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576 Chapter 17
Copyright © 2017 Pearson Education, Inc.
62.
O O
O
O O
O
O
_
HO
PBr pyridine
O O
1.
_
HO
H
1.
2.
2.
Br
OH
HCI
Br
2
3
O,
O
63.
+
CH
3
O
−
O
H
2
SO
4
O
OH
1. CH
3
CCH
2
COCH
3
O
CH
2
CH
2
CH
3
2. HCl,
or
H
2
O,
O
1. Br
1.
2. HCl, H
2
O
2
, H
3
O
+
−
2. CH
3
CO
2
3. HCl, H
2
O 1. LDA/THF
3 2 2
3
CH CH CH COCH
O
O
CH
2
CH
2
CH
3
1. LDA/THF
2. CH
3
CH
2
CH
2
Br
2. BrCH
2
1. LDA/THF
add slowly
add slowly
add slowly
O
CH
2
O
OH
CH
3
OCOCH
3
+
CH
3
O
−
HCl, H
2
O
O
1.
2.
O O
C
O
O
CH
2
CH
3
C
O
C
O
N
2.
Notice that the
b
-substituted compounds are prepared via an
a
,
b
-unsaturated ketone, which can be
prepared by dehydration of
a
-hydroxycyclohexanone.