1
LAKSHYA JEE 2023
Alcohol, Phenol and Ethers
1.
Which of the following compounds on reaction with
excess of CH3MgBr will give a tertiary alcohol?
6.
The reagent required to convert propene to 1propanol is
(1) B2H6 followed by H2O2/NaOH
(2) conc. H2SO4 followed by hydrolysis with
boiling water
(3) HBr followed by hydrolysis with aqueous
KOH
(4) Hg(OCOCH3)2 followed by reduction with
NaBH4
7.
Reaction of
(1)
2.
3.
(2)
C2 H5CO 2 CH3
(3)
C6 H5CHO
(4)
C2 H5COOH
Oxymercuration-demercuration reaction of
1-methylcyclohexene gives
(1) trans-2-methyl cyclohexanol
(2) cis-2-methylcyclohexanol
(3) 1-methyl cyclohexanol
(4) mixture of cis- and trans-2-methylcyclohexanol
The product of the following reaction is
DPP-02
with RMgX followed by
acid hydrolysis will lead to produce
(1) RCHOHR
(2) RCHOHCH3
(3) R2CHCH2OH
(4) RCH2CH2OH
8.
( i )BH /THF
( ii )H 2O2 ,OH
CH3MgBr( excess )
Ethyl ester → P.
The product P will be
3

→
(1)
(2)
(3)
(4)
4.
5.
2-pentanol
pentane
pentan-2-one
1-pentanol
The reaction of Grignard reagent with formaldehyde
followed by acidification gives
(1) An aldehyde
(2) A ketone
(3) A carboxylic acid
(4) A primary alcohols
9.
(1)
(2)
(3)
(4)
When one of the following compounds will react with
Grignard reagent to yield a primary alcohol containing
two more carbons?
(1) CH3CHO
(2)
(3)
HCHO
(4)
CH3COCH3
What is the major product of the following
reaction?
CH MgI
Et 2O
3

