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358 Chapter 10
Copyright © 2017 Pearson Education, Inc.
The carbocations that are initially formed in
c
and
d
rearrange to form more stable carbocations.
c.
CH
3
C
CH
3
CH
3
CHCH
3
OH
HBr
CH
3
C
CH
3
CH
3
CHCH
3
OH
CH
3
C
CH
3
CH
3
CHCH
3
CH
3
C
CH
3
CHCH
3
CH
3
CH
3
C
CH
3
Br
CHCH
3
CH
3
secondary
carbocation
+
+
+
Br
−
1,2-methyl
shift
H
+
H
2
O
tertiary
carbocation
d.
+
OH
H
H
+
+
1,2-hydride
shift
Br
HBr
Br
OH
−
e.
OH
H
+
HCl
Cl
CH
3
OH
CH
3
+
H
CH
3
Cl
CH
3
+
CH
3
−
1,2-hydride
shift
f.
CH
3
CHCH
3
OH
CH
3
CHCH
3
OH
CH
3
CHCH
3
H
+
HCl
1,2-hydride
shift
CH
3
CH
2
CH
3
CH
3
Cl
CH
2
CH
3
Cl
−
tertiary
carbocation
secondary
carbocation
+
H
2
O
+
+
H