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Addition of Secondary Amines to Form Enamines

Most aldehydes and ketones react with 2º-amines to give products known as enamines. It should be noted that, like acetal formation, these are acid-catalyzed reversible reactions in which water is lost. Consequently, enamines are easily converted back to their carbonyl precursors by acid-catalyzed hydrolysis.

 

Mechanism

1) Nuleophilic attack

 

 

2) Proton transfer

 

 

3)  Protonation of OH

 

 

4)  Removal of water

 

 

5)  Deprotonation

 

 

Reversibility of Enamines

 

 

Example

Problems

1) Please draw the products for the following reactions.

 

 

2)  Please give the structure of the reactant needed to product the following product

 

 

Answers

1)

 

2)

 

 

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