The reaction of aldehydes and ketones with ammonia or 1º-amines forms imine derivatives, also known as Schiff bases (compounds having a C=N function). Water is eliminated in the reaction, which is acid-catalyzed and reversible in the same sense as acetal formation. The pH for reactions which form imine compounds must be carefully controlled. The rate at which these imine compounds are formed is generally greatest near a pH of 5, and drops at higher and lower pH’s. At high pH there will not be enough acid to protonate the OH in the intermediate to allow for removal as H₂O. At low pH most of the amine reactant will be tied up as its ammonium conjugate acid and will become non-nucleophilic.

Converting reactants to products simply

 

 Examples of imine forming reactions