CBSE Class 12 Chemistry 2017 Outside Delhi Set 1 Solved Paper

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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:
CH2=CH2
H3O+
CH3
+
C
H2
+H2O

OR
Write the structures of the products when Butan-2ol reacts with the following :
(a) CrO3
(b) SOCI2
Solution:  
(a) Increasing order of acidic strength:
p-nitrophenol in most acidic due to presence of NO2 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 CH3 group i.e., electron releasing group (+ I group) which destablises phenoxide ion so decreases acidity.
(b) Mechanism:
(i) Electrophilic attack of H3O+
H2O+H+(From acid) H3O+

(ii) Nucleophilic attack of water on carbocation.

(iii) Deprotonation:

OR
(a) When Butan-2-ol reacts with CrO3, it forms butan-2-one.
CH3
CH
|
OH
CH2
CH3
CrO3
CH3
C
O
CH2
CH3
Butan2one
+H2O

(b) Butan-2-ol reacts with /SOCl2 to form 2-chlorobutane.
H
H
|
C
|
H
H
|
C
|
OH
H
|
C
|
H
H
|
C
|
H
H
+SOCl2
H
H
|
C
|
H
H
|
C
|
Cl
H
|
C
|
H
H
|
C
|
H
H
2Chlorobutane
+SO2
+HCl
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