Which of the following compounds on reduction with lithium aluminium hydride ( LiAlH₄ ) yields N-methylaniline?

Step-by-step solution

N-methylaniline ( C₆H₅NHCH₃ ) is a secondary amine. Reduction of an isocyanide ( R-NC ) with LiAlH₄ yields a secondary amine containing a methyl group ( R-NHCH₃ ). Therefore, phenyl isocyanide ( C₆H₅NC ) upon reduction gives N-methylaniline. Benzonitrile ( C₆H₅CN ) and benzamide ( C₆H₅CONH₂ ) on reduction yield benzylamine ( C₆H₅CH₂NH₂ ), which is a primary amine. Benzyl isocyanide ( C₆H₅CH₂NC ) on reduction yields N-methylbenzylamine ( C₆H₅CH₂NHCH₃ ). Answer: Phenyl isocyanide