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568 Chapter 17
Copyright © 2017 Pearson Education, Inc.
37.
a.
O
O
HO
−
O
3
O
OCH
−
CH
3
CH O
3
CH
2
CH CH
2
H
H
+
C
O
C
O
C
O
retrosynthetic
analysis
synthesis
3
OCH
3
O OCH
O
O
b.
CH
3
O
CH
3
O
CH
CH
O
CH
3
O
HO
−
−
CH
2
CH CH
3
O
3
CH CH
2
H
+
2
C
O
OCH
3
3
C
O
OCH
C
O
OCH
3
C
O
C
O
retrosynthetic
analysis
synthesis
CH
C
O
c.
CH
3
O
O
retrosynthetic
analysis
CH
3
O
O
H
3
C
O
−
+
O
H
3
C
O
HO
−
CH
3
O
H
3
C
H
3
C
O
CH
2
CH
3
CH CH
2
C
O
38.
A
and
D
are
b
-keto acids, so they can be decarboxylated on heating.
B
cannot be decarboxylated because it does not have a carboxyl group.
The electrons left behind if
C
were decarboxylated cannot be delocalized onto an oxygen.