Chemistry Reference
In-Depth Information
g.
p
-chlorobenzenediazonium chloride
h.
N
-methyl-
p
-methoxyaniline
i.
trans
-1,3-diaminocyclobutane
j. 1,6-diaminohexane
11.26
CH
3
CH
2
CH
2
CH
2
NH
2
n
-butylamine or 1-butanamine (primary)
CH
3
CH
2
CH(NH
2
)CH
3
2-butylamine or 2-butanamine (primary)
(CH
3
)
2
CHCH
2
NH
2
2-methylpropanamine (primary)
(CH
3
)
3
CNH
2
2-methyl-2-propanamine or
t
-butylamine (primary)
CH
3
CH
2
CH
2
NHCH
3
N
-methylpropanamine (secondary)
(CH
3
)
2
CHNHCH
3
N
-methyl-2-propanamine (secondary)
(CH
3
CH
2
)
2
NH
diethylamine or
N
-ethylethanamine (secondary)
(CH
3
)
2
NCH
2
CH
3
ethyldimethylamine or
N,N
-dimethylethanamine (tertiary)
11.27
a.
Aniline is the stronger base. The
p
-cyano group is electron-withdrawing and
therefore decreases the basicity of aniline. Note that the possibilities for
delocalization of the unshared electron pair are greater in
p
-cyanoaniline than
in aniline.
H
+
N
C
N
H
N
C
N
-
H
H
Resonance stabilizes the free base relative to its protonated form, and the
effect is greater with
p
-cyanoaniline than with aniline.
b.
The possibilities for delocalization of an electron pair are greater in
diphenylamine than in aniline (two phenyl groups versus one phenyl group).
Thus, aniline is the stronger base.
