Topics: Chemical reaction, Nucleophilic substitution, Nucleophilic aromatic substitution Pages: 4 (1189 words) Published: October 16, 2010
The aim of the experiment is to assess the efficiency of the reaction between m-aminobenzoic acid and 2,4-dinitrochlorobenzene by determining the percent yield of the product, m-(2,4-dinitroanlino) benzoic acid. The reaction is an example of a nucleophilic aromatic substitution reaction, in which the nucleophile, m-aminobenzoic acid, attacks 2, 4-dinitrochlorobenzene resulting in the formation of the product. The extent of completion of the reaction was determined by calculating the percent yield of the reaction, which is a function of the affinity of the nucleophile to 2, 4-dinitrochlorobenzene. The more positive the overall charge on 2,4-dinitrochlorobenzene, as a result of electron withdrawing groups (EWG) on the molecule, the greater the attraction of the nucleophile, leading to a faster rate of reaction and greater percent yield of the final product. The ortha-para nitro groups on 2,4-dinitrochlorobenzne act as EWGs, thus increasing its overall positive charge and allowing it to react faster with the nucleophile. Upon completion of the endothermic reaction, the product was precipitated with deionized water, and vacuum filtration was used to collect solid m-(2, 4-dinitroanilino) benzoic acid from its liquid mixture. Recrystallization with boiling ethanol as the solvent was used to purify the product, as m-(2, 4-dinitroanilino) benzoic acid is soluble in ethanol while the impurities from the reaction are not. The final purified product was weighed, and its percent yield calculated in order to determine the extent of completion of the reaction.

25ml of colorless dimethylformamide (DMF) was added to a solid mixture containing 1.057g of beige 2, 4-dinitrochlorobenzene and 0.697g of copper colored m-aminobenzoic acid. An immediate copper colored mixture was observed, and the solution was heated using a water bath. Following 1.5 hours of heating, the mixture had turned a darker shade. The addition of 100ml of deionized water...
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