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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

Show two methods to synthesize each alkene: a one-step method using a Wittig reagent, and a two-step method that forms a carbon鈥揷arbon bond with an organometallic reagent in one of the steps.

a.

b.

What reagents are needed to convert each compound into butanal (CH3CH2CH2CHO )?

a.

b.

c.

Draw the products (including stereoisomers) formed when benzaldehyde (C6H5CHO) is treated with each Wittig reagent

a.

b.

Outline a synthesis of each Wittig reagent from Ph3P and an alkyl halide.

a.

b.

c.

What products are formed when each acetal is hydrolyzed with aqueous acid?

a.

b.
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