Chapter 25

Alcohols, Phenols and Ethers

1. The major product obtained on interaction of phenol 6. An unknown alcohol is treated with the "Lucas
with sodium hydroxide and carbon dioxide is: reagent" to determine whether the alcohol is
[AIEEE-2009] primary, secondary or tertiary. Which alcohol reacts
(1) Salicylaldehyde (2) Salicylic acid fastest and by what mechanism ?
[JEE (Main)-2013]
(3) Phthalic acid (4) Benzoic acid
(1) Secondary alcohol by SN1
2. From amongst the following alcohols the one that
(2) Tertiary alcohol by SN1
would react fastest with conc. HCl and anhydrous
ZnCl2, is [AIEEE-2010] (3) Secondary alcohol by SN2

(1) 1-Butanol (2) 2-Butanol (4) Tertiary alcohol by SN2

(3) 2-Methylpropan-2-ol (4) 2-Methylpropanol 7. Sodium phenoxide when heated with CO2 under
pressure at 125°C yields a product which on
3. The correct order of acid strength of the following acetylation produces C.
compounds is [AIEEE-2011]
— ONa 125° H
+

A. Phenol + CO2 B C
5 Atm Ac2O
B. p-Cresol
C. m-Nitrophenol The major product C would be [JEE (Main)-2014]

D. p-Nitrophenol OCOCH3 OH
(1) A > B > D > C (2) C > B > A > D COOH COCH3
(1) (2)
(3) D > C > A > B (4) B > D > A > C
4. Consider the following reaction
COCH3
C2H5OH + H2SO4 o Product
OH OCOCH3
Among the following, which one cannot be formed
as a product under any conditions? [AIEEE-2011] COOCH3
(3) (4)
(1) Diethyl ether COOH
(2) Ethyl-hydrogen sulphate
8. The correct sequence of reagents for the following
(3) Ethylene conversion will be [JEE (Main)-2017]
(4) Acetylene O HO CH3
5. Arrange the following compounds in order of
decreasing acidity [JEE (Main)-2013]

OH OH OH OH
HO CH3
CHO
; ; ; CH3

Cl CH3 NO2 OCH3 (1) CH3MgBr, [Ag(NH3)2]+OH–, H+/CH3OH

(I) (II) (III) (IV) (2) [Ag(NH3)2]+OH–, CH3MgBr, H+/CH3OH
(1) II > IV > I > III (2) I > II > III > IV (3) [Ag(NH3)2]+OH–, H+/CH3OH, CH3MgBr
(3) III > I > II > IV (4) IV > III > I > II (4) CH3MgBr, H+/CH3OH, [Ag(NH3)2]+OH–

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

9. Phenol on treatment with CO2 in the presence of 12. The products formed in the reaction of cumene with
NaOH followed by acidification produces compound O2 followed by treatment with dil. HCl are
X as the major product. X on treatment with [JEE (Main)-2019]
(CH3CO)2O in the presence of catalytic amount of
H2SO4 produces [JEE (Main)-2018] OH
OH
O
(1) and H3C CH3
O O CH3
O CH3
(1) (2) O CH 3

CO2H
CO2H
(2) and CH 3—OH
O O CH3 CO2H
C
O
OH O
(3) (4)
CO2H (3) and H3C CH3
O CH3
O OH
10. The major product formed in the following reaction O
is
(4) and H3C CH3
O HI
Heat
O 13. Which is the most suitable reagent for the following
[JEE (Main)-2018] transformation? [JEE (Main)-2019]
OH
OH I CH3 CH CH CH2 CH CH3
(1) (2)
OH I CH3 CH CH CH2CO2H

(1) I2/NaOH (2) Alkaline KMnO4

OH I
(3) (4) (3) Tollen’s reagent (4) CrO2Cl2/CS2
I OH 14. The major product of the following reaction is
11. The major product of the following reaction is OH
[JEE (Main)-2019]
Br2(excess)
[JEE (Main)-2019]

SO3H
OH OH
Br Br Br

(1) (2)
(1) (2)
SO3H SO3H
OH OH
Br Br

(3) (4) (3) (4)

Br Br
Br Br
Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
CHEMISTRY ARCHIVE - JEE (Main)

15. The major product obtained in the following (1) PhCOCH2CH3 + CH3MgX
conversion is (2) CH3CH2COCH3+ PhMgX
CH3 O
(3) HCHO+PhCH(CH3)CH2MgX
Br2 (1 eqv.) (4) PhCOCH3+ CH3CH2MgX
O MeOH
18. The major product of the following reaction is
OCH3
O Conc . HBr (excess)

[JEE (Main)-2019] heat

[JEE (Main)-2019]
CH3 O CH3 O CH = CH 2
OH Br
O O OMe (1) (2)
(1) (2)
Br–CHCH 3 Br–CHCH 3
Br Br
O O OH Br
(3) (4)
O CH 3 O
CH3 Br CH 2CH2Br CH 2CH2Br
O Br O
(3) (4) 19. The organic compound that gives following
qualitative analysis is
OMe
O O Test Inference
16. The major product obtained in the following reaction (a) Dil. HCl Insoluble
is
(b) NaOH solution Soluble
O OH (c) Br2/water Decolourization
LiAlH4 [JEE (Main)-2019]
(excess) OH OH
CH3
(1) (2)
NO2 O
[JEE (Main)-2019] NH2 NH2
(3) (4)
OH OH

