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Chapter 21: Q-21-21-12P (page 699)

Question: How could you prepare the following amides using an acid chloride and an amine or ammonia?

  1. CH3CH2CONHCH3
  1. N,N-Dimethylbenzamide
  1. Propanamide

Short Answer

Expert verified

(a)

CH3CH2COCl+2CH3NH2→CH3CH2CONHCH3N-Methylpropanamide

(b)

(c)

CH3CH2COCl+NH3→CH3CH2CONH2Propanamide

Step by step solution

01

Nuclephilic acyl substitution

The given reactions are examples of nuclephilic acyl substitution reaction.

The leaving grops in teh acyl chlorides is chloride ion. They will be substituted by the nucleophiles.

02

Subpart (a)

The required chemical reaction n is given as:

CH3CH2COCl+2CH3NH2→CH3CH2CONHCH3\hfillN-Methylpropanamide

03

Subpart (b)

The chemical equation for the given reaction is as hown below:

04

Subpart (c)

The nucleophilic acyl substitution for the formation of the given product is as shown below:

CH3CH2COCl+NH3→CH3CH2CONH2Propanamide

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Most popular questions from this chapter

Treatment of 5- aminopentanoic acid DCC(dicyclohexylcarbodiimide) yields a lactam. Show the structure of the product and the mechanism of the reaction.

21-30 Electrostatic potential maps of a typical amide (acetamide) and an acyl azide (acetyl azide) are shown. Which of the two do you think is more reactive in nucleophilic acyl substitution reactions? Explain.

21-47 Draw and name compounds that meet the following descriptions:
(a) Three acid chlorides having the formulaC6H9ClO
(b) Three amides having the formula C7H11NO

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