N-Diethylamine Lab Report

In the first step of the experiment, m-toluic acid reacted with thionyl chloride to form the acid chloride derivative of m-toluic acid. In this reaction, the carboxylic acid is first converted into an acyl chlorosulfite intermediate, replacing the –OH of the acid with a better leaving group. The acyl chlorosulfite then reacts with a nucleophilic chloride ion, at which point the chlorosulfite leaves in the form of sulfur dioxide and chloride ion. The remaining acid chloride then reacts with diethylamine. Diethylamine is used in excess to neutralize the hydrogen chloride produced in the reaction. The lone pair of electrons on the nitrogen atom performs a nucleophilic attack on the carbonyl carbon, while a pair of electrons in the double bond is pushed to the oxygen atom. When an electron pair from the oxygen atom restores the double bond, the chloride ion will act as a leaving group. The nitrogen atom is deprotonated by a chloride atom, forming N,N-diethyl-m-toluamide. One interesting note is that after the addition of thionyl chloride and pyridine to m-toluic acid, an evolution of gases was observed along with a color change inside the reaction mixture. The …show more content…
Companies manufacturing this product would need N,N-diethyl-m-toluamide in large quantities for mass production. Studying and understanding this mechanism is important in order to develop the most efficient means for producing high quality and high yield of N,N-diethyl-m-toluamide. Studying the structure of N,N-diethyl-m-toluamide in relation to its effectiveness may also lead to new insights into developing safer skin products. The synthesis of N,N-diethyl-m-toluamide will be important for as long as this chemical compound is used in insect repellent products, which makes it necessary to study the reaction mechanism and find ways to increase purity and percent yield of the