Distinguish between $C_{6} H_{5} N H_{2}$ and $C_{6} H_{5} N H C H_{3}$ .

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Solution

$C_{6} H_{5} N H C H_{3}$ or benzylamine is characterized by the evolution of $N_{2}$ gas when reacted with nitrous acid as shown below

$C_{6} H_{5} N H C H_{3} + (N a N O_{2} + H C l) \to C_{6} H_{5} C H_{2} O H + N_{2} + H C l$

On the other hand, $N_{2}$ gas is not evolved when $C_{6} H_{5} N H_{2}$ or aniline reacts with nitrous acid.

$C_{6} H_{5} N H_{2} + (N a N O_{2} + H C l) \to {C_{6} H_{5} N_{2}}^{+} C l^{-} + 2 H_{2} O + N a C l$

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