Chapter 23

Alcohols, Phenols and Ethers

Only One Option Correct Type Questions

HBr
1. In the reaction OCH3 the products are [IIT-JEE-2010 (Paper-1)]

(A) Br OCH3 and H2 (B) Br and CH3Br

(C) Br and CH3OH (D) OH and CH3Br

2. The carboxyl functional group (–COOH) is present in [IIT-JEE-2012 (Paper-1)]

(A) Picric acid (B) Barbituric acid
(C) Ascorbic acid (D) Aspirin
3. The acidic hydrolysis of ether (X) shown below is fastest when [JEE (Adv)-2014 (Paper-2)]

Acid
OR OH + ROH

(A) One phenyl group is replaced by a methyl group

(B) One phenyl group is replaced by a para-methoxyphenyl group
(C) Two phenyl groups are replaced by two para-methoxyphenyl groups
(D) No structural change is made to X
4. Newman projections P, Q, R and S are shown below:

OH
CH3 H3C CH 3 CH 3
CH3
H C2H 5 H C2H5 CH(CH 3)2
HO CH 3 H

C2 H5 HO CH 3 H H
H3C C 2H5 H
CH3 CH 3 C2 H5 OH
Q R S
P
Which one of the following options represents identical molecules? [JEE (Adv)-2020 (Paper-1)]
(A) P and Q (B) Q and S
(C) Q and R (D) R and S

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One or More Option(s) Correct Type Questions

OH

5. In the reaction NaOH(aq)/Br2 the intermediate(s) is/are [IIT-JEE-2010 (Paper-1)]

O O
Br
(A) (B)

Br Br
Br
O O

(C) (D)
Br
Br
6. The major product(s) of the following reaction is(are) [JEE (Adv)-2013 (Paper-2)]
OH

aqueous Br2 (3.0 equivalents)

?

SO3H
OH OH OH OH
Br Br Br Br Br

Br Br Br Br Br
SO3H Br Br SO3H
P Q R S
(A) P (B) Q
(C) R (D) S

7. In the following reaction, the product(s) formed is(are) [JEE (Adv)-2013 (Paper-2)]

OH

CHCl3
OH
– ?

CH3

OH O OH OH
OHC CHO CHO

CH3 H3C CHCl2 H3C CHCl2 CH3

P Q R S
(A) P (major) (B) Q (minor)
(C) R (minor) (D) S (major)
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8. The reactivity of compound Z with different halogens under appropriate conditions is given below :
[JEE (Adv)-2014 (Paper-1)]

OH mono halo substituted

derivative when X2 = I2
X2
di halo substituted
derivative when X2 = Br2
C(CH3)3
Z
tri halo substituted
derivative when X2 = Cl2
The observed pattern of electrophilic substitution can be explained by
(A) The steric effect of the halogen (B) The steric effect of the tert-butyl group
(C) The electronic effect of the phenolic group (D) The electronic effect of the tert-butyl group
9. The major product U in the following reactions is [JEE (Adv)-2015 (Paper-2)]

+
radical,
CH2=CH–CH3, H initiator, O2
T U
high pressure, heat
H

O
O H3C CH3
CH3 O
O H
(A) (B)

O
O CH2
CH2 O H
O
(C) (D)

10. The correct statement(s) about the following reaction sequence is(are) [JEE (Adv)-2016 (Paper-1)]
(i) O CHCl /NaOH
Cumene(C9H12 ) 
2  P 

3 Q(major)  R(minor)
(ii) H3O

NaOH
Q 
S
PhCH2Br

(A) R is steam volatile

(B) Q gives dark violet coloration with 1% aqueous FeCl3 solution
(C) S gives yellow precipitate with 2,4-dinitro-phenylhydrazine
(D) S gives dark violet coloration with 1% aqueous FeCl3 solution

11. In the following reaction sequence, the correct structure(s) of X is (are) [JEE (Adv)-2018 (Paper-1)]

(1) PBr3, Et2O Me N3

X
(2) Nal, Me2CO
(3) NaN3, HCONMe2
enantiomerically
pure

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Me OH Me OH
(A) (B)

(C) Me (D)
OH Me OH

12. Choose the correct option(s) for the following set of reactions [JEE (Adv)-2019 (Paper-1)]

(i) MeMgBr conc. HCl

C6H 10O Q S
(ii) H2 O
(major)
20% H3 PO 4, 360 K

(i) H2, Ni HBr, benzoyl peroxide

T R  U
(ii) Br 2 , h 
(major) (major) (major)

CH3 CH3
H 3C Br H3C Br
Cl Cl
(A) (B)

S T U S

CH3 CH3
H 3C Br H 3C Cl
Br Br
(C) (D)
U T S U

Matrix-Match / Matrix Based Type Questions

13. Match the compounds in Column I with their characteristic test(s)/reaction(s) given in Column II.
[IIT-JEE-2008 (Paper-2)]
Column I Column II

(A) H2N—NH3Cl (p) Sodium fusion extract of the compound gives Prussian
blue colour with FeSO4


NH3l
(B) HO (q) Gives positive FeCI3 test
COOH


(C) HO NH3Cl (r) Gives white precipitate with AgNO3


(D) O2N NH—NH3Br (s) Reacts with aldehydes to form the corresponding

NO2 hydrazone derivative

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14. Match the compounds in LIST-I with the observations in LIST-II, and choose the correct option.
[JEE (Adv)-2022 (Paper-1)]
LIST-I LIST-II

(I) Aniline (P) Sodium fusion extract of the compound on boiling with
FeSO4, followed by acidification with conc. H2SO4, gives
Prussian blue color.

(II) o-Cresol (Q) Sodium fusion extract of the compound on treatment

with sodium nitroprusside gives blood red color.

(III) Cysteine (R) Addition of the compound to a saturated solution of

NaHCO3 results in effervescence.

(IV) Caprolactam (S) The compound reacts with bromine water to give a white
precipitate.

(T) Treating the compound with neutral FeCl3 solution

produces violet color.

(A) I  P, Q; II  S; III  Q, R; IV  P

(B) I  P; II  R, S; III  R; IV  Q, S

(C) I  Q, S; II  P, T; III  P; IV  S

(D) I  P, S; II  T; III  Q, R; IV  P

Integer / Numerical Value Type Questions

15. Total number of isomers, considering both structural and stereoisomers, of cyclic ethers with the molecular formula
C4H8O is ____ [JEE (Adv)-2019 (Paper-2)]
16. An organic compound (C8H10O2) rotates plane-polarized light. It produces pink color with neutral FeCl3 solution.
What is the total number of all the possible isomers for this compound? [JEE (Adv)-2020 (Paper-2)]
17. Consider the following reaction. [JEE (Adv)-2022 (Paper-1)]

On estimation of bromine in 1.00 g of R using Carius method, the amount of AgBr formed (in g) is ____.

[Given: Atomic mass of H = 1, C = 12, O = 16, P = 31, Br = 80, Ag = 108]

18. The weight percentage of hydrogen in Q, formed in the following reaction sequence, is ________.
[JEE (Adv)-2022 (Paper-1)]

[Given: Atomic mass of H = 1, C = 12, N = 14, O = 16, S = 32, Cl = 35]

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19. If the reaction sequence given below is carried out with 15 moles of acetylene, the amount of the product D
formed (in g) is __________. [JEE (Adv)-2022 (Paper-1)]

The yields of A, B, C and D are given in parentheses.

[Given: Atomic mass of H = 1, C = 12, O = 16, Cl = 35]
  

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