(a) Write the structures of the main products of the following reactions :

(b) Give a simple chemical test to distinguish between Aniline and N, N-dimethylaniline.

(c) Arrange the following in the increasing order of their $p K_{b}$ values :
$C_{6} H_{5} N H_{2}, C_{2} H_{5} N H_{2}, C_{6} H_{5} N H C H_{3}$

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Solution

(b) Aniline + $C H C I_{3} + K O H \to A l k y l i s o c y a n a t e (s t r o n g s m e l l i n g s u b s t a n c e)$

N, N-dimethylaniline + $C H C I_{3} + K O H \to$ No reaction

(c) $C_{2} H_{5} N H_{2} < C_{6} H_{5} N H C H_{3} < C_{6} H_{5} N H_{2}$

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p K_{b}

C_{6} H_{5} N H_{2}, C_{2} H_{5} N H_{2}, C_{6} H_{5} N H C H_{3}

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C_{6} H_{5} N H_{2}, C_{2} H_{5} N H_{2}, C_{6} H_{5} N H C H_{3}

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