MCAT Organic Chemistry Question 57: Answer and Explanation

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Question: 57

12. Treatment of (S)-2-bromobutane with sodium hydroxide results in the production of a compound with an (R) configuration. This reaction has most likely taken place through:

A. an S_N1 mechanism.
B. an S_N2 mechanism.
C. an S_N1 and S_N2 mechanism in sequence.
D. an S_N1 and S_N2 mechanism simultaneously.

Correct Answer: B

Explanation:

In this reaction, there has been an inversion of stereochemistry. The mostly likely explanation for this is that the reaction proceeded by an S_N2 reaction mechanism. Inversion of stereochemistry is a hallmark of S_N2 reactions, whereas racemization is a hallmark of S_N1 reactions.

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