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4-Methylbenzoic Acid Lab Report

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In an extraction experiment, it is expected that the compounds which are soluble in water will be found in the aqueous layer, and those which are insoluble in water will be located in the organic layer. This is due to the differences in polarity with the bottom layer being more polar than the top. The compounds found in unknown five demonstrate this theory as the soluble 4-methylbenzoic acid was drawn off in the aqueous layer, while the benzil, which is insoluble, remained in the organic layer during extraction. The decrease in solubility that occurred in the aqueous solvent after deprotonation can be attributed to the increased solute-solute interactions and decreased solute-solvent interactions. Following the recrystallization process in this experiment, the melting points of each recovered compound was taken. The first compound, 4-methylbenzoic acid, was found to have a melting point of approximately 179.0 degrees Celsius. The literature value is 181 degrees Celsius showing that the melting point …show more content…

These results do not show the expected one to one ratio as the percent recoveries varied considerably. The extremely large percent recovery for 4-methylbenzoic acid actually would suggest that matter was created, however this is known to be an impossible feat. One possible source of error that could have led to this is not performing the vacuum filtration for long enough resulting in a small amount of liquid remaining with the crystals. If this filtration was performed for a slightly longer time interval, all of the liquid would have time to evaporate which would likely lower the percent yield. Another possible reason for the large percent recovery could be contamination of the aqueous phase while using the seperatory funnel. If small amounts of the organic phase was drained as well, this could increase the percent yield of the substance in the

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To go in more depth, 98.2% is a high yield, despite the inaccuracies due to time constraints, and the inability to the recrystallize the benzoic acid. As mentioned earlier, product might have been lost during the many filtration procedures in the experiment, as not all of the product was poured out from the flask, onto the filter. Since, recrystallization could not be done, the benzoic acid was immediately transferred onto the watch glass, and it is when transferring some product could have been left on the filter. Overall, pouring product into the filter, and trying to get every particle of product from the flask for each filtration procedure in the experiment, is rather difficult, and is impossible to get every bit of product. Another key possibility, though it fortunately did not occur in the experiment, a green, or purple result

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Therefore, using solely the melting point is not enough and therefore it is cannot be the only source to rely on. Another source of support to rely on is the thin layer chromatography to reinforce our hypothesis of the unknown. The data states that two compounds,

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