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Chapter 6 239

Copyright © 2017 Pearson Education, Inc.

101

.

a.

A proton adds to the alkene, forming a secondary carbocation, which undergoes a ring-expansion rear-

rangement to form a more stable tertiary carbocation.

CH H

3

C

CH

2

CHCH

3

H

3

C

H OSO

3

H

+

+

CH

3

CH

3

CH

3

H

HO CH

3

H

2

O

H

2

O

+

CH

3

CH

3

HO

+ H

3

O

+

102

.

103

.

a.

b.