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Chapter 10 363
Copyright © 2017 Pearson Education, Inc.
18.
Both alcohols form the same carbocation, so they both form the same alkenes.
H
2
SO
4
+
+
+
–
H
+
+
H
1,2-hydride
shift
+
–
H
+
1,2-hydride
shift
H
2
SO
4
H
2
O
+
OH
H
OH
H
OH
H
2
O
OH
+
+
+
+
+
19.
a.
H
H
CH
2
CH
3
+
major
CH
3
H
CH
2
CH
3
H
minor
CH
3
CH
3
CH
3
+
major
CH
2
CH
3
minor
CH
3
CH
2
CH
3
CH
3
CH
2
CH
2
CH
3
CH
3
C C
C C
C C
C C
20.
a.
CH
3
CH
2
C CCHCH
3
CH
3
CH
3
CH
2
CH
3
b.
C C
CH
2
CH
3
CHCH
3
CH
2
CH
3
CH
3
CH
3
21.
a.
CH
3
CH
2
CHCH
2
OH
CH
3
b.
CH
3
OH
c.
CH
3
CH
2
CHCH
2
CH
3
OH
d.
CH
2
OH
22.
a.
The answers to
1, 3, 4,
and
5
are the same as in part
b
.
2.
CH
3
CH
2
CH
2
CH COH
2
O
6.
HOCCH COH CH
2 2
O O
b.