MCAT Organic Chemistry Question 93: Answer and Explanation

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Question: 93

3. Which of the following reactions would produce the compound below?

  • A. CH3CHO + CH3CH2CH2CHO →
  • B. CH3COCH3 + CH3CH2CH2CHO →
  • C. CH3CH2COCH3 + CH3CHO →
  • D. CH3CH2CHO + CH3CH2CHO →

Correct Answer: D

Explanation:

The reactions listed in the answer choices are examples of aldol condensations. In the presence of a base, the α-hydrogen is abstracted from an aldehyde, forming an enolate ion, [CH3CHCHO]. This enolate ion then attacks the carbonyl group of the other aldehyde molecule, CH3CH2CHO, forming the pictured aldol.

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