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218 Chapter 6
Copyright © 2017 Pearson Education, Inc.
43.
CH
2
CH
3
CCH
2
CH
2
CH
3
CH
2
Br
2
CH
2
CH
3
CCH
2
CH
2
CH
3
BrCH
2
Br
CH
2
CH
3
CCH
2
CH
2
CH
3
CH
2
H
2
CH
2
CH
3
CHCH
2
CH
2
CH
3
CH
3
Pd/C
CH
2
CH
3
CCH
2
CH
2
CH
3
CH
2
1. BH
3
CH
2
CH
3
CHCH
2
CH
2
CH
3
HOCH
2
2. HO
−
, H
2
O
2
, H
2
O
*
*
*
(* indicates an asymmetric center)
Each of the reactions forms a compound with one asymmetric center from a compound with no asymmet-
ric centers. Therefore, each of the products is a racemic mixture.
44.
Solved in the text.
45.
a.
CH
2
CH
3
C
H
Br
CH
2
CH
3
C
CH
3
H
Br
+
or
CH
3
CH
2
CH
3
Br
H
+
CH
3
CH
2
CH
3
Br
H
S
R
S
R
CH
3
b.
CH
3
CH
3
CH
2
CCH
2
CH
3
Br
This compound does not have an asymmetric center.
c.
Same as
b
.
d.
CH
2
CH
2
CH
3
C
H
Br
CH
2
CH
2
CH
3
C
CH
2
CH
3
H
Br
+
or
CH
2
CH
3
CH
2
CH
2
CH
3
Br
H
+
CH
2
CH
3
CH
2
CH
2
CH
3
Br
H
CH
3
CH
2
S
R
S
R
e.
C C
Br
H
Br
CH
2
CH
3
H
CC
CH
3
Br
H
Br
CH
3
CH
2
H
CH
3
Br
H
H
Br
CH
2
CH
3
CH
3
H
Br
Br
H
CH
2
CH
3
+
or
+
S S
R R
S
S
R
R
CH
3
f.
BrCH
2
CH
2
CH
2
CH
2
CH
3
C
Br
H
CH
2
CH
2
CH
2
CH
3
C
CH
2
Br
Br
H
+
or
H Br
CH
2
Br
CH
2
CH
2
CH
2
CH
3
+
Br
H
CH
2
Br
CH
2
CH
2
CH
2
CH
3
R
S
R
S