MCAT Organic Chemistry Question 137: Answer and Explanation

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Question: 137

2. Which of the following would be formed if methyl bromide were reacted with phthalimide and followed by hydrolysis with an aqueous base?

A. C₂H₅NH₂
B. CH₃NH₂
C. (C₂H₅)₃N
D. (CH₃)₄N⁺Br^–

Correct Answer: B

Explanation:

This reaction is similar to the Gabriel synthesis. Phthalimide acts as a nucleophile, the methyl carbon acts as an electrophile, and bromide acts as the leaving group. Therefore, the reaction between methyl bromide and phthalimide results in the formation of methyl phthalimide. Subsequent hydrolysis then yields methylamine.

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