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Willow Bark

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Organic Chemistry Research Assignment (Pg. 77 #53)
The Structure of Aspirin and its Relation to Willow Bark
Question:
Acetylsalicylic acid (ASA), better known as Aspirin, is a common pain reliver. Research the following topics:
- Explore the chemical reactions associated with the synthesis of ASA, Determine the type of reaction that occurs, and the class of organic compounds involved.
- Research the historical connection between willow bark and ASA. What advantages does ASA have over the compound extracted from willow bark? How were these advantages achieved?
Introduction:
Aspirin, otherwise known as acetylsalicylic acid is a common over the counter medication which is used to reduce fever and relieve moderate pains. In lower doses it may also …show more content…
Specifically, the hydrogen (H) of the hydroxyl group on the salicylic acid is exchanged with an acyl (RCO–) group from acetic anhydride. The result forms an ester on the salicylic acid which changes the molecule to acetylsalicylic acid or aspirin. The result also creates a carboxylic acid group on the acetic anhydride which transforms it into acetic acid.

This reaction can also be classified as an acid esterification. This means that an ester group is created with the use of acid. In the case of this reaction, the phosphoric acid catalyst was responsible. The catalyst promoted the cleavage of the hydrogen ion from the salicylic acid, which prompted the replacement by the acyl group from acetic anhydride.

Post-Reaction:
After the reaction, water is added to isolate the aspirin. However, this aspirin may be a crude product due to remaining salicylic acid that may be present. To determine impurity of the sample, heat can be used to test the melting point of the crude aspirin. The melting point of pure aspirin is 138-140 C and the melting point of salicylic acid is 158-161 C. If there are impurities, the melting point range for the aspirin will be lower than the range of pure aspirin. If deemed required, the product can be purified through the recrystallization of the crude product in hot …show more content…
This irritation included nausea, vomiting, bleeding, and ulcers caused due to the acidic properties of salicylic acid. To counteract this issue, Felix Hoffman created a buffering system by modifying the hydroxyl group on the benzene ring of salicylic acid. This new molecule caused less gastrointestinal stress and was called acetylsalicylic acid. This new molecule was still converted back to salicylic acid in the blood and stomach which means it still yielded the same benefits.
Essentially, Hoffman had created a delivery system for salicylic acid which allowed patients to consume greater amounts with less of the negative side effects. This new molecule is what we call aspirin and it still works in the same way as it did since its discovery. However, even modern-day aspirin can cause the same problems in unregulated or high doses, so it should still be used with caution.
The method by which this advantage was created was through the reaction that is outlined above. Essentially an acyl group was added to the salicylic acid which reduced its negative effects on the gastrointestinal system of those who consumed it, while retaining its positive effects as

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