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Magazine Chapter 20: Q9P (page 1038)
Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.
(a)N,N-dimethylacetamide
(b)acetanilide (PhNHCOCH3)
(c)cyclohexanecarboxamide
(d)
Short Answer
(a)
(b) 
(c)
(d)
Step by step solution
About the acetamide
(a) The acetic acid group attached to amide is called acetamide. This compound bears nitrogen and carbonyl groups. These compounds have a musty odor.
About N,N-dimethylacetamide
The acetamide that has two methyl groups at the nitrogen atom is N,N-diethylacetamide. The structure of this compound is given below.
About the reaction
The acyl chloride used is acetyl chloride and the amide used is dimethylamine. The resulting product will be N,N-dimethylacetamide. The by-product formed in this reaction is hydrochloric acid. The reaction is given below.
About acetanilide
(b) The organic compound that bears the benzene ring and group attached by NH bond is acetanilid. The structure of this compound is given below.
About the reaction
The acyl chloride used is acetyl chloride and the amide used is dimethylamine. The resulting product will beaniline. The by-product formed in this reaction is hydrochloric acid. The reaction is given below.
About cyclohexanecarboxamide
(c) The organic compound that bears benzene ring and group attached to bond cyclohexane is cyclohexanecarboxamide. The structure of this compound is given below.
About the reaction
The acyl chloride used is cyclohexanecarbonyl chloride.Ammonia isalso used. The resulting product will be cyclohexanecarboxamide. The by-product formed in this reaction is hydrochloric acid. The reaction is given below.
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