Question

Draw the product formed when CH₃CH₂CH₂CH₂NH₂reacts with each carbonyl compound in the presence of mild acid.

a.

b.

c.

Short answer

a.

b.

c

Step-by-step solution

Imines

Imines are the compounds in organic chemistry containing a C-N double bond in which nitrogen can be bonded to a hydrogen atom or alkyl groups.

Mechanism of formation

• The nucleophilic attack of the amine at the carbonyl carbon
• The transfer of protons to form carbinolamine
• Protonation of the hydroxyl group
• Dehydration to form iminium ion
• Deprotonation to form the required imine

Product

a. Benzaldehyde reacts with butyl amine to form the corresponding imine:

Formation of N-butyl benzaldimine

b. The nucleophilic attack of carbonyl carbon of the acetone followed by dehydration and deprotonation gives the corresponding imine:

Formation of N-butyl propan-2-imine

c. Cyclohexanone reacts with the primary amines to give the corresponding imine:

Formation of N-butyl cyclopent-2-imine