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OFF, an Insect Repellant

The first step in order to synthesize OFF is by performing the reaction of the m-toluic
acid with the thionyl chloride. M-toluic acid has a high melting point that is why it is solid in
room temperature while thionyl chloride is a liquid which is usually used to convert the
carboxylic acids into their acid chloride derivatives. The reason why thionyl chloride can convert
acids into their acid chloride derivatives is because it is highly reactive. The S=O bond is highly
polarized and is analogous to the carbonyl bond. Also, the partial positive charge on the S is
susceptible to a nucleophilic attack. After the formation of an intermediate and removal of
proton, the result of the first-step of the reaction is the conversion of the poor leaving group (-
OH) into a good leaving group. The next reaction is to form the N, N-dimethyl toluamide by
reacting it with the acid chloride formed from the first reaction, with diethylamine. Diethylamine
is a good nucleophile and the carbonyl group is nicely polarized but the reason why it is not
advisable in this reaction to perform a reaction of carboxylic acid and diethylamine is because
the result of acid-base chemistry is a salt. In this second step of the reaction, the chloride anion
acts as the nucleophile. The chloride attack leads to a mini chain reaction which results in the
elimination of sulfur dioxide and hydrogen chloride. The acid chloride formed is much more
reactive than the carboxylic acid because chloride is a better leaving group. In reaction with the
acid chloride, the diethylamine acts as the nucleophile and attack at the partial positive charge of
the carbon of the acid chloride. A tetrahedral intermediate will then form. Then, the formation of
the C=O bond pushes out the best leaving group which is the chloride to form the N, N-dimethyl
toluamide.
During the work-up procedure, several extractions were made to get the desired product.
The first and second extraction procedure involves the addition of 5% aqueous NaOH to the
mixture to allow the layers to separate into two layers; top layer which contains the ether solution
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and the desired product (organic layer), and the bottom layer which contains the aqueous layer.
The aqueous layer which is composed of unreacted m-toluic acid, traces of HCl, unreacted m-
toluic acid chloride, diethylamine, and NaCl are separated from the top layer and most of it were
removed from the organic layer of the solution. Then, 2 mL of 10% HCl aqueous solution was
then used to react with any remaining diethylamine to form hydrochloride salt which is also then
removed, by extracting the aqueous layer and leaving the organic layer. 2 mL of water was then
added to extract the remaining diethylamine hydrochloride, and remaining thionyl chloride.
Sodium sulfate, a drying agent which is used in acidic conditions, was then added so that the
ether solution that contains the desired product, N, N-diethyl toluamide, will turn clear and the
desired product will be more pure.
According to the IR spectra of the product obtained from the experiment, its IR spectrum
successfully identified the important peaks such as: phenyl group at ~1630.01

, amide peak
at ~1462.64

, carboxylic acid ketone at ~1762.35

, ether peak at ~1241.00

, and
the IR card/alkanes at ~2852.33

to ~2916.83

. The IR spectrum of the product

doesnt contain any OH peak which means that the product obtained is a pure N, N-diethyl
toluamide because it doesnt contain any alcohol nor water contamination. With the IR spectra
obtained and the important peaks identified, the synthesized product is no doubt going to work as
a mosquito repellant, OFF.





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References
Bruice, P. Organic Chemistry, 7
th
ed.; Pearson: New Jersey, 2013.
Padias, A. Making The Connections, 2nd ed.; Hayden-McNeil Publishing: Plymouth, MI, 2013.
Padias, A. Organic Chemistry Laboratory Manual, 4th ed.; Hayden-McNeil Publishing:
Plymouth, MI, 2013.