Arrange the following in decreasing order of their basic strength:

$C_{6} H_{5} N H_{2}, C_{2} H_{5} N H_{2}, (C_{2} H_{5})_{2} N H, N H_{3}$

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Solution

The decreasing order of basic strength is:
$(C_{2} H_{5})_{2} N H > C_{2} H_{5} N H_{2} > N H_{3} > C_{6} H_{5} N H_{2}$
Ammonia is more basic than aniline as in aniline, the lone pair of electron on N atom is in resonance with benzene ring. Hence, it cannot be donated easily.
Ethyl amine is more basic than ammonia because in ethyl amine, the $+ I$ effect of ethyl group increases the electron density on $N$ .
Diethylamine is most basic due to $+ I$ effect of two ethyl groups.

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