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Chapter 16 531
Copyright © 2017 Pearson Education, Inc.
b.
Br
1.
CH
2
Br
3.
2.
CH
3
CH
2
Br
CH
3
CH
2
CH
2
Br
CH
3
Br
(C
6
H
5
)
2
CHBr
or
or
or
c.
The best set of reagents is the pair that has the ylide synthesized from the less sterically hindered
alkyl halide.
O
CH O
(C
6
H
5
)
2
C O
1.
CH
3
CH
2
CH P(C
6
H
5
)
3
2.
CH
3
CH P(C
6
H
5
)
3
3.
CH
2
P(C
6
H
5
)
3
+
+
+
50.
a.
Br
3
) CuLi
Br
2
hv
CH
3 2
Br
CH
3
CH
3
HO
−
b.
Br
MgBr
CH
2
Mg
Et
2
O
HCH
O
H
3
O
+
CH
2
OH
O
−
c.
Br
MgBr
COO
−
Mg
Et
2
O
H
3
O
+
COOH
CO
2
Br
C
COOH
HCl, H
2
O
C N
−
N
or
d.
Br
CuLi
CH
2
CH OH
2
1. Li
2. CuI
2. HCl
2
1.
O