Key Mechanism Formation of Imines

The mechanism of imine formation (Key Mechanism 18-5) begins with an acid-catalyzed nucleophilic addition of the amine to the carbonyl group. Attack by the amine, followed by deprotonation of the nitrogen atom, gives an unstable intermediate called a carbinolamine. 

This mechanism is more easily remembered by dividing it into two parts  

Acid-catalyzed addition of the amine to the carbonyl group. 

I Propose a mechanism for the hydrolysis of benzaldehyde methyl imine just shown. 

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