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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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Most popular questions from this chapter

Two naturally occurring compounds that contain stable cyclic hemiacetals and acetals are monensin and digoxin, the chapter-opening molecule. Monensin, a polyether antibiotic produced by Streptomyces cinamonensis,is used as an additive in cattle feed. Digoxin is a widely prescribedcardiac drug used to increase the force of heart contractions. Label each acetal, hemiacetal, and ether in both compounds.

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

a.

b.

An unknown compound C of molecular formula C6H12O3 exhibits a strong absorption in its IR spectrum at 1718 cm-1 and the given 1H NMR spectrum. What is the structure of C?

Which compound in each pair forms the higher percentage of gem-diol at equilibrium?

a.

or

b.

or

Draw the products of the following Wittig reactions

a.

b.
See all solutions

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