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Chapter 21: 22P (page 817)

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

a.

b.

c.

Short Answer

Expert verified

a.

b.

c

Step by step solution

01

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.

02

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
03

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

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