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The following experiment synthesized N,N'-diethyl-3-benzamide from m-toluic acid. Initially, 2.5 g of m-toluic acid and 2.0...

The following experiment synthesized N,N'-diethyl-3-benzamide from m-toluic acid. Initially, 2.5 g of m-toluic acid and 2.0 mL of thionyl chloride are heated for a period of time. Then 30 mL of anhydrous ether was added to the mixture. 10 mL of anhydrous dry ether and 5.0 mL of diethylamine were added dropwise over a period of 10 minutes using a separatory funnel. After that, 15 mL of 2.5 M sodium hydroxide were added dropwise using a separatory funnel. Then the ether layer was separated and washed with 15 mL of cold 3M hydrochloric acid and then with 15 mL of water. Then a chromotography column was packed with 15 g of activated alumina and petroleum ether as the solvent. DEET ran through the column and was collected and then evaporated to remove the petroleum ether.

Propose a step-wise, arrow-pushing mechanism for the synthesis of DEET.

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