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Question
Give one chemical test to distinguish between the following pair of compounds.
Aniline and benzylamine
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Solution
Aniline and benzylamine can be distinguished by their reactions with the help of nitrous acid, which is prepared in situ from a mineral acid and sodium nitrite. Benzylamine reacts with nitrous acid to form unstable diazonium salt, which in turn gives alcohol with the evolution of nitrogen gas.
\[\ce{\underset{Benzylamine}{C6H5CH2 - NH2} + HNO2 ->[NaNO2 + HCl] \underset{(Unstable)}{[C6H5CH2 - \overset{+}{N2}C\overset{-}{l}]} ->[H2O] N2 ^ + \underset{Benzy alcohol}{C6H5CH2 - OH} + HCl}\]
On the other hand, aniline reacts with HNO2 at a low temperature to form stable diazonium salt. Thus, nitrogen gas is not evolved.
\[\ce{C6H5NH2 ->[NaNO2 + HCl][273 - 278 K] C6H5 - \overset{+}{N2}C\overset{-}{l} + NaCl + 2H2O}\]
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