Question

In: Chemistry

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

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

Solutions

Expert Solution

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.


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