372 / 912
364 Chapter 10
Copyright © 2017 Pearson Education, Inc.
b. 1.
CH
3
CH
2
CCH
2
CH
3
O
2.
CH
3
CH
2
CH
2
CH
2
CH
O
3.
A tertiary alcohol is not
oxidized to a carbonyl compound.
4.
CH
2
CCH
2
CCH
2
CH
3
O O
5.
O
6.
HCCH
2
CH
2
CH
O O
c.
The same products as formed in
b
.
23.
Solved in the text.
24.
a.
Cleavage occurs by an
S
N
1
pathway because the allyl cation is relatively stable.
H
HO
I
I
O
_
+
+
+
b.
Cleavage occurs by an
S
N
2
pathway because a primary carbocation is too unstable to be formed.
HOCH
2
CH
2
CH
2
CH
2
CH
2
I
I
−
O
H
+
c.
Cleavage occurs by an
S
N
1
pathway because the benzyl cation is relatively stable.
CH
2
CH
2
I
HO
+
CH
2
O
H
+
I
−
+
d.
Cleavage occurs by an
S
N
1
pathway because the benzyl cation is relatively stable.
CH
3
CH
2
CH
2
OH
+
+
CH
2
ICH
2
CH
3
CH
2
CH
2
I
−
O
H
CH
2
+