Question

What compound is formed when salicaldehyde is mixed with methylamine in a Schiff’s base condensation reaction?

Answer 1

When salicaldehyde is mixed with methylamine it forms an imine (Schiff’s base)

In this reaction C=O group is replaced by C=N-R group. It is usually formed by condensation of an aldehyde or ketone with a primary amine according to the following given mechanism.

The electrophilic carbon atom of salicaldehyde will be targets of nucleophilic attack by methylamine. The end result of this reaction is a compound in which the C=O double bond is replaced by a C=N double bond. This type of compound is known as an imine, or Schiff base.

CH₃NH₂ initially attack the carbonyl carbon, followed by hydrogen transfers to give an amine where the nitrogen is bonded to a carbon that also contains a hydroxy group. Under acidic conditions, the hydroxyl group is protonated, followed by loss of water to give the Schiff base.