MCAT Organic Chemistry Question 78: Answer and Explanation

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Question: 78

3. What is the product of the reaction below?

  • A.
  • B.
  • C.
  • D.

Correct Answer: C

Explanation:

The reaction between a ketone and one equivalent of alcohol produces a hemiketal. This has an –OR group, an –OH group, and two alkyl groups attached at the same carbon. Choice (A) is a ketal, with two –OR groups and two –R groups. Choice (B) is a hemiacetal, with an –OH group, an –OR group, one R group, and a hydrogen atom. Choice (D) is a ketone. Note that a hemiketal is a very unstable compound, and will react rapidly with a second equivalent of alcohol to form a ketal in acidic conditions.

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