20. p-Hydroxybenzophenone upon reaction with

bromine in carbon tetrachloride gives
(1) CH3 (2) CH3
[JEE (Main)-2019]
NH2 OH NH2 OH Br O

O OH OH (1)
HO
O

(3) (4) CH3 Br

CH3 (2)
HO
NO2 OH NO2 OH O
Br
OH
(3)
17. CH3 CH2 C CH3 cannot be prepared by HO
O
Ph Br
[JEE (Main)-2019] (4)
HO

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

21. The major product of the following reaction is :

OH
O OH
HI (excess) (1) (2)
'
NC O CH 3
CH3
[JEE (Main)-2019]
OH
I OH O
(1) (2) (3) (4)

NC OH NC I CH3
CH 3

I 24. Consider the following reactions :

OH
(3) (4) Ag2 O
ppt
NC I '
NC OH A
Hg 2+/H+ NaBH4 ZnCl 2 Turbidity
22. The major products of the following reaction are : B C within
conc. HCl 5 minutes
OH
‘A’ is [JEE (Main)-2019]
(1) CHCl 3/aq. NaOH
(1) CH3 – C { CH (2) CH3 – C { C – CH3
(2) HCHO, NaOH (conc.)
(3) H 3O + (3) CH2 = CH2 (4) CH { CH
Cl 25. The increasing order of the pKa values of the
[JEE (Main)-2019] following compounds is
OH
OH OH OH OH
COOH
(1) and Methanol
NO2
NO 2 OMe
Cl
A B C D
OH
[JEE (Main)-2019]
OH (1) D < A < C < B (2) B < C < D < A
(2) and Formic acid
(3) B < C < A < D (4) C < B < A < D
OH 26. 1-methylethylene oxide when treated with an excess
OH of HBr produces: [JEE (Main)-2020]

Br Br
OH (1) (2)
(3) CH3
and Formic acid Br

Cl Br
CH3
(3) Br (4)
OH CH3 Br
COOH
27. In the following reaction sequence, structures of A
(4) and Methanol and B, respectively will be

OH
HBr Na
23. What will be the major product when m-cresol is A (Intramolecular
' Ether
reacted with propargyl bromide (HC { C–CH2Br) in Product) B
presence of K2CO3 in acetone?
CH 2Br
[JEE (Main)-2019]
[JEE (Main)-2020]
Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
CHEMISTRY ARCHIVE - JEE (Main)

Br CH 2Br
(1) A = H3CO OCH3
OH
(1)
&
CH2Br
OCH3
Br Br
B = HO OH
OH
(2)
&
CH 2Br
HO
OH OH

Br
(3)
&
CH 2Br (2) A = HO OH

OH OH

Br HO
(4)
&
CH 2Br B = HO
OH
28. The major product of the following reaction is
H 3C OH
OH dil. H SO
2 4

H 3C
H 3C
[JEE (Main)-2020] (3) A = H3CO OCH3
CH 3

(1)
OCH3
B = HO
OH
H3C OH
CH 3

H3C OH
OH
(2)
H3C OH OH
CH3
OH (4) A = HO OH
H3C OH
(3)
H 3C
HO CH 3 HO

CH3 B = H3CO OCH3

OCH3
(4)
OH
H3C CH 3 30. The major product [B] in the following sequence of
reactions is
29. Among the compounds A and B with molecular
CH3 – C = CH – CH2CH3 (i) B2H6
formula C9H18O3, A is having higher boiling point the [A]
B. The possible structures of A and B are CH(CH3)2 –
(ii) H2O 2, OH
dil. H SO
[JEE (Main)-2020] 
2 4
o[B] [JEE (Main)-2020]
'

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

(1) CH3 – C – CH2CH2CH3 C and D respectively are [JEE (Main)-2020]

C
H3C CH3 OH
(1) C = H3C – CH 2 – CH – CH 3 ;
(2) CH2 = C – CH2CH2CH3
CH(CH3)2 CH3
D = H 3 C – C – OH
(3) CH3 – C = CH–CH2CH3
CH3
CH(CH3)2

(4) CH3 – CH – CH = CH – CH3

(2) C = H3C – CH 2 – CH2 – CH2 – OH;
CH(CH3)2

31. Preparation of Bakelite proceeds via reactions D = H 3C – CH 2 – CH – CH 3

[JEE (Main)-2020] OH

(1) Electrophilic substitution and dehydration

(2) Electrophilic addition and dehydration (3) C = H3C – CH 2 – CH 2 – CH2 – OH;

(3) Nucleophilic addition and dehydration CH 3

(4) Condensation and elimination D = H3C – C – OH
32. The major aromatic product C in the following CH 3
reaction sequence will be

