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Chapter 15 503
Copyright © 2017 Pearson Education, Inc.
67.
1-Bromobutane undergoes an S
N
2 reaction with NH
3
to form butylamine
(A)
. Butylamine can then react
with 1-bromobutane to form dibutylamine
(B)
. The amines each form an amide upon reaction with acetyl
chloride. The IR spectrum of
C
exhibits an NH stretch at about
∼
3300 cm
-
1
, whereas the IR spectrum of
D
does not exhibit this absorption band because the nitrogen in
D
is not bonded to a hydrogen.
NH
3
CH
3
CH
2
CH
2
CH
2
NH
2
A
(CH
3
CH
2
CH
2
CH
2
)
2
NH
B
CH
3
CH
2
CH
2
CH
2
Br
CH
3
CH
2
CH
2
CH
2
Br
CH
3
CH
2
CH
2
CH
2
NH
2
CH
2
CH
2
CH
2
CH
3
+
(CH
3
CH
2
CH
2
CH
2
)
2
NH
(CH
2
CH
2
CH
2
CH
3
)
2
+
A
C
B
D
C
Cl
CH
3
O
C
Cl
CH
3
O
C
NH
N
CH
3
O
C
CH
3
O
68.
O
−
NH
2
O
O
i.
OCH
3
O
OCH
3
O
j.
O
O
O
h.
g.
+
CH
2
OH
C
CH
3
O
C
OCH
3
CH
3
O
O
O O
e.
O
CH
2
CH
2
CH
2
OH
f.
C
HO
a.
C
F
CH
3
O
CH
2
CH
2
CH
2
NH
3
+
Cl
−
b.
C
HO
O
c.
C
O
NHCH
3
d.
HO CH
2
CH
2
OH
C
O
C
O