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Carbylamine is obtained when aniline is

  • A.heated with Con.\(\mathrm{H_{2}SO_{4}}\)
  • B.treated with \(\mathrm{NaNO_{2} / HCl}\)
  • C.heated with \(\mathrm{CHCl_{3}}\) and ethanolic \(\mathrm{KOH}\)
  • D.treated with \(\mathrm{CHCl_{3}}\) and \(\mathrm{HCl}\)
  • E.treated with \(\mathrm{HCl}\)

Answer: C

The carbylamine is obtained when aniline is heated with \(\mathrm{CHCl_{3}}\) and ethanolic KOH.

This is the carbylamine reaction (isocyanide test). A primary amine heated with chloroform and alcoholic potassium hydroxide gives an isocyanide, which has a very unpleasant smell:

\[ \begin{aligned} &\mathrm{C_{6}H_{5}NH_{2} + CHCl_{3} + 3KOH} \\ &\mathrm{\rightarrow C_{6}H_{5}NC + 3KCl + 3H_{2}O} \end{aligned} \]

The base is essential, since it generates dichlorocarbene from chloroform, so chloroform with HCl does nothing of the kind. \(\mathrm{NaNO_{2} / HCl}\) diazotises aniline, concentrated \(\mathrm{H_{2}SO_{4}}\) on heating sulphonates it (sulphanilic acid), and HCl alone just forms anilinium chloride.

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