CH 3
(4) C = H 3C – C – OH;
[JEE (Main)-2020] CH 3

OH Br D = H 3C – CH 2 – CH – CH 3

(1) (2) OH

CHO CHO
34. An organic compound ‘A’ (C9H10O) when treated
Br OH with conc. HI undergoes cleavage to yield
(3) (4) compounds ‘B’ and ‘C’. ‘B’ gives yellow precipitate
CO2 H CO2 H with AgNO3 where as ‘C’ tautomerizes to ‘D’. ‘D’
gives positive iodoform test. ‘A’ could be
33. Two compounds A and B with same molecular
formula (C3H6O) undergo Grignard’s reaction with [JEE (Main)-2020]
methylmagnesium bromide to give products C and
D. Products C and D show following chemical
(1) O – CH = CH – CH 3
tests.
Test C D
Ceric O – CH = CH 2
(2) H3C
ammonium Positive Positive
nitrate Test
Turbidity CH 2 – O – CH = CH 2
Turbidity (3)
obtained
Lucas Test obtained
after five
immediately
minutes O – CH 2 – CH = CH 2
(4)
Iodoform Test Positive Negative

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
CHEMISTRY ARCHIVE - JEE (Main)

35. The major product of the following reaction is: (3) H3C CH2 H3C CH3
OH
CH3 conc. HNO3 + conc. and
H 2SO4 H3C CH2

NO 2
CH3
[JEE (Main)-2020] (4) H3C CH3 H3C
OH
and
OH H 3C CH2
H3 C
H 3C
(1) (2) NO2 38. The major product [B] in the following reactions is
O2N NO2
NO 2
CH3
OH
CH3 CH2 CH CH2 OCH2 CH3
OH H 3C NO 2
HI H SO
H 3C NO 2  o [A] alcohol 
2
'
4
o [B]
(3) (4) NO2
Heat

NO2 NO 2 [JEE (Main)-2020]

36. Consider the following reaction : (1) CH3 – CH2 – CH = CH – CH3

OHc CH3
d HO CH3 (2) CH3 CH2 C CH2
OHb OHa
CH3
Chromic (3) CH3 CH C CH3
 o 'P '
anhydride
(4) CH2 = CH2
The product ‘P’ gives positive ceric ammonium
39. The major product [C] of the following reaction
nitrate test. This is because of the presence of
sequence will be
which of these –OH group(s)? [JEE (Main)-2020]
(1) (d) only (i) NaBH 4 DBr
CH2 CH – CHO [A] [B] [C]
(i i) SO Cl2 Anh y.
(2) (c) and (d) AlCl3

(3) (b) only [JEE (Main)-2020]

(4) (b) and (d) Br
37. When neopentyl alcohol is heated with an acid, it
slowly converted into an 85 : 15 mixture of alkenes
(1)
A and B, respectively. What are these alkenes?
D
[JEE (Main)-2020]
Br
(2)
(1) H3C CH3 H 3C CH2 D
and Br
H3 C H 3C
D
(3)
(2) CH3 CH3 CH3 CH2
and D
(4)
CH2 CH3
Br

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

40. Which of the following derivatives of alcohols is [JEE (Main)-2021]

unstable in an aqueous base? [JEE (Main)-2020]
O

(1) RO Me (2) RO—CMe3 (1)

(3) (4) RO
RO O
41. The major product of the following reaction is (2)
HO CH2CH3
H2SO4

O
[JEE (Main)-2020]
(3)
CHCH3 CH2CH3

(1) (2)
O O

CH = CH2 CH2CH3 (4)

(3) (4)
O O 45. Identify Products A and B.

42. A solution of phenol in chloroform when treated with

aqueous NaOH gives compound P as a major dil. KMnO4 CrO3
A B
product. The mass percentage of carbon in P is 273 K
______. (to the nearest integer)
[JEE (Main)-2021]
(Atomic mass : C = 12; H = 1; O = 16)
[JEE (Main)-2020]
43. The increasing order of boiling points of the following (1) A : B:
compounds is OH O

OH OH OH OH

OH
(2) A : B:
OH O
CH3 NO 2 NH 2 OCH3
I II III IV
[JEE (Main)-2020] (3) A : OH B:
(1) III < I < II < IV (2) IV < I < II < III OH O

(3) I < III < IV < II (4) I < IV < III < II
O
44. What is the final product (major) ‘A’ in the given
reaction? (4) A : OHC —

B : HOOC —

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
CHEMISTRY ARCHIVE - JEE (Main)

46. Identify A and B in the chemical reaction. 47. Identify the major products A and B respectively
in the following reactions of phenol:
OCH3 OH
(i) CHCl 3, NaOH Br2 in CS 2
B A
(ii) H 3O
+ 273K
HCl NaI

o [A] o
dry acetone
[B]
(major) major
[JEE (Main)-2021]

OH OH
NO2

(1) and
[JEE (Main)-2021]
Br CHO
OCH3 OCH3
OH OH
Cl I
CHO
(2) and
(1) A = B=
Br

OH OH
NO2 NO 2
Br CHO
(3) and

OCH3 OCH3
Cl OH OH
Br
(4) and
(2) A = B=
CHO
Cl

NO2 NO2 Cl O– Na +

48. +NaOH

OCH3 I
The above reaction requires which of the following
Cl Cl
reaction conditions? [JEE (Main)-2021]
(1) 573 K, 300 atm (2) 623 K, Cu, 300 atm
(3) A = B=
(3) 573 K, Cu, 300 atm (4) 623 K, 300 atm
49. Main Products formed during a reaction of
NO2 NO2 1-methoxy naphthalene with hydroiodic acid are :
[JEE (Main)-2021]

