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Chapter 18 617
Copyright © 2017 Pearson Education, Inc.
Cl
NO
2
SO
3
H
NH
2
N
N
+
H
2
CrO
4
or
H
2
NNH
2
HO ,
Br
2
h
ν
H
2
/Raney Ni
H
2
/Pd/C
O
H
2
NH
2
Br
Br
2
,
FeBr
3
Cl
2
,
FeCl
3
HNO
3
,
H
2
SO
4
CH
3
CH
2
Cl,
AlCl
3
H
2
SO
4
CH
3
CCl
O
AlCl
3
1.
NaNO
2
,
HCl, 0
°
C
F
I
Cl
Br
OH
C
N
HBF
4
H
3
PO
2
CuCN
KI
CuBr
CuCl
H
2
, Raney Ni
Br
OH
COOH
HO
−
Br
OH
HBr
2. HO
−
,
,
H
2
O
H
2
O
2
H
2
SO
4
tert
-BuO
−
peroxide
1. R
2
BH/THF
Cu
(
NO
3
)
2
H
2
O
or
H
3
O
+
,
Cu
2
O
Pd/C
2. H
2
O
44.