The addition of heat and acid to 2-oxocyclopentanecarboxylic acid produces:

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Correct Answer: E. cyclopentanone
Beta-keto carboxylic acids undergo decarboxylation through ring formations. The carbonyl bond of the ketone will react with the alcohol group of the carboxylic acid to form a ring and release the carboxylic acid as CO2. The remaining enol will tautomerize into a carbonyl group again, leaving cyclopentanone. Notice a cyclopentaldehyde can’t even be a possible answer, aldehydes cannot exist in cyclo compounds.
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