JEE Main Chemistry question

The compound that doesn't undergo aldol condensation is

(A)A branched ketone with an α-CH (undergoes aldol)
(B)A phenylacetaldehyde-type compound with an α-CH₂ (undergoes aldol)
(C)A ketone flanked symmetrically by two gem-dimethyl groups, with no α-hydrogenCorrect
(D)A ketone bearing a tert-butyl group on one side and an enolizable methyl on the other (undergoes aldol via the methyl side)

Answer: (C)

Solution

Aldol condensation strictly requires at least one α-hydrogen on a carbon adjacent to the carbonyl. A ketone whose carbonyl carbon is flanked on both sides by fully substituted, quaternary (no-H) carbons (e.g. di-tert-alkyl ketones) has no available

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Question ID VK-149394