Tertiary butyl bromide on reaction with alcoholic ammonia gives
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a) i) The equations for the steps in S
N
1
mechanism of the conversion of tert.butylbromide into tertbutylalcohol are given below.
(CH
3
)
3
C−Br→(CH
3
)
3
C
+
+Br
−
(CH
3
)
3
C
+
+OH
−
→(CH
3
)
3
CBr
ii) Haloarenes are less reactive towards nucleophilic substitution reactions than Haloalkanes. Give a reason. In haloarenes, the C−X bond has partial double bond character as the lone pair of electrons on halogen is in resonance with benzene ring. Hence, C−X bond is difficult to break in haloarenes. In haloalkanes, C−X bond is single bond and is easy to break.
b) The completed equations equations are given below.
i) C
2
H
5
OH+SOCl
2
→C
2
H
5
−Cl+SO
2
↓+HCl↓
ii) 2C
6
H
5
−Cl+2Na
ether
C
6
H
5
−C
6
H
5
+2NaCl
N
1
mechanism of the conversion of tert.butylbromide into tertbutylalcohol are given below.
(CH
3
)
3
C−Br→(CH
3
)
3
C
+
+Br
−
(CH
3
)
3
C
+
+OH
−
→(CH
3
)
3
CBr
ii) Haloarenes are less reactive towards nucleophilic substitution reactions than Haloalkanes. Give a reason. In haloarenes, the C−X bond has partial double bond character as the lone pair of electrons on halogen is in resonance with benzene ring. Hence, C−X bond is difficult to break in haloarenes. In haloalkanes, C−X bond is single bond and is easy to break.
b) The completed equations equations are given below.
i) C
2
H
5
OH+SOCl
2
→C
2
H
5
−Cl+SO
2
↓+HCl↓
ii) 2C
6
H
5
−Cl+2Na
ether
C
6
H
5
−C
6
H
5
+2NaCl
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