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582 Chapter 17
Copyright © 2017 Pearson Education, Inc.
71.
a.
CH
2
CH
2
CH
2
CH
2
CH
2
Br
1. CH
3
CH
2
O
−
2. Br(CH
2
)
5
Br
OH
CH
3
CH
2
O
−
HCl, H
2
O
CO
2
+
+
2 CH
3
CH
2
OH
C
2
H
5
O
OC
2
H
5
OC
2
H
5
CH
C
O
C
O
C
O
C
C
O
C
2
H
5
O
OC
2
H
5
CH
2
C
O
C
O
OC
2
H
5
O
b.
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
Br
1. CH
3
CH
2
O
−
2. Br(CH
2
)
5
Br
CH
3
CH
2
O
−
malonic ester
HCl, H
2
O
4 CH
3
CH
2
OH
+
2 CO
2
+
C
O
C
O
HO
OH
C
O
C
O
CH
C
O
C
O
(CH
2
)
7
CH
2
CH
2
CH
2
CH
2
CH
2
CH
C OC
2
H
5
C OC
2
H
5
C
O
C
O
C
2
H
5
O
OC
2
H
5
CH
C
2
H
5
O
OC
2
H
5
C
2
H
5
O
OC
2
H
5
O
O
72.
a.
The first reaction is an intermolecular Claisen condensation. An intramolecular condensation reaction
forms the final product. Notice that the most acidic hydrogen is the one removed for the intramolecular
condensation.
O
O
O
O
O
O
O
O
_
O
O
H
O
O
O
O
O
_
_
B
O
O
O
O
O
O
O
O O
O
O
C O