Question

Draw a stepwise mechanism for the following imine hydrolysis

Short answer

The acidic hydrolysis of imine would give the corresponding carbonyl compound. The mechanism of hydrolysis involves protonation, nucleophilic attack, and proton transfer.

The mechanism of imine hydrolysis is briefly discussed. The imine is protonated to form the iminium ion.

Formation of iminium ion

Step-by-step solution

Imine hydrolysis

The acidic hydrolysis of imine would give the corresponding carbonyl compound. The mechanism of hydrolysis involves protonation, nucleophilic attack, and proton transfer.

The mechanism of imine hydrolysis is briefly discussed. The imine is protonated to form the iminium ion.

Formation of iminium ion

Nucleophilic attack

The water molecule would attack the electrophilic iminium ion to form a C-O bond.

Nucleophilic attack

Proton transfer

The proton of the oxygen atom would donate a pair of electrons and bond to the electrophilic nitrogen atom.

Transfer of proton

Protonation

The nitrogen atom would abstract another proton cleaving the C-N bond.

The proton donates a pair of electrons, and the required product would be formed.

Proton Transfer