577 / 912
Chapter 17 569
Copyright © 2017 Pearson Education, Inc.
39.
a.
methyl bromide
b.
methyl bromide (twice)
c.
benzyl bromide
d.
isobutyl bromide
40.
a.
An S
N
2 reaction cannot be done on bromobenzene. (See page 436 of the text.)
b.
An S
N
2 reaction cannot be done on vinyl bromide. (See page 436 of the text.)
c.
An S
N
2 reaction cannot be done on a tertiary alkyl halide. (Only elimination occurs; see Table 9.7 on
page 432 of the text.)
41.
a.
ethyl bromide
b.
pentyl bromide
c.
benzyl bromide
42.
Solved in the text.
43.
C
CH
3
O
N
H
C
N
CH
2
CH
3
CH
2
Br
C
CH
2
CH
2
CH
3
N
C
CH
2
CH
2
CH
3
+
Br
−
HCl H
2
O
C
O
+
N
+
H H
Cl
−
−
a.
trace
acid
C
CH
3
O
or
LDA / THF
C
CH
2
CH
3
CH
2
Br
C
CH
2
CH
2
CH
3
O
OH
b.
CH
3
O
−
O
O
O
O
COCH
3
COCH
3
1. CH
3
O
−
2. CH
3
CH
2
Br
HCl
H
2
O
O
CH
2
CH
3
CH
2
CH
3
c.
H HO
+
_
C
O
+
CO
2
H
2
O
+
CH
3
O
OCH
3
(CH
2
)
5
CH CH
C
O
C
O
CHCH
2
H
H
C
O
C
O
1.
CH
3
H
C
O
add slowly
2. HCl