Question

Draw a stepwise mechanism for the following reaction

Short answer

The movement or shift or pi-electrons within a compound in order to increase the stability of the compound is referred as delocalization.

The lone pair of electrons delocalized as proton is abstracted by the double-bonded carbon atom.

Delocalization of pi-electrons of the substrate

Step-by-step solution

Delocalization

The movement or shift or pi-electrons within a compound in order to increase the stability of the compound is referred as delocalization.

The lone pair of electrons delocalized as proton is abstracted by the double-bonded carbon atom.

Delocalization of pi-electrons of the substrate

Resonance Structure

The cation is stabilized by resonance as the electrons shift back to the nitrogen atom and the nucleophilic attack of a water molecule form a new C-O bond.

Resonance stabilization

Deprotonation

The proton is removed to stabilize the ion.

Deprotonation

Protonation

The lone pair of electrons on nitrogen atom would abstract another proton giving a protonated amine.

Protonation

Stabilisation

The lone pair of electrons on the oxygen atom of the -OH bond shifts as the C-N bond breaks thereby stabilising the cation.

Stabilisation of the ion

Deprotonation

The proton leaves as the C=O double bond is formed.

Protonation

The amine group is protonated to form the required product,

Formation of the product