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Synthesis of Aspirin

1. Draw the structures of salicylic acid and aspirin. Circle and identify the functional groups present in each compound.

3. Sulfuric acid is a catalyst. What does that mean?

5. What safety, environmental and economic considerations would be important to a company manufacturing 1 million pounds of aspirin each year by this procedure? Which ones do you think are most important? Why?

6. The aspirin synthesized in a home experiment should never be taken home for medicinal use. Why not?

Solution Preview

Aspirin is most widely sold over-the-counter drug. It has the ability to reduce fever (an antipyretic), to reduce pain (an analgesic), and to reduce swelling, soreness, and redness (an anti-inflammatory agent). One of the first recorded accounts for the discovery of aspirin appeared in England, in 1763, crediting the bark of willow trees with a beneficial effect in alleviating distress due to fevers, aches, and pains. Later, the compound salicylic acid (named for the Latin word for willow, salix) was isolated from willow bark. It proved to be the active ingredient. By 1860, organic chemists were able to synthesize salicylic acid from basic starting materials, this furthered the therapeutic use of the substance, but there were problems. Salicylic acid proved to be irritating to the membranes of the throat, mouth, and stomach. These problems are directly associated with the high acidity of the compound, but a simple remedy was discovered, namely, replacement of the acidic phenolic hydrogen atom with an acetyl group.

3. Sulfuric acid is a catalyst. What does that mean?

The reaction for the preparation of aspirin from salicylic acid and acitic anhydride is an esterification reaction. It requires an acid (H+) catalyst to proceed the reaction. Sulfuric acid is an acid, and being used as a catalyst means that its ...

Solution Summary

Aspirin is most widely sold over-the-counter drug. It has the ability to reduce fever (an antipyretic), to reduce pain (an analgesic), and to reduce swelling, soreness, and redness.

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