In this lab, the production of an amide from an amine was explored through the synthesis of acetaminophen from p-aminophenol. Acetominophen, a major metabolite of phenacetin, was first used clinically as a fever reducer by Von Mering in 1893. However, acetaminophen did not gain popularity until phenacetin and acetanilide had toxicity issues. Acetominophen was a significant discovery in clinical settings because of the increased safety of the drug compared to phenacetin and acetanilide. Today, acetominophen is used in Excedrin, Advil, and Tylenol as a pain reliever and a fever reducer. In the case of this lab, this compound represents a particularly useful example of using acetic anhydride to synthesize an amide from an amine. Some common uses…show more content… The acetic anhydride and water are added at the same time because as the acetic anhydride reacts with the p-aminophenol, intermediates are formed. Water is used to effectively stabilize these intermediates and catalyze the reaction. The stir bar and heat catalyze the reaction as well because they increase the rate of collision. The resulting contents of the round bottom flask after the p-aminophenol dissolved are shown in figure 1. During recrystallization, the round bottom flask is placed in an ice bath. This causes crystallization because it decreases the solubility of the acetaminophen. The crystals are then filtered out of the impurities and unreacted solvents via a filter flask. This resulted in white crystals as shown in figure 2 because of the removal of impurities and the creation of acetaminophen, which is white in color. After this, a TLC reading was obtained. The TLC reading allows the experimenter to see whether the product was different from the starting material, meaning that the reaction occurred. The results of the TLC plate are seen in figure 3. As shown, the product had a visible spot under UV light and the starting material had no visible spots. Therefore, product that was different than p-aminophenol was formed. Water was used to wash the crystals on the funnel because acetaminophen is insoluble in water so the water only removed impurities.…show more content… Although it is hard to see from this photo, there is a peak at 3160 cm-1, a peak at 3322 cm-1, and a peak at 1648 cm-1. The peaks at 3160 cm-1 and 3322 cm-1 are likely the alcohol stretch and the amide or amine stretch which would be found in both p-aminophenol and acetaminophen. However, this compound is likely acetaminophen due to the peak at 1648 cm-1, which is characteristic of a carbonyl stretch. The proton NMR reading affirms that the compound synthesized was acetaminophen. The integration shows 9 protons, which are found in acetaminophen. Additionally, there are 3 peaks for protons that do not interact with each other. This is characteristic of acetaminophen because of the alcohol, n-h group, and CH3 that is isolated. The ring is present as well in the NMR reading because of the 2 symmetric groups of 2 protons that interact with each other causing doublets on either side of the ring. Due to the combination of the TLC plate, IR reading, and NMR reading the product was
