Nitration Of Methyl Benzoate Lab Report

The objective of this lab was to obtain a pure sample of methyl nitrobenzoate. This was done by performing a crystallization, vacuum filtration, and a recrystallization. Nitration is a commonly used reaction that involves an additional reaction that results in a resonance-stabilized intermediate that is later deprotonated to regenerate an aromatic ring. Because of methyl benzoate’s substituent, the nitro group is added in the meta position. The procedure included combining sulfuric acid, methyl benzoate, nitric acid, suction filtration, and purification through recrystallization. The recrystallized substance was then used to take the melting point determining how pure the crystals were. The reaction of methyl benzoate and nitric acid formed

Loss of product occurred due to multiple transfers between glassware and during both vacuum filtrations. During the first filtration, the mother liquor was cloudy signifying that crystals had gotten under the filter paper and were lost. Washing the crystals with methanol made the mother liquor even cloudier meaning that the methanol was warm enough to dissolve the desired product and impurities (337). The crystals formed after the recrystallisation were a bright yellow color due to the possible reaction of the methyl benzoate with the sulfuric acid. Once they were rinsed with methanol, the yellow color disappeared. Due to the loss of color, and therefore byproducts, it can be assumed the product was relatively pure. Due to the high sensitivity of the nitric acid, and how cautious one must be while using this acid, the process took much longer, and more steps had to be taken after the vacuum filtration to ensure all the acid was no longer in the product. The melting point of the crystals was 76.2-76.9°C, as compared to the accepted value of 78°C. The slight melting point depression revealed a slight