I
OCH3 I
(1) and CH3OH

(4) A = B=
OH

Cl Cl
(2) and CH3OH
NO2 NO2

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

Choose the correct answer from the options given

OH
below [JEE (Main)-2021]
(3) and CH3I (1) (a) and (c) only (2) (a), (b) and (d) only
(3) (b) and (d) only (4) (b), (c) and (d) only
53. The correct options for the products A and B of the
I following reactions are :

(4) and CH3I OH

Br 2 (excess) Br2
A B
50. To synthesise 1.0 mole of 2-methylpropan-2-ol from H2 O CS2 , < 5°C

Ethylethanoate_______equivalents of CH3MgBr
[JEE (Main)-2021]
reagent will be required. (Integer value)
[JEE (Main)-2021] OH OH
Br Br Br
51. An organic compound A (C6H6O) gives dark green (1) A = , B=
colouration with ferric chloride. On treatment with
CHCl3 and KOH, followed by acidification gives Br Br
compound B. Compound B can also be obtained
from compound C on reaction with pyridinium OH OH
chlorochromate (PCC). Identify A, B and C Br Br Br
[JEE (Main)-2021] (2) A = , B=
Br
OH CH2OH OH Br
OH CHO
(1) A = B= C= OH OH
Br Br
(3) A = , B=
CH2OH OH OH
OH CHO Br Br
(2) A = B= C=
OH OH

OH OH (4) A = , B=
OH CHO CH2OH
(3) A = B= C= Br Br

54. Which one of the following phenols does not give

HO CH 2OH OH colour when condensed with phthalic anhydride in
CHO OH presence of conc. H2SO4? [JEE (Main)-2021]
(4) A = B= C=
OH
OH

OH OH
(1) (2)
52.
OH
CH3
Br
(Major product)
OH
The given reaction can occur in the presence of OH OH
(a) Bromine water (b) Br2 in CS2, 273 K
(3) (4)
(c) Br2/FeBr3 (d) Br2 in CHCl3, 273 K

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
CHEMISTRY ARCHIVE - JEE (Main)

55. Given below are two statements: one is labelled as

Assertion (A) and the other is labelled as
Reason (R).
Assertion (A) : Synthesis of ethyl phenyl ether OH
may be achieved by Williamson synthesis.
Reason (R) : Reaction of bromobenzene with
sodium ethoxide yields ethyl phenyl ether. (1) (a) and (b) only (2) (c) only
In the light of the above statement, choose the (3) (a), (b) and (c) (4) (b) only
most appropriate answer from the options given
58. The major product formed in the following reaction
below: [JEE (Main)-2021]
is :
(1) (A) is not correct but (R) is correct CH3
(2) (A) is correct but (R) is not correct conc. H2SO 4
CH3 C CH CH3
a few drops
(3) Both (A) and (R) correct but (R) is NOT the CH3 OH
correct explanation of (A) [JEE (Main)-2021]
(4) Both (A) and (R) are correct and (R) is the
correct explanation of (A) CH 3 CH3

56. The major product of the following reaction, if it (1)

occurs by SN2 mechanism is : H 3C CH3

OH
CH 3
K2CO3
+ Br (2) CH 3 CH2
acetone C CH
CH 3
[JEE (Main)-2021]
CH 3
C CH CH 3
O O (3)
CH3
(1) (2)

(4) CH3 C CH CH2CH 3

O CH 3
O
O
(3) (4) 59. Which of the following reagents/reactions will
convert ‘A’ to ‘B’?

57. The compound/s which will show significant

intermolecular H-bonding is/are [JEE (Main)-2021]
NO2
H
OH N CH3 [JEE (Main)-2022]

O (1) PCC oxidation

HO (2) Ozonolysis
(3) BH3, H2O2/–OH followed by PCC oxidation
(a) (b)
(4) HBr, hydrolysis followed by oxidation by
K2Cr2O7.

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

60. The major product in the reaction

(1)
is:

[JEE (Main)-2022]
(1) t-Butyl ethyl ether (2)
(2) 2, 2-Dimethyl butane
(3) 2-Methyl pent-1-ene
(4) 2-Methyl prop-1-ene
(3)
61. The intermediate X, in the reaction :

(4)

63. Compound ‘P’ on nitration with dil. HNO3 yields

two isomers (A) and (B) show the intramolecular
is :
and intermolecular hydrogen bonding respectively.
Compound (P) on reaction with conc. HNO3 yields
a yellow compound ‘C’, a strong acid. The number
of oxygen atoms is present in compound ‘C’
[JEE (Main)-2022] _____. [JEE (Main)-2022]

64. Match List I with List II.

List I List II
(1) (2)
OH OH
A. CHO I. Br2 in CS2

OH
(3) (4) B. II. Na2Cr2O7/ H2SO4

62. In the following reaction: OH o

C. III. Zn
o

OH OH

D. IV. CHCl3/NaOH
The compound A and B respectively are:
Br
[JEE (Main)-2022]

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
CHEMISTRY ARCHIVE - JEE (Main)

