⎯⎯⎯⎯⎯
→C

( ii ) H3O
(1) CH3CH2Br,CH3CH2MgBr, (CH3)3C—OH
(2) CH3CH2Br, (CH3CH2)2Mg,
(CH3)2CHCH2OH
(3) CH3CH2Br, CH3CH2MgBr,
CH3CH(OH)CH2CH3
(4) CH3CHBr2, CH3CH(MgBr)2, CH3CH(OH)CH3
7.
The reaction of ethylmagnesium iodide with
acetaldehyde gives after acidification
(1) 2-Butanol
(2) 1-Butanol
(3) 2-Methyl-2-propanol
(4) 2-Methylpropanol
8.
To prepare 2-propanol from methyl magnesium
bromide, the other chemical required is
(1) HCHO
(2) CH3CHO
(3) C2H5OH
(4) CH3COCH3
9.
In the reaction (CH3)2–CHCH=CH2
CH3CH 2 − C − CH3 cannot be prepared by
|
Ph
(1)
(2)
(3)
(4)
2.
DPP-01
CH3CH2COCH3 + PhMgX
PhCOCH3 + CH3CH2MgX
PhCOCH2CH3 + CH3MgX
HCHO + PhCH(CH3) CH2MgX
The major product of the following reaction is
LiAlH
4→
CH 3 CH = CHCO2CH3 ⎯⎯⎯⎯
(1) CH 3 CH = CHCH 2OH
(2) CH 3 CH 2CH 2 CH 2 OH
(3) CH 3 CH 2CH 2CO2 CH3
(4) CH 3 CH 2CH 2CHO
3.
Which of the following compounds on reaction with
excess of CH3MgBr will give a tertiary alcohol?
(1)
(2) C2H5CO2CH3
(3) C6H5CHO
(4) C2H5COOH
4.
5.
BH /THF
3
⎯⎯⎯⎯⎯⎯
−→
Oxymercuration-demercuration reaction of
1-methylcyclohexene gives
(1) Trans-2-methyl cyclohexanol
(2) Cis-2-methylcyclohexanol
(3) 1-methylcyclohexanol
(4) Mixture of cis- and trans-2-methylcyclo-hexanol
The product of the following reaction is
(i) BH /THF
3
⎯⎯⎯⎯⎯⎯
−→
(ii) H 2O2 , OH
(1)
(2)
(3)
(4)
2-pentanol
pentane
pentan-2-one
1-pentanol
(ii) H 2O2 /OH
(1)
(2)
(3)
(4)
10.
(CH3)2–CH–CH2–CH2OH
(CH3)2–CH–CH(OH)–CH3
(CH3)2–C(OH)–CH2–CH3
CH3–CH(OH)–(CH2)2–CH3
In the reaction (CH3)2–CH–CH2Cl
aqueous KOH
⎯⎯⎯⎯⎯⎯
→ A (Major) A will be
(1) (CH3)2–CH–CH2OH
(2) (CH3)3–C–OH
(3) CH3–CH(OH)–CH2CH3
(4) (CH3)2–C=CH2
11.
In the reaction (CH3)2–CH–CH=CH2
H O/H +
2
⎯⎯⎯⎯
→ A, A will be:
(1) (CH3)2–CH–CH2–CH2OH
(2) (CH3)2–CH–CH(OH)–CH3
(3) (CH3)2C(OH)CH2CH3
(4) CH3CH(OH)CH2CH2CH3
12.
13.
Which of the following alkenes to give same product
in HBO, Oxymercuration–demercuration and acid
catalyzed hydration?
(1)
(2)
(3)
(4)
16.
on reaction with
(1) CH3–CHO
(2)
(3) CH3–CH2–CHO (4)
17.
Select schemes A, B, C out of
I.
II.
III.
(1)
(3)
The following compound on mercurationdemercuration produces the major product
Acid catalyzed hydration
HBO
Oxymercuration-demercuration
I in all cases
(2) I, II, III
II, III, I
(4) III, I, II
18.
To prepare 3-ethylpentane-3-ol, the reactants needed
are
(1) CH3CH2MgBr + CH3COCH2CH3
(2) CH3MgBr +CH3CH2CH2COCH2CH3
(3) CH3CH2MgBr + CH3CH2COCH2CH3
(4) CH3CH2CH2MgBr + CH3COCH2CH3
19.
In the reaction sequence,
(1)
(2)
forms
H O
dil.H SO
H
2 → A ⎯⎯⎯⎯⎯
2
4
2⎯
CaC2 ⎯⎯⎯
→ C,
+2 → B ⎯⎯
Ni
Hg
the product C is
(1) CH3OH
(3) C2H5OH
(3)
(4)
14.
15.
Which set of reagents is used for the purpose of
adding water to an alkene in a Markovnikov addition
without rearrangement?
(1) BH3, THF followed by H2O2, NaOH, H2O
(2) H2O, H2SO4
(3) Br2, H2O
(4) Hg (OAc)2, H2O followed by NaBH4
How many moles of alkene are required with one
mole of diborane in the formation of alcohol from
hydroboration-oxidation
(1) 2
(2) 6
(3) 4
(4) 5
20.
