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Chapter 16 549
Copyright © 2017 Pearson Education, Inc.
88.
H
3
C
O
O
O
CH
3
CH
3
HB
+
+
O
O
O
H
3
C
CH
3
CH
3
H
B
+
H CH
3
H CH
3
+
H CH
3
H B
+
C
O
C
OH
C
O
CH CH
3
OH
O
CH
CH
3
+
C
O
CH
3
H
+
CH CH
3
OH
O
CH
CH
3
C
O
CH
3
H
89.
a.
CH O
CH
+
(C
6
H
5
)
3
P CHCH
2
CH
2
CH
3
or
P(C
6
H
5
)
3
+
O CHCH
2
CH
2
CH
3
b.
P(C
6
H
5
)
3
(C
6
H
5
)
3
P CHCH
2
CH
3
+
or
+
O CHCH
2
CH
3
O
c.
+
CH
(C
6
H
5
)
3
P
CH O
d.
O
+
(C
6
H
5
)
3
P CH
2
or
P(C
6
H
5
)
3
+
O CH
2
90.
The first step is conjugate addition of an organocuprate, and the second step is direct addition of a Grignard
reagent.
(CH
2
CH)
2
CuLi
THF
1. CH
3
MgBr
CH
2
CHCCH
2
CHCH
3
CH
3
CH
3
OH
A
B
2. H
3
O
+
CH H
CH
3
C
CH
3
CH
2
H
CHC
CH
3
CH
2
CH
3
C
O
C
O