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542 Chapter 16
Copyright © 2017 Pearson Education, Inc.
c.
C
O
C
O
HCl
H
2
O,
SOCl
2
CH
3
OH
NHCH
3
C
O
OH
Cl
C
O
OCH
3
d.
2
C
O
C
O
CH OH
HCl
H
2
O,
1. LiAlH
4
2. H
3
O
+
NHCH
3
OH
73.
In parts
a
,
b
, and
d
, a new asymmetric center is formed in the product, so a racemic mixture is formed. In
part
c
, both
E
and
Z
stereoisomers are formed.
a.
O
CH
3
O
CH
3
c.
C C
N
H
3
C
H
C C
H
3
C
H N
b.
HO CH
3
HO CH
3
d.
C
CH
2
CH
2
CH
2
CH
3
CH
3
CH
2
H
OH
C
CH
2
CH
2
CH
2
CH
3
H CH
2
CH
3
HO
74.
a.
CH
3
CH
2
CH
2
CH
2
CH
2
CH
3
+
MgBr
CH
2
CH
3
CH
3
CH
2
CH
2
CH
2
MgBr
CH
2
CH
2
CH
2
CH
3
CH
3
CH
2
MgBr
+
+
C
O
C
O
C
O