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530 Chapter 16
Copyright © 2017 Pearson Education, Inc.
c.
The carbonyl group has to be protected to prevent it from reacting with the Grignard reagent.
This synthesis is easier to understand if the
CO
2
needed in the third step is written as
O
“
C
“
O.
C
H
H
Br
O
HCl
HOCH
2
CH
2
OH
Br
O
O
Mg
Et
2
O
MgBr
O
O
O C
COO
−
O
O
H
2
O HCl
C
COOH
O
O
47.
a.
O CH
2
CH
3
C
O
c.
O
O
CH
3
b.
OH
C
O
d.
O
O
48.
Solved in the text.
49.
O
+
CH
3
CH
2
CH P(C
6
H
5
)
3
1.
P(C
6
H
5
)
3
+
CH
3
CH
2
CH O
or
2.
b.
a.
(C
6
H
5
)
2
C O
+
CH
3
CH P(C
6
H
5
)
3
or
(C
6
H
5
)
2
C P(C
6
H
5
)
3
+
CH
3
CH O
CH O
CH
2
P(C
6
H
5
)
3
+
3.
CH P(C
6
H
5
)
3
CH
2
O
+
or