In the reaction mechanism, magnesium and anhydrous diethyl ether were added to bromobenzene (the limiting reagent). Adding the bromobenzene to the magnesium turnings quickly would form a biphenyl bi-product. Therefore, when added at the proper rate, this allowed magnesium to form a bond with bromine and with the alpha carbon that bromine was originally attached to. The magnesium then took the two electrons that it shared with the alpha carbon, making itself positively charged, and then detached itself from the molecule, creating a phenyl carbanion. The nucleophile then attacked the carbon on carbon dioxide, pushing the electron that the carbon shared with oxygen, onto the oxygen giving it a negative charge. Next, NaOH, HCl and water were added, the oxygen that carried the negative charge on benzoate, was protonated by the HCl. This formed the final product, benzoic acid and hydroxy magnesium bromide. In this reaction it is important to note that benzoic acid is not usually soluble in water, but deprotonating it tricks it into going into the aqueous layer. Also, we keep biphenyl (and the product) in the ether layer because biphenyl cannot be protonated or deprotonated. …show more content…
Table 2 also represents that the product was free of many impurities based on the narrow melting point range. According to Chemspider, benzoic acid will melt at 124°C. Therefore, the reason that the benzoic acid in this experiment started to melt at 118.8°C, was due to water being present in the final product. The reason that water was present in the final product was because the product was only dried for 20 minutes, therefore, the product was not completely dried. However, Figure 1 shows that the product obtained was white and fluffy, which represented that the product was relatively