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An organic compound (C3H9N) (A), when treated with nitrous acid, gave an alcohol and N2 gas was evolved. (A) on warming with CHCl3 and caustic potash gave (C) which on reduction gave isopropylmethylamine. Predict the structure of (A).

1. CH3 CH—NH2 CH3
2. CH3CH2—NH—CH3
3. CH3—N—CH3 | CH3
4. CH3CH2CH2—NH2

Correct answer: CH3CH2—NH—CH3

Solution

The compound (A) reacts with nitrous acid to give an alcohol and nitrogen gas, indicating it is a primary amine. The reaction with CHCl3 and caustic potash forming (C), which reduces to isopropylmethylamine, confirms the structure as CH3CH2—NH—CH3.

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