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Solutions for Amines
Br N
28 (a)
(b) Use a large excess of ammonia to avoid multiple alkylations of each nitrogen.
+ NH3
SN2 Br–
H
H H
NH3
N
H
H
Br
N
H
H
NH3
N H
Good nucleophile—alkylation 
process can continue.
Br–
29
N
O
O
O
O
N
N
O
O
BrCH2Ph
Br(CH2)5CH3
Br(CH2)3COO
O
O
N CH2Ph
N (CH2)5CH3
O
O
O
O
N (CH2)3COO
NH2NH2
NH2NH2
H2NCH2Ph
H2N(CH2)5CH3
H2N(CH2)3COOH
Must use anion
to avoid protonating
the phthalimide anion.
2) H—A
1) NH2NH2 , ∆
(c)
(b)
(a)
∆
∆
Br C N
NH2
(a)
30 Assume that LiAlH or H /catalyst can be used interchangeably.4 2
(b) 1) LiAlH4
2) H2O
PhCH2Br + NaN3 PhCH2NH2Pt
H2
KCN
PhCH2N3
OH
O
NH2
OH
TsCl
N3
OTs
NaN3
(c)
1) LiAlH4
2) H2O
pyridine2) H2O
1) LiAlH4
OH
O
NH2
1) LiAlH4 2) H2O
OR SOCl2
Cl
O NH3
NH2
O
462