In this discovery based experiment for the sophomore-level organic chemistry laboratory, students carry out a two-step synthesis of N,N-Diethyl-3-methylbenzamide (DEET) from 3-methylbenzonitrile rather than from the typical 3-methylbenzoic acid precursor. A hydrolysis reaction is first carried out on the nitrile functional group and this is followed by an alkylation reaction to produce DEET. Students are not told the outcome of the reactions in advance and must determine the identity of the intermediate and final products based on analysis of the physical and chemical properties of each. The experiment involves an alternative synthesis of a familiar compound and exposes students to concepts in nitrile and nucleophilic substitution reactions.

Synthesis of N,N-Diethyl-3-methylbenzamide (DEET) from an alternative starting material

248th National Meeting (2014)

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