(2) CH3CHO
(4) C2H4
A and B are
(1)
(2)
(3)
(4)
in both cases
in both cases
Note: Kindly find the Video Solution of DPPs Questions in the DPPs Section.
Answer Key
1.
(4)
11.
(3)
2.
(1)
12.
(3)
3.
(2)
13.
(1)
4.
(3)
14.
(4)
5.
(4)
15.
(2)
6.
(3)
16.
(2)
7.
(1)
17.
(3)
8.
(2)
18.
(3)
9.
(1)
19.
(3)
10.
(1)
20.
(2)
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1
YAKEEN 2.0_2023
Alcohol, Phenol and Ether
1.
2.
Ethanol when reacted with PCl5 gives A, POCl3 and
HCl. A reacts with silver nitrite to form B (major
product) and AgCl. A and B respectively are
(1) C2H5Cl and C2H5NO2
(2) C2H6 and C2H5NO2
(3) C2H5Cl and C2H5OC2H5
(4) C2H6 and C2H5OC2H5
5.
In this reaction
H SO , heat
2
4
⎯⎯⎯⎯⎯
→
160 C
?
The major products formed are
(1)
An alcohol C5H11OH on dehydration gives an alkene,
which on oxidation yield a mixture of a ketone and
an acid. The alcohol is
(1) CH3 − CH − CH 2 − CH 2 − CH3
(2)
(3)
|
OH
(2) CH3 − CH − CH − CH3
|
DPP-02
(4)
|
CH3 OH
(3) CH3CH2CH(OH)CH2CH3
(4) None of these
3.
What is the major product of this reaction?
KMnO
4 →
⎯⎯⎯⎯⎯
KOH, H O
6.
?
H SO
B H
Here R is:
(1) ethyl cyclohexane
(2) 2-propyl cyclopentene
(3) 2-propyl cyclopentanol
(4) 1-propyl cyclopentanol
(1)
(2)
7.
Give the decreasing order of the reaction rates of the
following compounds with HBr.
I.
(3)
II.
(4)
III.
4.
H O /OH −
2 6
2
4 → P ⎯⎯⎯
2 2
⎯⎯⎯⎯
→ Q ⎯⎯⎯⎯⎯
→R
2
In the following sequence of reactions,
P + I2
Mg
CH3CH 2OH ⎯⎯⎯
→ (A) ⎯⎯⎯
→ (B)
Ether
HCHO
IV.
H 2O
⎯⎯⎯⎯
→ (C) ⎯⎯⎯
→ (D)
The compound (4) is:
(1) n-butyl alcohol (2) n-propyl alcohol
(3) propanal
(4) butanal
(1)
(2)
(3)
(4)
I > II > III > IV
IV > III > III > I
II > I > III > IV
IV > III > I > II
8.
In the given pair of alcohol, in which pair second
alcohol is more reactive than first towards hydrogen
bromide?
12.
(1)
(2)
Select the incorrect statement about hydroborationoxidation.
(1) Addition is against Markovnikov’s rule
(2) Intermediate is a carbocation
(3) It does not involve rearrangement
(4) Addition of boron and hydrogen to double bond
is a syn-addition
13.
(1), Product (1) is:
(1)
(3)
(2)
(4)
(3)
9.
In which of the following reactions hydrogen gas will
not be evolved?
Na
(1) CH3CH 2OH ⎯⎯→
(4)
14. What is the major product of the following reaction?
OH
Na
(2) CH3CH 2CH 2OH ⎯⎯→
CrO
CH3 – CH – CH2 – CH 2 – OH Pyridine3 cold A Product
OH
O
Al
⎯⎯→
(3)
(1) CH3 – CH – CH2 – C – H
CH3MgBr
⎯⎯⎯⎯⎯
→
(4)
O
O
(2) CH3 – C – CH2 – C – H
O
10.
B
NaBH4
CH=CHCHO
A and B respectively are
(1)
CH CH CHO,
2
(2)
H2/Pt
2
(3) CH3 – C – CH2 – C – OH
A
OH
O
(4) CH3 – CH – CH2 – C – OH
CH=CHCH2OH
CH2CH2CH2OH
CH – CO 2Et
CH=CH–CH2–OH
CH – CH 2OH
(A)
15.
CH=CH–CH2–OH
(3)
O
Identify A and B
(1) A = NaBH4, B =
in both cases
CH2CH2CH2OH
(4)
(2) A = NaBH4, B =
in both cases
11.
CH3
(3) A = LiAlH4, B =
CH2 Changes to
(1) H3O

(3) LiAlH4
OH
(2) BH3.THF/H2O2, NaOH
(4) NaBH4
(4) A = LiAlH4, B =
MnO2
(B)
Note: Kindly find the Video Solution of DPPs Questions in the DPPs Section.
Answer Key
1.
(1)
9.
(4)
2.
(2)
10.
(2)
3.
(2)
11.
(1)
4.
(2)
12.
(2)
5.
(1)
13.
(3)
6.
(3)
14.
(2)
7.
(1)
15.
(3)
8.
(4)
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