M-Toluamide Synthesis Lab Report

In the reaction mechanism, a carboxylic acid, m-toluic acid is used to synthesize N,N-diethyl-m-toluamide, also know as DEET, through a nucleophilic acyl substitution reaction. The reaction begins by first converting the m-toluic carboxylic acid into an acyl chlorosulfite through a reaction using thionyl chloride. The carboxylic acid is converted into an acyl chloride because the acyl chloride is more reactive. In this step, hydrochloric acid is formed from a hydrogen on the carboxylic acid and a chlorine from the thionyl chloride atoms binding together. A chlorine atom then attaches itself to a double bonded oxygen on the acyl chlorosulfite, kicking the double bonded oxygen’s electrons up making it negatively charged. The negatively charged
Figure 1 depicts an IR spectrum for the product synthesized. An IR spectrum demonstrates peaks for specific functional groups, which are present in the final purified product. Table 2 is a representation of important peaks in Figure 1 and demonstrates there was a peak present in the IR spectrums wavelength at 1738 cm^(-1). This peak ultimately depicts a carbonyl group based off of an carbonyl group’s wavelength ranging from 1750-1705 cm^(-1). According to Webbook.nist, the literature IR spectrum of N,N-diethyl-toluamide has a peak at about 1730 cm^(-1), therefore, depicting an carbonyl functional group. Table 2 also demonstrates a peak was present at 1583 cm^(-1), this peak represents an aromatic ring being present in the molecule due to an aromatic ring’s literature value ranging from 1600-1475 cm^(-1). N,N-diethyl-toluamide’s literature IR spectrum has a peak at approximately 1475 cm^(-1), therefore, representing an aromatic ring (Webbook.nist). Table 2 also exemplifies a peak was present at 2943 and 2970 cm^(-1). Alkanes have a literature range ranging from 3000-2800 cm^(-1), therefore, these two peaks are representing alkanes present in the molecule. The literature IR spectrum of N,N-diethyl-m-toluamide has two peaks at approximately 2970 and 2950 cm^(-1), representing alkanes (Webbook.nist).
Another way to improve this procedure would be to add a second 15 mL portion of NaCl to the separatory funnel to make sure the aqueous layer was fully removed. Additionally, column chromatography could have been used in this procedure in order to purify the product. To further improve this procedure; a color change titration technique could have been used in order to quickly determine if the product was formed before running an