Choose the correct answer from the options given 68. Most stable product of the following reaction is:
below: [JEE (Main)-2022]
(1) A-IV, B-III, C-II, D-I (2) A-IV, B-III, C-I, D-II
(3) A-II, B-III, C-I, D-IV (4) A-IV, B-II, C-III, D-I

65. The major product (P) of the given reaction is

(where, Me is –CH3) [JEE (Main)-2022]

(1) (2)

[JEE (Main)-2022]

(3) (4)
(1) (2)

69. Given below are two statements:

Statement I: On heating with KHSO4, glycerol is

(3) (4) dehydrated and acrolein is formed.

Statement II: Acrolein has fruity odour and can be

66. Given below are two statements.
used to test glycerol’s presence.
Statement I : Phenols are weakly acidic.
Choose the correct option.
Statement II : Therefore they are freely soluble in [JEE (Main)-2022]
NaOH solution and are weaker acids than alcohols (1) Both Statement I and Statement II are
and water. correct.

Choose the most appropriate option. (2) Both Statement I and Statement II are
incorrect.
[JEE (Main)-2022]
(3) Statement I is correct but Statement II is
(1) Both Statement I and Statement II are correct. incorrect.
(2) Both Statement I and Statement II are correct. (4) Statement I is incorrect but Statement II is
(4) Statement I is correct but Statement II is correct.
incorrect.
(4) Statement I is incorrect but Statement II is 70. Arrange the following in decreasing acidic strength
correct.

67. In the given reaction,

[JEE (Main)-2022]
the number of sp 2 hybridised carbon(s) in (1) A > B > C > D (2) B > A > C > D
compound 'X' is _____. [JEE (Main)-2022] (3) D > C > A > B (4) D > C > B > A

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

71. A sample of 4.5 mg of an unknown monohydric 76. A 100 mL solution of CH3CH2MgBr on treatment
alcohol, R–OH was added to methylmagnesium with methanol produces 2.24 mL of a gas at STP.
iodide. A gas is evolved and is collected and its The weight of gas produced is_____ mg. [nearest
volume measured to be 3.1 mL. The molecular integer]
weight of the unknown alcohol is___ g/mol. [JEE (Main)-2022]
[Nearest integer] [JEE (Main)-2022]
77. In the following reaction,
72. The difference in the reaction of phenol with
bromine in chloroform and bromine in water
medium is due to: [JEE (Main)-2022]
(1) Hyperconjugation in substrate
(2) Polarity of solvent
(3) Free radical formation
(4) Electromeric effect of substrate
73. The major product of the following reaction is
the % yield for reaction I is 60% and that of
reaction II is 50%. The overall yield of the complete
reaction is _______%. [Nearest integer]
[JEE (Main)-2022]

[JEE (Main)-2022] 78. An organic compound ‘A’ contains nitrogen and

chlorine. It dissolves readily in water to give a
solution that turns litmus red. Titration of
compound ‘A’ with standard base indicates that
(1) (2) the molecular weight of ‘A’ is 131±2. When a
sample of ‘A’ is treated with aq. NaOH, a liquid
separates which contains N but not Cl. Treatment
of the obtained liquid with nitrous acid followed by
phenol gives orange precipitate. The compound A
is :
(3) (4)
[JEE (Main)-2022]

74. Hydrolysis of which compound will give carbolic

acid? [JEE (Main)-2022]
(1) Cumene
(1) (2)
(2) Benzenediazonium chloride
(3) Benzal chloride
(4) Ethylene glycol ketal
75. The number of non-ionisable protons present in the
product B obtained from the following reactions
is_____.
(3) (4)
C2H5 OH  PCI3 o C2H5 Cl  A
A  PCl3 o B

[JEE (Main)-2022]

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
CHEMISTRY ARCHIVE - JEE (Main)

79. Identify the major products A and B for the below 80. The major product in the given reaction is
given reaction sequence.

(1)H ,heat

(2)HBr
o

[JEE (Main)-2022]

(1) (2)
[JEE (Main)-2022]

(3) (4)

81. Compound I is heated with Conc. HI to give a

(1)
hydroxy compound A which is further heated with
Zn dust to give compound B. Identify A and B.

[JEE (Main)-2022]
(2)

(1)

(2)
(3)

(3)

(4)

(4)

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

82. A compound ‘X’ is acidic and it is soluble in NaOH 84. A 1.84 mg sample of polyhydric alcoholic compound
‘X’ of molar mass 92.0 g/mol gave 1.344 mL of H2
solution, but insoluble in NaHCO 3 solution.
gas at STP. The number of alcoholic hydrogens
Compound ‘X’ also gives violet colour with neutral present in compound ‘X’ is____.
FeCl3 solution. The compound ‘X’ is :
[JEE (Main)-2022]
[JEE (Main)-2022]
85. The major product formed in the following reaction,
is

(1) (2) +
H
OH +
O
[JEE (Main)-2022]

(3) (4)
(1)

