MCAT Organic Chemistry Question 72: Answer and Explanation

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Question: 72

12. Treatment of this molecule with CrO₃ in aqueous H₂SO₄ in acetone will yield which of the following molecules?

A. 2-Phenylethanol
B. Phenylacetaldehyde
C. Phenylacetone
D. 2-Phenylethanoic acid

Correct Answer: D

Explanation:

This is the Jones oxidation, which will convert a primary alcohol into a carboxylic acid. Choice (A) is the original reacting molecule, and because the reaction will proceed, this is not correct. Because the reaction uses strong oxidizing agents, it won’t stop at the aldehyde, choice (B). This reaction also cannot make the ketone in choice (C) because it starts with a primary alcohol.

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