Question

What carbonyl compound and amine are formed by the hydrolysis of each compound?

a.

b.

c.

Short answer

a.

b.

c.

Step-by-step solution

Hydrolysis of imines and enamines

Imines and enamines are hydrolyzed to form their corresponding carbonyl compounds in a reversible manner in the presence of an acid.

During the hydrolysis of enamines, the carbonyl carbon comes from the hybridized carbon bonded to the N atom.

Formation of carbonyl compound

Consider the hydrolysis of the given intermediates,

a. The hydrolysis of the given imine would give a molecule of benzaldehyde and cyclopentamine.

b. The hydrolysis of the given enamine would yield a molecule of cyclopentanone and N-methyl benzyl amine.

c. The hydrolysis of this intermediate gives N,N-dimethylamine and 2-methylpropanone.

Products

Hydrolysis of compound a.

The given enamine would give a molecule of cyclopentanone and N-methylbenzyl amine on hydrolysis.

Hydrolysis of compound b.

c. The given enamine would give a molecule of 2-methylpropanal and N,N-dimethylamine on hydrolysis.