P-Acetoluidide Lab Report

Part A- Preparation of p-Acetotoluidide
• After completing the experiment, a yield of 0.21 g of a pure white crystal were collected from the Buchner funnel, and when compared to the calculated theoretical yield, 0.82 g (found in Calculations 1.A), a percent yield of 25.4% can be calculated for this procedure. Although this value may not seem favorable for this procedure, when compared to the expected value described by the laboratory manual, which was 0.4 g, it can be seen that the procedure performed better than the current percent yield may illustrate. The most plausible reason for this expected value may be from the nature of the reaction performed here, the Fischer Esterification tends to act as an equilibrium, and as such it is prone
That said, the procedure still has a significant discrepancy in its yield that must be addressed. A noted the previously, the main observation that caused concern for this procedure came at the step where sodium bicarbonate was added to the solution in order to neutralize it; it was outlined that the sodium bicarbonate should have been added slowly, as well as while shaking. However, when performing this procedure, it is quite possible that the substance was added too quickly to the solution, and it is also equally possible that the solution was not shaken properly in order to avoid the over-addition of sodium bicarbonate. The failure to perform these steps correctly could have resulted in this loss of product due to the fact that too much base could have reacted with the product, resulting in a product that could have been washed by water, but
A simple solution for this issue could be the diligent performance of this procedure in general, therefore developing a calmer environment in which a substance can be added with care, (if extreme, it would also be possible to request the assistance of a peer in order to perform this step of the procedure adequately). Similarly, this would ameliorate the issue of not shaking the flask properly, due to the same reasoning. Even considering this issue, it can be said with some certainty that the quantity that was produced was indeed benzocaine; this conclusion stems from the fact that stock benzocaine has been described as having a white/colorless tint, as well as being ododrless2, characteristics that are shared with the product of this procedure. It is also unlikely that an influx of base would have caused an unknown product to form, due to the weak nature of sodium bicarbonate, which would alter the equilibrium more than the reaction itself. Therefore, although the procedure did not produce as much benzocaine as expected, even when accounting for the fact the reaction it is an equilibrium, the procedure still produced the desired product, as evidenced