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Chapter 16 537
Copyright © 2017 Pearson Education, Inc.
62.
a.
SOCl
pyridine
2
1. NaBH
4
2. H
3
O
+
CH
3
CH
2
CH
2
OH
O
C
H
O
C
OH
O
C
Cl
O
C
O
H
2
CrO
4
b.
1. CH
3
CH
2
MgBr
2. H
3
O
+
O
OH
O
C
H
OH
NaOCl
CH
3
COOH
0 ºC
NaOCl
CH
3
COOH
0 ºC
c.
OH
O
1. CH
3
NH
2
2. NaBH
3
CN
NHCH
3
NaOCl
CH
3
COOH
0
°
C
d.
O
OH
1. NaBH
4
2. H
3
O
+
H
2
SO
4
2. (CH
3
)
2
S
1. O
3
,
−
78
°
C
H
O
O
H
HO
O
O
OH
H
2
CrO
4
e.
O
1. CH
3
MgBr
H
2
SO
4
2. HCl
CH
3
OH
CH
3
2. (CH
3
)
2
S
1. O
3
,
−
78
°
C
H
O
O
OH
O
O
H
2
CrO
4