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On treatment with lithium aluminium hydride, which of the following gives a secondary amine as the product?

1. Methyl isocyanide
2. Acetamide
3. Methyl cyanide
4. Nitroethane

Correct answer: Methyl isocyanide

Solution

Reduction of methyl isocyanide (CH3-NC) with LiAlH4 gives N,N-dimethylamine, CH3-NH-CH3, a secondary amine. Acetamide and methyl cyanide both reduce to primary amines.

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