83. When ethanol is heated with conc. H2SO4, a gas

(2)
is produced. The compound formed, when this gas
is treated with cold dilute aqueous solution of
Baeyer’s reagent, is (3)
[JEE (Main)-2022]
(1) Formaldehyde (2) Formic acid
(3) Glycol (4) Ethanoic acid? (4)

‰‰‰

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
Chapter 25

Alcohols, Phenols and Ethers

1. Answer (2) due to –I effect of Cl group, p-cresol due to +I and
+H effects of CH3 group which destabilises its
OH OH conjugate base. p-methoxphenol is least acidic due
COOH to +R effect of OCH3 group.
CO2
NaOH 6. Answer (2)
Tertiary alcohol gives instant turbidity with Lucas
Salicylic acid
reagent and the reaction follows SN1 mechanism
2. Answer (3) due to stability of tertiary carbocation.

Alcohols which give more stable carbocation is 7. Answer (1)

more reactive with Lucas reagent —
O O O
(Anhy. ZnCl2 + conc. HCl) H O—
— O=C=O
C
OH O
| †
Anhy. ZnClHCl
CH3  C  CH2  CH3  o CH3  C  CH2CH3
| | OH OH
—
CH3 CH3 COOH COO
+
More reactive More stable tertiary (CH3CO)2O H
carbocation

(B)
3. Answer (3)
D>C>A>B OCOCH3
COOH

OH OH OH OH
(C)
> > >
NO2 8. Answer (3)
NO2 –I I CH3
–R, –I Unsubstituted +R, H
O O
Order of acidic strength = –R > –I > I > + H > +R
[Ag(NH3)2]+OH– CH3 – OH/H+
4. Answer (4) Esterification
100°C-110°C
C2H5HSO4
C=O C=O
140°C H HO
C2H5OH + H2SO4 C2H5OC2H5
180°C
CH2 = CH2 O (i) CH3MgBr HO CH3
5. Answer (3) (3 moles)
(ii) H2O
The acidic strength of the given derivatives of
phenol is decided by the stability of their conjugate
bases. p-nitrophenol is most acidic as –I and –R CH3
C – OCH3 HO – C
effects of NO2 group stabilises its conjugate base O CH3
most effectively. This is followed by p-chlorophenol

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

9. Answer (1) 14. Answer (3)

OH OH
OH OH
Br Br
COOH Br2
CO2, NaOH
excess
Acidification

(Major) SO3H Br
O
OH O–C–CH3 15. Answer (2)
COOH COOH
(CH3CO)2O
H2SO4 CH3 O

Acetyl salicylic acid

O OCOCH 3
(Aspirin)
Br2 Br
+

10. Answer (4)

O O
CH 3
O HI I MeOH
Heat
+ I
O
O OH O
+ OMe
OH
11. Answer (1) Br
O

16. Answer (1)

Br OH +
aqKOH CrO3/H
O OH OH
Br Br
LiAlH4
(excess)
C=O O
CH3
OH
H2SO4
' NO2 O NH2 OH
Br Br
12. Answer (4) 17. Answer (3)
O—O—H OH
O
CH3—CH—CH3 OH
CH 3—C—CH3 1. CH3MgX
1. Ph C CH2CH3 Ph C CH2 CH 3
O 2. H3O+
O2 H+ ||
+ CH3—C—CH3 CH3

Cumene Cumene
peroxide O OH

13. Answer (1) 1. PhMgX

CH3CH2 C CH3
2. CH3 CH2 C CH3
2. H3 O
+

CH3 – CH = CH – CH 2 – CH – CH 3
Ph
OH
I2/NaOH O

CH3 – CH = CH – CH 2 – C – CH 3 3. H C H + PhCH(CH3)CH2MgX
O
H3 O+
I2/NaOH HOCH2 CH 2 CH Ph
CH3 – CH = CH – CH 2 – C – ONa + CHI 3
CH3
O

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
CHEMISTRY ARCHIVE - JEE (Main)

22. Answer (3)

O OH
1. CH3CH2 MgX
4. Ph C CH3 Ph C CH3
2. H3O+
CH2 CH3 OH OH
CHO
Reaction (3) gives primary alcohol which is different CHCl 3
from tertiary alcohol given by the remaining NaOH
reactions.
18. Answer (1) Cl Cl
HCHO, conc NaOH
OCH3 OCH3 OH
HBr HBr + CH3Br
excess
OH
CH —
— CH 2 CH — CH 3 CH — CH 3
CH2OH
+ HCOO
Br Br

19. Answer (2) Cl

+
H3O
OH HCl
No reaction
O
–
OH
NaOH
OH
+ HCOOH
OH
Br2
Br Br
H2 O Cl

Br 23. Answer (3)

–
20. Answer (4) OH O O

K2CO3 HC{ C–CH2 –Br

O O in SN2
Br2 /CCl4 H3C acetone CH3 H3C
C OH C OH
Meta cresol is neutralised by K 2 CO 3 . The
Br phenoxide ion attacks at the C-atom carrying
–M group +M group Br-atom to give ether following SN2 mechanism.
24. Answer (1)
Product will formed as per –OH group (+M group)
21. Answer (3)
CH3 C CH
H
HgSO4 + H2SO4
O O+
CH3 2 HI CH 3 –
+2I
OH O
tautomerise
CH CH CH3 C CH CH3 C CH3
+
NC O NC O
H NaBH4

