19.5 Imine and Enamine Formation | Addition of Amines | Organic Chemistry

Chad provides a comprehensive lesson covering the formation of imines and Enamines.

Imine Formation
Imine formation is the result of the addition of primary amines to aldehydes and ketones. The reaction is reversible with H3O+ and is referred to as imine hydrolysis. This includes showing how the formation of hydrazones and oximes is analogous to the formation of imines with the use of hydrazine or hydroxylamine instead of a primary amine. The full imine formation mechanism is presented as well as a method for quickly and easily predicting the products of an imine hydrolysis reaction. Finally, the mechanism of the Wolff-Kishner reduction is included as well showing how it involves hydrazone formation.

Enamine Formation
Enamine formation is the result of the addition of secondary amines to aldehydes and ketones. The full enamine formation mechanism is also presented as well as a method for quickly and easily predicting the products of an imine hydrolysis reaction.

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00:00 Lesson Introduction
00:52 Formation of Imines (Addition of Primary Amines)
03:55 Mechanism of Imine Formation
11:08 Hydrolysis of Imines
12:43 Formation of Enamines (Addition of Secondary Amines)
14:09 Mechanism of Enamine Formation
19:18 Hydrolysis of Enamines
21:14 Mechanism of the Wolff-Kishner Reduction

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