An organic chemist is planning to synthesize a larger molecule via an aldol condensation reaction. Which of the following structural features is absolutely essential for at least one of the carbonyl reactants to participate in this reaction?
Show answer and explanation
The answer
Correct answer: D. The carbonyl compound must possess at least one hydrogen atom on the alpha-carbon adjacent to the carbonyl group.
Tested concept: Aldol condensation
Explanation
Aldol condensation reactions proceed through the formation of an enolate ion, which acts as a nucleophile. Enolate formation requires the presence of an acidic alpha-hydrogen atom on the carbon adjacent to the carbonyl group. Without an alpha-hydrogen, an enolate cannot form, and thus the compound cannot participate as the enolate component in an aldol condensation. While aldehydes are generally more reactive, ketones can also undergo aldol condensation if they possess alpha-hydrogens. The reaction is a condensation, not an oxidation, and does not typically involve strong oxidizing agents. Carboxylic acids do not directly participate as the carbonyl component in aldol condensations; the reaction involves aldehydes or ketones.
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