Question

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

(b)

(c)

Short answer

(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 $\text{HN}{\left({\text{CH}}_2{\text{CH}}_3\right)}_2$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 $\text{HN}{\left({\text{CH}}_2{\text{CH}}_3\right)}_2$, a carboxylate anion is formed and, on heating, ${\text{COO}}^{-}$is converted to${\text{CONEt}}_2$ . 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.

Reaction of N, N-dimethylformamide(DMF)