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Which of the following transformations does not produce a primary amine?

1. CH3CONH2 treated with Br2/KOH
2. CH3CN treated with LiAlH4
3. CH3NC treated with LiAlH4
4. CH3CONH2 treated with LiAlH4

Correct answer: CH3NC treated with LiAlH4

Solution

CH3-NC reduced by LiAlH4 gives the secondary amine dimethylamine (CH3)2NH, not a primary amine. The other three (amide+Br2/KOH, CH3CN+LiAlH4, amide+LiAlH4) all give primary amines.

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