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Chapter 21: 22P (page 817)

顿谤补飞鈥倀丑别鈥俻谤辞诲耻肠迟鈥俧辞谤尘别诲鈥倃丑别苍鈥侰贬3CH2CH2CH2NH2reacts 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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Most popular questions from this chapter

Draw a stepwise mechanism for each reaction.

a.

b.

Draw a stepwise mechanism for the following reaction

The boiling point of butan-2-one ( 79.64oC ) is significantly higher than the boiling point of diethyl ether ( 34.6OC), even though both compounds exhibit dipole鈥揹ipole interactions and have comparable molecular weights. Offer an explanation.

Explain why benzaldehyde is less reactive than cyclohexanecarbaldehyde towards nucleophilic attack.

Use the 1 H NMR and IR data to determine the structure of each compound.
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