OH OH
+ CH 3I + CH3 – CH – CH3 ZnCl2 + HCl
ppt. (in 5 min) CH3 CH CH3
I (Lucas reagent)
CH (confirmation
NC OH
of 2° alcohol)

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

25. Answer (3) 29. Answer (4)

Acidic strength In (A), Intermolecular H-bonding is possible while
in (B) there is no inter-molecular H-bonding. So A
OH OH OH OH
is having higher boiling point than B.
> > > 30. Answer (1)
NO2
NO 2 OMe CH3 – C = CH – CH2 – CH3
(i) B2H6
(B) (C) (A) (D) CH (ii) H2O2, OH–
? pKa : B < C < A < D CH3 CH3
26. Answer (3)
OH
H
+
CH3 – CH – CH – CH2 – CH3
+
O O CH
CH3 CH3
H
(A)
–
Br
dil H2SO4, '

OH CH3 CH3
C=C
Br CH3 CH2 – CH 2 – CH3
(B)
HBr
31. Answer (1)
Br Formation of Bakelite
Br Electrophilic substitution reaction of phenol with
27. Answer (4) formaldehyde followed by dehydration
32. Answer (1)

H
O O Br O OH
HBr (excess)
'
Br
HBr
'
CH2–Br CH2–Br Br
alc. KOH

OH OH
O3
OH HO +
Zn/H3O
Na Br C == O
Ether H
CH2Br
+ O C C O
+ HCHO
28. Answer (4) H H

dil H2 SO4
33. Answer (1)
OH – H2O +
CH2
OH
|
CH3 —CH2 —CH—CH3 can give positive CAN
H2 O
–H+ test, iodoform test, and with Lucas reagent it
takes 5 minutes to give turbidity.
+ OH

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
CHEMISTRY ARCHIVE - JEE (Main)

37. Answer (4)

CH
3
|
CH3 —C — OH cannot give iodoform test OH +
H
| '
CH3
Neopentyl
but can give CAN test and Lucas test. alcohol
34. Answer (3)

CH2 O CH CH2

HI (major) (minor)

CH2 I + CH2 CH OH 38. Answer (3)

Tautomerise CH3
can give yellow HI
CH3 CHO H3C—CH2—CH—CH2—O—CH2—CH3
ppt with AgI Heat
can give iodoform
test
CH3

35. Answer (2) CH3—CH2—CH—CH2—OH + CH3CH2 – I

[A]
H2SO4/'
OH OH
H3C conc. HNO3 H3C CH3
+
conc. H2SO4 CH3—CH==C—CH3
NO2 NO2
NO2
39. Answer (3) (i) NaBH4
CH2 CH CHO H 2C CH CH2OH
Position of electrophilic attack is directed by the
electron donating group present in ring (ii) SOCl2

H 2C CH CH2 Cl
36. Answer (4) [A]
Br
OHc DBr D
H2C CH CH2Cl Anhy
d HO [A] AlCl3
OHb [B] [C]
OHa
40. Answer (1)
Chromic anhydride

O O – O
OH /H2O
d HO ROH +
OHb Hydrolysis
O RO Me Me O
Ester
n
So, Ester is unstable in an aqueous basic solution
and undergoes hydrolysis to give alcohol and
Hb and Hd can give CAN test carboxylate.

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

41. Answer (4)

dil. KMnO4 CrO 3
–
OH OH
OH , H 2O +
H (Jones
CH2CH3 273 K OH O
HO CH2 CH3 reagent)

+ H
H 3°–alcohols do not undergo oxidation reaction
–H2O
easily.
O O
46. Answer (1)

CH2 CH3
OCH3 OCH3 OCH3

+ – Cl
O † –
HCl Cl

H H
42. Answer (69.00)
NO2 NO2 NO 2
OH OH NaI/acetone

CHO
NaOH OCH3
+ CHCl 3
I
P(salicylaldehyde)

12 u 7 NO2
? mass % of C in P = u 100
84  6  32
= 68.85%
Correct option should be (1)
| 69%
47. Answer (2)
43. Answer (None) Bonus
Order of boiling point of the following compound is
I < IV < II < III OH OH
I o B.P 202°C Br2/CS2
II o B.P. 279°C 273 K

III o B.P. 284°C Br

Major
IV o B.P. 243°C
A
44. Answer (4)
OH OH
(i) CHCl 3,NaOH
CHO
+
.. + (ii) H 3O
OH Major
..

+
+ B
H
H

So option (2) is the correct answer

1, 2-hydride 48. Answer (4)
shift
Chlorobenzene is fused with NaOH at 623 K and
300 atmospheric pressure to get sodium
+ phenoxide.

