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Question : 6
Total: 26
(a) Arrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenol.
(b) Write the mechanism (using curved arrow notation) of the following reaction:
CH 2 = CH 2
CH 3 −
H 2 + H 2 O
OR
Write the structures of the products when Butan-2ol reacts with the following :
(a)CrO 3
(b)SOCI 2
(b) Write the mechanism (using curved arrow notation) of the following reaction:
OR
Write the structures of the products when Butan-2ol reacts with the following :
(a)
(b)
Solution:
(a) Increasing order of acidic strength:
− NO 2 group i.e., electron with drawing group (-I group) which stabilises phenoxide ion so increases acidity while p-serve is least acidic due to presence of − CH 3 group i.e., electron releasing group (+ I group) which destablises phenoxide ion so decreases acidity.
(b) Mechanism:
(i) Electrophilic attack ofH 3 O +
H 2 O + H + (From acid) → H 3 O +
(ii) Nucleophilic attack of water on carbocation.
(iii) Deprotonation:
OR
(a) When Butan-2-ol reacts withCrO 3 , it forms butan-2-one.
CH 3 −
− CH 2 − CH 3
+ H 2 O
(b) Butan-2-ol reacts with/ S O C l 2 to form 2-chlorobutane.
H −
−
−
−
− H + SOCl 2 →
+ SO 2 + HCl
p-nitrophenol in most acidic due to presence of
(b) Mechanism:
(i) Electrophilic attack of
(ii) Nucleophilic attack of water on carbocation.
(iii) Deprotonation:
OR
(a) When Butan-2-ol reacts with
(b) Butan-2-ol reacts with
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