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During the Gabriel phthalimide synthesis of ethanamine, the reaction sequence proceeds via a specifiAmines Chemistry Question

Question

During the Gabriel phthalimide synthesis of ethanamine, the reaction sequence proceeds via a specific nucleophilic intermediate. What is the precise chemical identity of this active intermediate generated in the first step?

Answer: B

💡 Solution & Explanation

In the first step, phthalimide is reacted with ethanolic $KOH$. The base strictly abstracts the acidic $N-H$ proton situated between the two electron-withdrawing carbonyl groups, yielding the highly nucleophilic potassium phthalimide salt, which subsequently executes the $S_N2$ attack on the alkyl halide.

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