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An aromatic compound (X) of molecular formula, C7H7Cl, on ammonolysis gives Y(Molecular formula, C7H9N) . The compound 'Y' reacts with two moles of CH3Cl gives N, N-Dimethylphenylmethanamine. The compounds 'X' and 'Y' are

  • A.Benzylchloride and Aniline
  • B.Chlorobenzene and Aniline
  • C.Benzylchloride and Benzylamine
  • D.Chlorobenzene and Benzylamine
  • E.Benzoylchloride and Benzylamine.

Answer: C

X and Y are Benzylchloride and Benzylamine.

\(C_{7}H_{7}Cl\) with a reactive (side-chain) chlorine is benzyl chloride, \(C_{6}H_{5}CH_{2}Cl\). Ammonolysis gives benzylamine, \(C_{6}H_{5}CH_{2}NH_{2}\) (\(C_{7}H_{9}N\)), and two methylations give \(C_{6}H_{5}CH_{2}N(CH_{3})_{2}\), N,N-dimethylphenylmethanamine.

Chlorobenzene is \(C_{6}H_{5}Cl\) and aniline \(C_{6}H_{7}N\), so they do not fit the formulas (and aryl halides resist ammonolysis). Benzoyl chloride is \(C_{7}H_{5}OCl\).

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