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Chapter 11 399
Copyright © 2017 Pearson Education, Inc.
20.
Suzuki reactions
a.
Br
+
B
OR
OR
CH
3
CH
2
C CH
HB(OR)
2
PdL
2
HO
−
Br
+
OR
OR
B
CH
3
CH
2
CH CH
2
HB(OR)
2
PdL
2
HO
−
b.
Br
+
B
OR
OR
CH
3
CH
2
C CH
HB(OR)
2
PdL
2
HO
−
Br
+
OR
OR
B
CH
3
CH
2
CH CH
2
HB(OR)
2
PdL
2
HO
−
Heck reactions
a.
Br
+
PdL
2
(CH
3
CH
2
)
3
N
Br
+
PdL
2
(CH
3
CH
2
)
3
N
H
2
Pd/C
b.
Br
+
PdL
2
(CH
3
CH
2
)
3
N
Br
+
PdL
2
(CH
3
CH
2
)
3
N
H
2
Pd/C
Notice that only a Suzuki reaction can be used to replace a halogen with an alkyl group. A Heck reaction replaces
a halogen wih an alkenyl group. However, the alkenyl group can subsequently be reduced to an alkyl group.
21.
Br
CH
3
C
O
CH
CH
3
O
CH
2
+
Br
CH
3
O
CH
CH
3
C
O
CH
2
+
or
22.
a.
Z
+
CH
2
CH
2
CH
3
CH
2
CH CHCH
2
CH
3
E
and
b.
+
CH
2
CH
2
+
c.
+
CH
2
CH
2
C C
CH
3
CH
3
CH
3
CH
3
d.
+
CH
2
CH
2