The active ingredient of the insect repellent Off is N, N...

The active ingredient of the insect repellent Off is $N, N$ -diethyl-m-toluamide, $m-\mathrm{CH}_{3} \mathrm{C}_{6} \mathrm{H}_{4} \mathrm{CON}\left(\mathrm{CH}_{2} \mathrm{CH}_{3}\right)_{2} .$ Outline a synthesis of this compound starting with 3 -methylbenzoic acid ( $m$ -toluic acid).

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Key Concepts

Amide Bond Formation via Nucleophilic Acyl Substitution

Once the acid chloride is generated, it can react with amines to yield amides. This reaction represents a nucleophilic acyl substitution mechanism, where the lone pair of electrons on the amine attacks the electrophilic carbonyl carbon of the acid chloride. The process involves the displacement of the chloride ion, leading to the formation of the amide bond. This methodology is widely used in organic synthesis for constructing compounds with the crucial amide functional group.

Acid Chloride Formation

This concept involves converting a carboxylic acid functional group into a more reactive acyl derivative, typically an acid chloride. Reagents such as thionyl chloride (SOCl2) are used because they transform the relatively unreactive carboxylic acid into an intermediate that can readily participate in further reactions, specifically nucleophilic acyl substitution. This step is essential in many synthesis routes where formation of a carbonyl derivative facilitates efficient reactions with nucleophiles.

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