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A mixture of primary amides (containing a benzene ring) with molecular formula C8H9NO is treated with Br2/NaOH (Hofmann bromamide reaction). How many distinct primary amine products can be formed?

1. 1
2. 2
3. 3
4. 4

Correct answer: 4

Solution

Primary amides with formula C8H9NO and a benzene ring: (1) o-methylbenzamide, (2) m-methylbenzamide, (3) p-methylbenzamide, (4) phenylacetamide (PhCH2CONH2). Hofmann degradation (Br2/NaOH) converts RCONH2 to RNH2. Products: o-toluidine, m-toluidine, p-toluidine, and benzylamine — 4 distinct primary amine products.

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