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Which of the following amines gives a positive Liebermann nitroso test?

1. 2-butanamine
2. N-ethyl-2-pentanamine
3. N-methylpiperidine
4. N,N-dimethylcyclohexylamine

Correct answer: N-ethyl-2-pentanamine

Solution

Liebermann nitroso test detects secondary amines. 2-butanamine is a primary amine (one N-H, two H's on N — actually three H's on N for primary: NH2). N-ethyl-2-pentanamine is a secondary amine (N has one H, two alkyl groups). N-methylpiperidine is a tertiary amine (cyclic, N has no H). N,N-dimethylcyclohexylamine is a tertiary amine. Only N-ethyl-2-pentanamine is secondary.

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