MCAT Organic Chemistry Question 110: Answer and Explanation

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Question: 110

5. What is the final product of the following reaction?

A. CH₃(CH₂)₄CHO
B. CH₃(CH₂)₄COOH
C. CH₃(CH₂)₄CH₃
D. HOOC(CH₂)₄COOH

Correct Answer: B

Explanation:

Jones reagent (chromium trioxide in aqueous sulfuric acid) is an oxidizing agent. As such, it oxidizes primary alcohols directly to carboxylic acids. This reagent is too strong an oxidant to give an aldehyde, so choice (A) is incorrect; remember that pyridinium chlorochromate (PCC) is a common oxidizing agent used to convert alcohols to aldehydes without progressing to a carboxylic acid. Choice (D), a dicarboxylic acid, cannot form because there is no functional group on the other end of the molecule for the reagent to attack, and it cannot attack an inert alkane. Choice (C) represents reduction, not oxidation.

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