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How do primary amines react with aldehydes to form imines?
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aldehyde
Alcohols may be oxidized to give aldehydes, ketones, and carboxylic acids. The oxidation of organic compounds generally increases the number of bonds from carbon to oxygen, and it may decrease the number of bonds to hydrogen.
Primary amines react readily with aldehydes to form imines, which are also known as azomethines or Schiff bases.12
The process is a form of nucleophilic addition where the amine acts as a powerful nucleophile that attacks the carbonyl group of the aldehyde. The reaction proceeds through an initial addition product, which then undergoes the loss of a water molecule to yield the final imine, characterized by a carbon-nitrogen double bond ().2
While primary amines react readily in this manner, the stability of the resulting imines varies; they are generally stable only if at least one of the R groups attached to the carbon or nitrogen is an aromatic ring. In other cases, the imines may rapidly polymerize.2