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MCAT Question A Day - 3/14/14 - Answer!

In the presence of a base, two molecules of an aldehyde or a ketone can combine to form a b-hydroxyaldehyde or b-hydroxyketone in an aldol condensation. Which of the following compounds will not react in an aldol condensation?

The correct answer is (C). If only (CH3)3CCHO and a strong base are present, no reaction can occur. For an aldol condensation to occur, the aldehyde or ketone must contain an a-hydrogen. The a-hydrogen is acidic and will combine with the base to form a carbanion. The carbanion is the nucleophile in the reaction that attacks the carbonyl carbon of another aldehyde or ketone molecule.

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