Synthesis Of DEET
Synthesis of DEET
Abstract:
For this experiment m-toluic acid was reacted with thionyl chloride resulting in a nucleophilic acyl substitution which could then be used to create DEET with excess diethyl amine (Figure 1). This was done by adding diethyl amine drop wise using a seperatory funnel which resulted in a gas formation which was controlled with a condenser attached to a gas vacuum. The resulting mixture was then washed to remove excess acids and bases and rotovapped. DEET was synthesized from the experiment as NMR and IR data show strong peaks comparable to the literature values expected for DEET. The percent yield of the product at 56.1% could have been higher by adding more of the limiting reagent toluic acid.
Introduction:
In this experiment DEET is synthesized from m-toluic acid that has undergone a nucleophilic acyl substitution with thionyl chloride. The nucleophilic acyl substitution proceeds by having the carboxylic acid on m-toluic acid attack the thionyl chloride as a nucleophile1. Thionyl chloride then undergoes a loss of a leaving group as chlorine will leave1. The compound is then deprotonated from the free chlorine and SO2 is expelled as a gas as it is an excellent leaving group (Figure 2)1.
Diethyl amine can then be reacted with the compound via a nucleophilic attack. Once the amine is attached chlorine will leave as a leaving group as the carbonyl group reforms (Figure 3)1.
This provides a simple two-step process to attach a diethyl amine to a carboxylic acid to produce such compounds as DEET. Producing DEET is very helpful as it is a strong insecticide that affects a large array of different insects that other chemicals do not2. It is unknown how DEET exactly works but it is hypothesized that it blocks the receptors on insects causing them to be unable to find their hosts or prey2.
Discussion:
DEET was synthesized by first putting toluic acid into a round-bottom flask attached to a claisen adaptor with a seperatory funnel and
Abstract:
For this experiment m-toluic acid was reacted with thionyl chloride resulting in a nucleophilic acyl substitution which could then be used to create DEET with excess diethyl amine (Figure 1). This was done by adding diethyl amine drop wise using a seperatory funnel which resulted in a gas formation which was controlled with a condenser attached to a gas vacuum. The resulting mixture was then washed to remove excess acids and bases and rotovapped. DEET was synthesized from the experiment as NMR and IR data show strong peaks comparable to the literature values expected for DEET. The percent yield of the product at 56.1% could have been higher by adding more of the limiting reagent toluic acid.
Introduction:
In this experiment DEET is synthesized from m-toluic acid that has undergone a nucleophilic acyl substitution with thionyl chloride. The nucleophilic acyl substitution proceeds by having the carboxylic acid on m-toluic acid attack the thionyl chloride as a nucleophile1. Thionyl chloride then undergoes a loss of a leaving group as chlorine will leave1. The compound is then deprotonated from the free chlorine and SO2 is expelled as a gas as it is an excellent leaving group (Figure 2)1.
Diethyl amine can then be reacted with the compound via a nucleophilic attack. Once the amine is attached chlorine will leave as a leaving group as the carbonyl group reforms (Figure 3)1.
This provides a simple two-step process to attach a diethyl amine to a carboxylic acid to produce such compounds as DEET. Producing DEET is very helpful as it is a strong insecticide that affects a large array of different insects that other chemicals do not2. It is unknown how DEET exactly works but it is hypothesized that it blocks the receptors on insects causing them to be unable to find their hosts or prey2.
Discussion:
DEET was synthesized by first putting toluic acid into a round-bottom flask attached to a claisen adaptor with a seperatory funnel and