How do you draw keto-enol tautomerization and enamine tautomerization mechanisms?

1 Answer
Truong-Son N.
Nov 19, 2015

I will examine the keto-enol tautomerization. You can analogize with the imine-enamine tautomerization.

We have acidic and basic conditions. Below, the left side will be acidic conditions, and the right side will be the basic conditions.

When you analogize, notice that enamines are very similar to enolates, and imines are very similar to ketones. Here is an example of acetone vs. a pyrrolidine enamine:

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