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How many of the following compounds give a foul-smelling product (isocyanide) when treated with NaOH and CHCl3 (carbylamine reaction)? The compounds are: (1) CH3-NH2, (2) CH3CH2CH(NH2)CH3, (3) (CH3)3C-NH2, (4) a cyclic tertiary amine with N in the ring, (5) aniline (C6H5-NH2), (6) benzylamine (C6H5-CH2-NH2), (7) acetamide (CH3-CO-NH2), (8) diethylamine ((C2H5)2NH), (9) (C2H5)2N-I, (10) CH3CH2CH2-NH2, (11) p-toluidine (p-CH3-C6H4-NH2).

1. 5
2. 6
3. 7
4. 8

Correct answer: 7

Solution

Carbylamine reaction is specific to primary amines; compounds 1, 2, 3, 5, 6, 10, and 11 are all primary amines and give isocyanide (foul smell), giving a count of 7.

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