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534 Chapter 16
Copyright © 2017 Pearson Education, Inc.
56.
and
O
CH
3
CH
2
CH
2
CH
2
CH
2
CH
3
O
C
O
CH
3
CH
2
CH
2
CH
2
CH
3
CH
2
O
C
57.
a.
1. LiAlH
4
2. H
3
O
+
RCH
2
OH
HI
RCH
2
OCH
3
1. LiAlH
4
2. H
3
O
+
R CH CH
2
1. NaBH
4
2. H
3
O
+
1. R
2
BH/THF
2. HO
−
, H
2
O , H
2
O
2
RCH
2
Br
1. NaBH
4
2. H
3
O
+
1. NaBH
4
2. H
3
O
+
H
2
C O
1.
1.
RMgBr
2. H
3
O
+
(R )
2
CuLi
2. H
3
O
+
O
1. CH
3
COO
−
2. HCl, H
2
O
R H
C
O
R OH
C
O
R OR
C
O
R Cl
C
O
R O
C
O
R
C
O
b.
The reaction of an organocuprate with ethylene oxide leads to
R CH
2
CH
2
OH.
Because this alcohol does
not have a methyl group on the
b
-carbon, this method cannot be used to synthesize isobutyl alcohol.
R CH
2
CH
2
OH cannot lead to CH
3
CHCH
2
OH
CH
3
58.
a.
C C
CH
3
CH
2
CH
2
H
H
CH
3
reduction
b.
CH
3
CH
2
CH
2
NHCH
3
reduction
c.
CH
2
CH
2
CH
3
reduction
d.
CH
2
OH reduction
e.
CH
2
OH
+ CH
3
OH
reduction
f.
C
OH
O
oxidation
59.
a.
6-methyl-4-hepten-3-one
b.
6-ethoxy-5-ethyl-2,2-dimethyl-4-heptanol
c.
(
S
)-4-methylhexanal
d.
5-amino-6-hydroxy-2-heptanone