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Which of the following amines cannot be formed from the reduction of amides with LiAlH4?

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in Chemistry – Class 12 by (188k points)
Which of the following amines cannot be formed from the reduction of amides with LiAlH4?

(a) Ethylamine

(b) Benzenamine

(c) Benzylamine

(d) Ethylmethylamine

I have been asked this question by my college director while I was bunking the class.

This question is from Preparation of Amines topic in portion Amines of Chemistry – Class 12

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Correct answer is (b) Benzenamine

Easy explanation: The -CONH2 group of amides is reduced to a -CH2NH2 group and results in a compound having the same number of carbon atoms. The simplest aromatic amide is benzamide, which is reduced to give benzylamine. Hence, aniline cannot be formed as there is no corresponding amide that can be reduced to it with LiAlH4. However, it can be achieved by Hoffmann bromamide degradation.

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