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The carbylamine reaction involves treating a compound with chloroform (CHCl3) and aqueous KOH (or NaOH), producing a foul-smelling isocyanide if a primary amine is present. Which of the following compounds will NOT produce a foul smell in this reaction?

1. CH3CONH2 (acetamide)
2. C6H5NHCH3 (N-methylaniline)
3. (C2H5)3N (triethylamine)
4. CH3CH2CH2C(CH3)2NH2 (2-methyl-1-butanamine neopentyl type primary amine)

Correct answer: CH3CONH2 (acetamide)

Solution

CH3CONH2 is an amide, not a primary amine; the nitrogen lone pair is delocalized into the carbonyl group, making it unreactive under carbylamine conditions and producing no foul smell. The other options include a secondary amine, a tertiary amine (also non-reactive), and a primary amine that would give foul isocyanide — but the question targets the compound that definitively does not react, which is the amide.

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