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Which of the following compounds yields propylamine on hydrolysis?

1. CH3CH2C≡N
2. (CH3CH2CH2)2NH
3. CH3–C(=O)–NHCH2CH2CH3
4. CH3CH2–CH=NH

Correct answer: CH3–C(=O)–NHCH2CH2CH3

Solution

CH3-CO-NH-CH2CH2CH3 (N-propylacetamide) on hydrolysis gives acetic acid plus propylamine (CH3CH2CH2NH2). Nitrile hydrolysis would give an acid, not an amine, so it is the amide that yields propylamine.

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