Before the advent of Advil and Tylenol, did people simply have to “grin and bear

Question

Before the advent of Advil and Tylenol, did people simply have to “grin and bear it” when it came to pain? One of the most common ancient medicines for pain, fever, and inflammation came as a byproduct of the willow tree. While the first uses date back to 400 BCE, American historians cite the use of willow bark tea by the Lewis and Clark exploration party in the early 1800’s. Salicylic acid derived from the willow tree’s bark was the key chemical involved with the relief of pain and the reaction to make aspirin is a fairly simple one performed in numerous chemistry classrooms nationwide. Aspirin can be made by reacting acetic anhydride (C4H6O3) with salicylic acid (C7H6O3) to form aspirin (C9H8O4). C4H6O3 + C7H6O3 --> C2H4O2 + C9H8O4 When synthesizing aspirin, a student began with 3.05 mL of acetic anhydride (density = 1.08 g/mL) and 1.85 g of salicylic acid. The reaction was allowed to run its course and 1.84 grams of aspirin was collected by the student. Determine the limiting reactant, theoretical yield of aspirin, and percent yield for the reaction.

Explanation / Answer

moles of salicylic acid = 1.85 g/138.121 g/mol = 0.013 mols

moles of acetic anhydride = 3.05 ml x 1.08 g/ml/102.09 g/mol = 0.032 mols

Since moles of salcylic acid is lower, this is the limiting reagent in the reaction.

Theoretical yield of aspirin = 0.013 mols x 180.157 g/mol = 2.34 g

Percent yield of reaction = 1.84 x 100/2.34 = 78.63%

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