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Chapter 27 829
Copyright © 2017 Pearson Education, Inc.
10.
a.
O
CH
3
CH
3
−
RO CH
2
CO
−
RO
CH
3
CH
3
O
CH
3
CH
3
RO CH
2
CO
CH
3
CH
3
−
RO CH
2
COCH
2
CO
−
CH
3
CH
3
CH
3
CH
3
O
CH
3
CH
3
−
RO CH
2
COCH
2
COCH
2
CO
−
CH
3
CH
3
CH
3
CH
3
RO CH
2
COCH
2
CO
CH
3
CH
3
CH
3
CH
3
CH
3
CH
3
b.
O
H B
+
CH
3
CH
3
HO
CH
3
CH
3
+
HO
CH
3
CH
3
+
O
CH
3
CH
3
O
HOCH
2
C
CH
3
CH
3
CH
3
CH
3
+
O
HOCH
2
C
CH
3
CH
3
CH
3
CH
3
+
O
CH
3
CH
3
O
HOCH
2
COCH
2
C
CH
3
CH
3
CH
3
CH
3
+
CH
3
CH
3
11.
In anionic polymerization, nucleophilic attack occurs at the less substituted carbon because it is less
sterically hindered; in cationic polymerization, nucleophilic attack occurs at the more substituted carbon
because the ring opens to give the more stable partial carbocation (Section 10.7).
O
CH
3
position of nucleophilic attack
in anionic polymerization
position of nucleophilic attack
in cationic polymerization
12.
a.
CH
2
CCH
3
CH
3
+
BF
3
+
H
2
O
b.
N
CH CH
2
+
BF
3
+
H
2
O
O
c.
+
CH
3
O
−
O
d.
CH
2
CH
+
BuLi
COCH
3
O