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 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions

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ORGANIC CHEMISTRY
ALCOHOL, PHENOL & ETHER
1. In the following reaction sequence, the correct structure(s) of X is (are) [JEE(Advanced) 2018]

X  →
3 21) PBr , Et O
2) Nal, Me2 CO
3) NaN3 ,HCONMe2

Me OH
(A) (B)

(C) (D)
Me OH
2. The correct statements(s) about of the following reaction sequence is(are) [JEE(Advanced) 2016]
(i) O22 CHCl
CHCl33/NaOH
/NaOH
Cumene(C99H
H1212)) ++ P Q (major) + R (minor)
(ii) H
H33O
NaOH
Q S
PhCH22Br
PhCH Br
(A) R is steam volatile
(B) Q gives dark violet coloration with 1% aqueous FeCl3 solution
(C) S gives yellow precipitate with 2, 4,-dinitrophenylhydrazine
(D) S gives dark violet coloration with 1% aqueous FeCl3 solution
3. The number of hydroxyl group(s) in Q is [JEE(Advanced) 2015]
+ aqueous dilute KMnO
KMNO44 (excess)
H H+
H
P Q
heat 0°C
HO
H
H33C
C CH
CH33

4. The acidic hydrolysis of ether (X) shown below is fastest when [JEE(Advanced) 2014]

acid
OR OH + ROH

[X]
(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 group
(D) no structural change is made to X

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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®
SOLUTIONS
1. Ans. (B)

(1)PBr3 Et 2 O
Sol. X →
(2)NaI, Me 2 C = O
(3)NaN3 , HCONMe 2

all the three reaction are SN2 so X is

2. Ans. (B, C)

CH
CH33 CH33
Sol. O22
CH C–O–OH (Cumene hydroperoxide)
CH
CH33 CH33 +
∆
H+//∆
H
OH O
+ H33C–C–CH
C–C–CH33
(Acetone)
(phenol)
P

OH OH OH
CH=O
CHCl33
+NaOH +

(P)
Q CH=O High boiling point due to
(major) R inter molecular H-bonding
Steam volatile (minor) So R is not steam volatile
(forms intramolecular
hydrogen bonding)

OH OCH2Ph
CH=O CH=O
NaOH
PhCH22Br
PhCH Br
S
(does not give dark violet
coloration with 1% FeCl33 solution)

Q gives dark violet coloration with 1% aqueous FeCl3 solution because it has phenolic (–OH) group.

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 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
®
3. Ans. (4)
Sol. +
OH
H dil. KMnO4

HO H3C OH
H3C
H3C CH3 CH3 HO OH
CH3

Mechanism :
+
H –H2O
+ +
HO H2O
H3C CH3 H3C CH3 H3C CH3

OH
+
–H dil. KMnO4
HO OH
H3C + H3C
H3C CH3
CH3 CH3 OH
(Major product)

4. Ans. (C)

Sol. Ph H
H+ RDS + Ph
OR Ph C – O – R Ph – C + ROH
+
Ph
Ph

H2O
Ph Ph H
+ ⊕
H3O + Ph C—OH Ph – C—O
Ph Ph H
H2O

If 2 Ph groups are substituted by 2 MeO groups then carbocation formed in above sequence is

more stable and rate of above hydrolysis increases.