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Which of the following compounds is converted to the corresponding hydrocarbon on reduction with zinc and hydrochloric acid?

1. Acetamide
2. Ethanoic acid
3. Ethyl ethanoate
4. Butan-2-one

Correct answer: Butan-2-one

Solution

Zinc and HCl (Clemmensen-type) reduces a carbonyl group to a methylene, giving the hydrocarbon. Of the choices only butan-2-one (a ketone) is reduced this way (to butane); acids, esters and amides are not converted to hydrocarbons under these conditions.

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