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Question
Give one chemical test to distinguish between the following pair of compounds.
Aniline and benzylamine
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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