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Chapter 6 225
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64.
HBr
H
2
SO
4
H
2
SO
4
H
2
RCOOH
H
2
, Pd/C
Br
2
CH
2
Cl
2
H
Br
2
2
1. R
2
BH/THF
2. H
2
O H
2
O
2
, HO ,
−
CH
3
OH
O
Br
Br
Br
OH
OH
OH
Br
O
OCH
3
O
H
1. O
3
, –78
°
C
2. (CH
3
)
2
S
O
O
65.
a.
and
CH
2
CH
3
b.
(Note: D stands for deuterium, an isotope of hydrogen; DBr reacts in a manner similar to HBr.) While HBr
forms the same product when it reacts with the two alkenes, DBr forms different products. They are shown here.
CH
3
Br
D
and
CH
2
D
Br
66.
a.
Cl
b.
Br
OCH
3
CH
3
O
+
Br
c.
O O
+
d.
OH
e.
Cl
OH HO
+
Q
f.
O
O
H
67.
a.
Pd/C
H
2
b.
CH
3
CH
2
CH
2
CH CH
2
HCl
c.
1. R
2
BH/THF
2. H
2
O
2
, HO
−
,
H
2
O
CH
2
d.
CH CH CH CHCH
3
CH
Br
2
H
2
O 3
2
2
e.
H
2
SO
4
H
2
O
CH
2
CH CH
2
f.
CH CH CH CHCH
3
CH
Cl
2
NaBr
excess
3
2
2
3 2
2 3
CH CH CH CHCH CH
Br
2
NaCl
excess
or
g.
OCH
3
h.
+
Cl
Cl
Cl
Cl