Cl O –Na +
(5 hyperconjugation
and 3°-carbocation) 623 K
+NaOH
300 atm

45. Answer (3)Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
CHEMISTRY ARCHIVE - JEE (Main)

49. Answer (3) 53. Answer (3)

OCH3 OH OH OH
Br Br
Br 2 + H2O
HI
+ CH3I

Br
H
(A)
+O CH3 OH
OH OH
–
I
+ CH3I Br 2
CS2

50. Answer (2) Br

(B)

54. Answer (2)

OH
2-methylpropan-2-ol OH OH

O O OH
O MgBr Conc. H 2SO4
2eq. CH MgBr

3
o O + O
OEt
CH3
O O
CH 3
Phthalic anhydride Phenolphthalein
†
H 3O As phthalic anhydride being bulky, electrophilic
substitution reaction occurs at para position in
OH phenol or its derivatives
OH

51. Answer (3)

CH 3
OH OH Does not condense with phthalic anhydride because
CHO para position is blocked.
1. CHCl3 + KOH
2. H
+
55. Answer (2)
(A) (B) Assertion is correct

(Reimer-Tiemann Reaction)
–
OH OH
O Na+ + CH 3–CH2 – X
CH 2–OH CHO
PCC
O–CH 2–CH3 + NaX

(C) (B) But the reason is not correct because aryl halides
do not undergo nucleophilic substitution reactions.
52. Answer (4)
56. Answer (2)
OH OH
OH O– O
Br2 Br
K2CO3
CS2 or CHCl3, 273 K SN 2
or
Br2/FeBr3 (Attack is on least
Br hindered position)

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

57. Answer (4) 60. Answer (4)

O + O–
N H
O
(a)

Intramolecular
H-bonding

NH CH 3 Intramolecular
(b) C H-bonding
is not possible 61. Answer (3)
O here. So,
HO
intermolecular
H-bonding is
prominent

Because of large steric

crowding, intermolecular
H-bonding is difficult
OH

58. Answer (1)

CH 3 CH3
conc. H2SO 4
CH 3 C CH CH3 CH3 C CH CH3
+
CH 3 OH CH3
62. Answer (3)
+
H 1, 2-methyl shift

CH 3
H
H3C CH 3 +
+
C C H
CH3 C C CH 3
H3C CH 3
CH3 CH3

59. Answer (3) 63. Answer (7)

The first step involves addition of H2O to alkene

according to anti-markownikoff’s rule while the
second step involves oxidation of 1° alcohol to
aldehyde.
The number of oxygen atoms = 7

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
CHEMISTRY ARCHIVE - JEE (Main)

64. Answer (1) 66. Answer (1)

pKa 10

Alcohol pKa | 16
H2O pKa | 15
67. Answer (8)

68. Answer (2)

?Correct match is

(A) - IV, (B) - III, (C) - II, (D) - I

65. Answer (3)
? Option (2) is correct option.
69. Answer (3)
Glycerol, on heating with KHSO 4 , undergoes
dehydration to give unsaturated aldehyde called
acrolein. So, statement I is correct.

Acrolein has piercing unpleasant smell. So,

statement-II is incorrect.
70. Answer (1)

NO2

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
ARCHIVE - JEE (Main) CHEMISTRY

71. Answer (33) 75. Answer (02.00)

R – OH + CH3 MgI Ÿ R – OMgI + CH4 PCl3 + C2H5OH o C2H5Cl + H3PO3
moles of alcohol (ROH) {moles of CH4 (A)
At STP, [Assuming STP] H3PO3 + PCl3 o H4P2O5

1 mole corresponds to 22.7 L (A) (B)

3.1 Structure of H4P2O5

Hence, 3.1 mL { mol
22700

3.1
So, moles of alcohol =
22700

3.1 4.5 u 10 –3
Ÿ
22700 M Total 2 non-ionizable protons are present
M  33 g/mol 76. Answer (03.00)
72. Answer (2)
CH 3 – CH 2 – MgBr + CH 3 OH o CH 3 – CH 3 +
Phenol gives different products with bromine in
MgBr(OCH3 )
chloroform and water medium due to the polarity
difference between chloroform and water acting as As 2.24 ml is formed at STP.
solvent Number of moles of ethane gas produced
73. Answer (1)
2.24X
= 10–4 ml
22.4

Mass of ethane produced = 10–4 × 30

= 3 × 10– = 3 mg
77. Answer (30)

(When G = EDG) (When G = EWG)

EDG o Electron donating group

EWG o Electron withdrawing group The % yield of the complete reaction is

74. Answer (2) Ÿ 0.6 × 0.5 × 100 = 30%
Phenol, is known as Carbolic acid. 78. Answer (4)
Diazonium salt are hydrolysed to phonols.

is acidic in nature as it can undergo

cationic (A) hydrolysis in aqueous solution.

Benzal chloride on hydrolysis gives benzaldehyde

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
CHEMISTRY ARCHIVE - JEE (Main)

82. Answer (2)

79. Answer (2)

83. Answer (3)

84. Answer (6)

Moles of H2 produced at STP

1.344 u 10 –3
= 6 × 10–5 mole
22.4
? Moles of hydrogen atom produced

80. Answer (3) = 12 × 10–5 mol

Moles of organic compound

1.84 u 10 –3
= 2 × 10–5
92
? Number of alcoholic hydrogen present

12 u 10 –5
6
81. Answer (4) 2 u 10 –5
85. Answer (4)

‰‰‰

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456