The Synthesis Of Aspirin

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Medicine has evolved greatly, especially in terms of drugs, but one of the basics is aspirin, also referred to as acetylsalicylic acid. There are many different reactions that can be conducted in order to synthesize aspirin. One way being the Fischer esterification, which is a reaction between an alcohol and a carboxylic acid within the presence of a catalyst, synthesizing an ester (Weldegirma, 2014). The catalyst has to be something that will provide the addition of a proton, such as a Lewis acid, in order to provide a more reactive electrophile and speed up the reaction (Fischer Esterification Fischer-Speier Esterification, 2015). Some possibilities for the catalyst are sulfuric acid, tosic acid, and phosphoric acid (James, 2014). For the …show more content…
Also, when looking at the IR spectrum on can see that it I very erratic and ridged, which makes it difficult to interpret. The state of the IR spectrum could be due to the fact that the sample that was tested was impure. However, in order to indicate that the final product of aspirin is present on would look for a carbonyl peak at approximately 1700 cm-1. Although this is not present one can say that the initial product of salicylic acid in not present because the lack of a broad peak around 3300 cm-1, which would indicate an alcohol. As for the TLC, this helped determine that aspirin was produce because the initial TLC showed two dots, which indicated the starting materials. The second TLC only had one dot and it had dropped a bit, which indicated the final product and the third TLC also showed one dot, supporting the second TLC. There is also a 13C NMR and this helps identify the product because the number of peaks that are present. Each peak represents a different unique carbon in a compound and in aspirin there are 9 so that mean 9 peaks should be present and there is. Also the carbon that is double bonded to the oxygen in the added acetyl group of the aspirin should have a peak at approximately 170-178 ppm, which is present. In addition, there was also a 1H NMR and this helped identify the product because the hydrogen’s of the methyl group appeared at approximately 2.5 ppm, the hydrogen’s connected to the ring appeared between 7.2-8 ppm, and the hydrogen connected to the oxygen appeared just after 8 ppm. This data helped verify that aspirin was synthesized. As for the questions in the lab manual there are 4 sets of peaks starting from left to right the first peak represents hydrogen 7, the second peak represents hydrogen 5, the third peak is hydrogen 6, and the fourth peak represents hydrogen 4. For question 2, if salicylic acid and acetylsalicylic acid were 1:1 ratio the 1H NMR would remain the same

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