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Provide a detailed mechanism that rationalizes the transformation outlined below....

Question:

Provide a detailed mechanism that rationalizes the transformation outlined below.

Iminium ions as carbon electrophiles:

The reaction between an amine and aldehyde such as formaldehyde gives an iminium ion. The carbon of the iminium ion acts as an electrophile. Iminium ions will react with an enolate to form new carbon-carbon bond

Answer and Explanation:

The mechanism is given below:

This is a variation of the Mannich reaction:

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Aldehydes & Ketones: Reaction Mechanisms
Aldehydes & Ketones: Reaction Mechanisms

from AQA A-Level Chemistry: Practice and Study Guide

Chapter 15 / Lesson 1
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