24. Enolate Chemistry: Reactions at the Alpha-Carbon
Enamine Alkylation and Acylation
7:39 minutes
Problem 22.7
Textbook Question
Textbook QuestionWithout looking back, propose a mechanism for
the hydrolysis of this iminium salt to the alkylated ketone.
The first step is attack by water, followed by loss of a proton to give a carbinolamine. Protonation on nitrogen allows
pyrrolidine to leave, giving the protonated ketone.
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