110k views
1 vote
What happens when an aldehyde or ketone is treated with a primary amine?

User Tormod
by
7.4k points

1 Answer

3 votes

Final answer:

When an aldehyde or ketone is treated with a primary amine, an imine is typically formed through a condensation reaction involving the nucleophilic attack of the amine on the carbonyl group and subsequent dehydration.

Step-by-step explanation:

Reaction of Aldehydes and Ketones with Primary Amines

When an aldehyde or ketone is treated with a primary amine, an imine is often formed. The reaction involves the nucleophilic attack of the primary amine on the carbonyl carbon of the aldehyde or ketone, followed by a series of proton transfers and the loss of water. This process is also known as a condensation reaction because it involves the joining of two molecules with the elimination of water.

General Mechanism

The general mechanism for this reaction begins with the nucleophilic primary amine attacking the electrophilic carbon of the carbonyl group in the aldehyde or ketone. A carbinolamine intermediate is formed, which then undergoes a dehydration step to yield the imine and water as a by-product.

Amide Formation

It's important to note that when a carboxylic acid reacts with primary amines, different chemistry occurs leading to the formation of amides rather than imines. In both cases though, whether we're dealing with the reaction of aldehydes/ketones or carboxylic acids with primary amines, water is formed as a by-product.

The information given on the oxidation of alcohols, the formation of glycosidic bonds, and the generation of enolates while insightful, is not directly related to the specific question at hand about primary amines reacting with aldehydes or ketones.

User Vich
by
7.8k points