Condensation Synthesis Of Aspirin

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Aspirin is a very well known, versatile, cheap and easy to produce pain reliever available today. Not only can Aspirin be used to treat pain, fever and inflammation, but it can also decrease the risk of heart attacks, strokes and blood clots (Wikipedia, 2017). The world currently consumes an estimated amount of 40,000 tonnes of Aspirin per year and demand is only growing. The first recorded use of Aspirin was over 2,400 years ago, in the form of leaves, bark or flowers from the willow tree (Wikipedia, 2017). The only problem with consuming this organic compound was that it had a large pH level causing irritation to the mouth, throat and stomach, usually causing more harm than good. Salicylic acid was not a viable pain reliever until the synthesis …show more content…

A condensation reaction is a reaction where two molecules react to form a larger and smaller molecule (Boundless 2016). A type of condensation reaction is an esterification reaction generally when an alcohol reacts with a carboxylic acid. However, esters can also be created from phenols but requires a vigorous ethanoylating agent such as an anhydride (York, 2000). In the synthesis of aspirin, the phenol mentioned is salicylic acid. The structure of a basic phenol is shown in figure 3 and figure 4 shows the structure of salicylic acid where the phenol group can easily be seen. The required anhydride for the reaction is acetic anhydride. Similarly, figure 6 shows the general structure of an anhydride and figure 5 shows the structure of acetic anhydride. It can be clearly seen that the basic structure of an anhydride is present in acetic anhydride. Therefore, the phenol molecule of the reaction is salicylic acid and the anhydride is acetic anhydride, reacting together to produce the ester of acetylsalicylic acid. The structure of acetylsalicylic acid is shown in figure 7, a combination of a phenol and one side of the anhydride. The other side of the anhydride is the second product which is acetic acid; a by-product of the …show more content…

In terms of aspirin, the forward reaction is forming Aspirin and the reverse forming the reactants. A system like this will reach a point called chemical equilibria. Temperatures effect on equilibrium can be explained by Le Chatelier’s principle (Wikipedia 2017). Le Chatelier’s principle states that when a system in equilibrium is subjected to a change, the system readjusts itself to counteract the applied change. In terms of Aspirin, when the temperature is changed, the system will adjust itself to counteract the change. Figure 8: Synthesis of aspirin reaction. (Chemskills, 2014) As shown in figure 8, the synthesis of Aspirin reaction contains salicylic acid and acetic anhydride (a phenol and an anhydride) to form acetylsalicylic acid and acetic acid (The product and by-product). The chemical equation for the equation is: C_7 H_6 O_3+C_4 H_6 O_3 + Energy ↔C_9 H_8 O_4+C_2 H_4 O_2 (ΔH =

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