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)

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)

(a)

(b) 
(c)

(d)

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Question: Phenols are less acidic than carboxylic acids, with values of around 10. Phenols are deprotonated by (and therefore soluble in) solutions of sodium hydroxide but not by solutions of sodium bicarbonate. Explain how you would use extractions to isolate the three pure compounds from a mixture of p-cresol (p-methylphenol), cyclohexanone, and benzoic acid.
Predict the productsand propose mechanisms for the following reactions.

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.
Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.
(a) methyl salicylate
(b) methyl formate (bp 32C)
(c) ethyl phenylacetate
Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.
(a)methyl salicylate
(b) methyl formate
(c) ethyl phenylacetate
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