→
(1)
(3)
H3O⊕

→
10.
(2)
(4)
Sum of number of 1° alcoholic groups in product
(P) and (Q) is:
(1) 1
(2) 2
(3) 3
(4) 4
2
11.
Predict the product when given compound reacts
with LiAlH4:
14.
Which one of the following will produce a primary
alcohol by reacting with CH3MgI:
(1)
Acetone
(2)
Methyl cyanide
(3)
Ethylene oxide
(4)
Ethyl acetate
(1)
−
B2 H 6
H 2O2 /OH
→ B 
→ Isobutyl alcohol, A is
15. A 
(1) Isobutane
(2) 2-Methyl Propene
(3) 𝛽𝛽-Butylene
(4) 𝛼𝛼-Butylene
(2)
16. The only alcohol that can be prepared by the
hydration of ethene is
(1) Ethyl alcohol
(2) Propyl alcohol
(3) Isobutyl alcohol
(4) Methyl alcohol
(3)
(4)
12.
product (A) is:
(1)
(2)
H 2O, Hg(OAC)2
CH CH 2 
→(A),
17. CH3 − CH − =
NaBH 4
|
CH 3
(1) predominantly is
(1)
CH 3 − CH − CH 2 − CH 2 − OH
|
CH 3
(2)
CH 3 − CH − CH − CH 3
|
|
CH 3 OH
(3)
(3)
(4)
OH
|
CH 3 − C − CH 2 − CH 3
|
CH 3
(4) CH3–CH2–CH2–CH2–CH2–OH
13.
Propene, CH3–CH=CH2 can be converted to 1propanol by oxidation. Which set of reagents among
the following is ideal to effect the conversion:
(1) Alkaline KMnO4
(2) B2H6 and alkaline H2O2
(3) O3/Zn dust
(4) OsO4/ CH4, Cl2
CH 3
CH 3
|
|
18. CH 3 − C −
=
CH CH 2 
→ CH 3 − C − CH − CH 3
|
|
|
CH 3
CH 3 OH
This change can be done by
(1) acid catalysed hydration
(2) oxymercuration-demercuration
(3) hydroboration-oxidation
(4) any method mentioned above
3
(4) Oxymercuration demercuration, hydroboration
oxidation and hydration
19.
Identify the major product ‘P’ is
(1)
(3)
23.
A is
(2)
(1)
(2)
(3)
(4)
(4)
20. RCH = CH2 adds on water in the presence of dilute
sulphuric acid or phosphoric acid to form
(1) R—CH(OH)—CH3
(2) R—CH2—CH2OH
(3) R—CHOH—CH2—CH2—CHOH—R
R — CH— CH 2
|
|
OH
OH
(4)
21. The major product of the following reaction is
24.
Reagent ‘A’ is
(1) BH3/H2O2/ ΘOH
(2) H2O/HΘ
(3) Hg(OCOCH3)2/NaBH4
(4) Cl2
25. In the given reaction
(1)
[X] will be
(1) LiAlD4/D2O
(2) NaBD4/H2O
(3) LiAlD4/HOH
(4) NaBH4/D2O
(2)
(3)
26.
When CH2 = CH–COOH is reduced with LiAlH4,
the compound obtained will be
(1) CH3–CH2–CH2OH
(2) CH3–CH2–CHO
(3) CH3–CH2–COOH
(4) CH2 = CH–CH2OH
27.
The hydroboration of 2-methyl propene yields
(1) 1° alcohol
(2) 2° alcohol
(3) 3° alcohol
(4) None
28.
LiAlH4 converts acetic acid into
(1) Acetaldehyde
(2) Methane
(3) Ethyl alcohol
(4) Methyl alcohol
29.
A tertiary alcohol is obtained when CH3MgI reacts
with
(1) CH3CHO
(2) CH3CH2CHO
(4)
22. X, Y, Z reaction are
(1) Simple hydration reaction
(2) Hydroboration oxidation, hydration and
oxymercuration demercuration
(3) Hydroboration oxidation, oxymercuration
demercuration and hydration
4
(3)
30.
CH 3 − CH − CHO
|
CH 3
(4) CH3COCH3
To prepare 3-ethylpentan-3-ol, the reactants needed
are
(1) CH3CH2MgBr + CH3COCH2CH3
(2) CH3MgBr + CH3CH2CH2COCH2CH3
(3) CH3CH2MgBr + CH3CH2COCH2CH3
(4) CH3CH2CH2MgBr + CH3COCH2CH3
31.
32.
(1)
(2)
(3)
(4)
35.
How many moles of alkene are required with one
mole of diboarane in the formation of alcohol from
hydroboration-oxidation
(1) 2
(2) 3
(3) 4
(4) 5
Choose the major product of the following reaction
36.
When ketones are treated with Grignard reagent
followed by hydrolysis with dilute acid, the product
is
(1) Primary alcohol (2) Secondary alcohol
(3) Tertiary alcohol (4) Alkene
(1)
(2)
37.
(3)
(4)
Propene on hydroboration oxidation produces
(1) Propan-1-ol
(2) Propan-2-ol
(3) Propane-1, 3-diol
(4) Propane-1, 2-diol
38.
Consider the following reaction
PBr
The following compound on mercurationdemercuration produces the major product
(1)
(2)
(1)
(3)
33.
34.
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 H2O, NaOH
(2) H2O, H2SO4
(3) Br2, H2O
(4) Hg (O2CCH3)2, followed by NaBH4, NaOH
(i) H SO
2 4→Z
Y 
(ii) H O, ∆
2
39.
(3)
(4)
alc.KOH
3 → X 
Ethanol 
→
The product Z is
(1) CH3CH2OCH2CH2
(2) CH3CH2O – SO3H
(3) CH3CH2OH
(4) CH2 = CH2
40.
(2)
Both
(4)
None
(2)
(4)
benzyl alcohol
none
LiAlH
4→
C6 H5CHO 
(1)
(3)
41.
benzene
phenol
Identify the reagent used in the following
conversion
What is the major product of the following
reaction?
(1)
(3)
LiAlH4
both
(2)
(4)
NaBH4
none
5
(4)
42.
43.
Ketone on reduction with sodium borohydride gives
(1) primary alcohol (2) secondary alcohol
(3) tertiary alcohol
(4) none
Reagent used for the following conversion is
(1)
(3)
44.
LiAlH4
both
(2)
(4)
NaBH4
none
1-Phenylethanol can be prepared by the reaction of
benzaldehyde with
(1) Methyl bromide
(2) Ethyl iodide and magnesium
(3) Methyl iodide and magnesium (Grignard
reagent’s)
45.
Methyl bromide and aluminium bromide
Which of the following alcohols will give the most
stable carbocation during dehydration?
(1) 2-methyl-1-propanol
(2) 2-methyl-2-propanol
(3) 1-Butanol
(4) 2-Butanol
6
Answer Key
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
(2)
(3)
(4)
(4)
(4)
(1)
(4)
(1)
(2)
(4)
(3)
(4)
(2)
(3)
(2)
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
(1)
(2)
(2)
(3)
(1)
(3)
(3)
(3)
(1)
(1)
(3)
(1)
(3)
(4)
(3)
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.
41.
42.
43.
44.
45.
(2)
(1)
(4)
(2)
(2)
(3)
(1)
(3)
(2)
(2)
(1)
(2)
(3)
(3)
(2)
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