The carbonyl compound shown reacts with ethylmagnesium bromide, and the adduct is hydrolysed with dilute acid. Which structure is the product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: B

Methanal (formaldehyde) has two hydrogens on the carbonyl carbon, so addition of the ethyl carbanion gives, after hydrolysis, a primary alcohol with one more carbon than the Grignard alkyl group: propan-1-ol. Secondary and tertiary alcohols require an aldehyde other than methanal or a ketone.

Practice Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition More on Grignard, cyanide and hydride addition products

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