Chapter 20: Q18P a. (page 1065)

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.
(a)
(b)
(c)

Short Answer

Expert verified

(a)

(b)

(c)

Step by step solution

Amines and carboxylic acids

Amines are compounds containing the -NH₂group and carboxylic compounds with the –COOH group.Different reagents are used to prepare acid derivatives, such as amide $HN {({CH}_{2} {CH}_{3})}_{2}$ is used. The formation of amide by using industrial methods needs high temperature.

Synthesis of N, N-diethyl-meta-toluamide

(a) When 3-methyl benzoic acid is treated with $HN {({CH}_{2} {CH}_{3})}_{2}$ , a carboxylate anion is formed and, on heating, ${COO}^{-}$ is converted to ${CONEt}_{2}$ . The product created is N, N-diethyl-meta-toluamide.

Synthesis of N, N-diethyl-meta-toluamide

Synthesis of acetanilide

(b) When aniline is treated with acetic acid , an acetate ion is formed along with a phenyl ammonium ion. Further, on heating, acetanilide is formed.

Reaction of acetanilide

Synthesis of acetanilide

Synthesis of N, N-dimethylformamide(DMF)

(c) When aniline is treated with acetic acid (CH₃COOH) , an acetate ion is formed along with a phenyl ammonium ion. Further, on heating, acetanilide is formed.