MCAT Organic Chemistry Question 106: Answer and Explanation

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Question: 106

1. Which of these compounds would be expected to decarboxylate when heated?

  • A.
  • B.
  • C.
  • D.

Correct Answer: D

Explanation:

This compound is a β-keto acid: a carbonyl functional group at the β-position from a carboxyl group. Decarboxylation occurs with β-keto acids and β-dicarboxylic acids because they can form a cyclic transition state that permits simultaneous hydrogen transfer and loss of carbon dioxide. Choice (B) is a diketone and does not have a single carboxyl group. Choices (A) and (C) are γ- and δ-dicarboxylic acids, respectively, and can decarboxylate but with more difficulty.

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