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How do you account for the smell of vinegar when an old bottle of aspirin is opened?

How do you account for the smell of vinegar when an old bottle of aspirin is opened?

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Answer #1

Over time, aspirin (an ester) can be hydrolyzed by H2O that contaminates the container. The hydrolysis products of aspirin are salicylic acid and acetic acid.

Vinegar is made of dilute acetic acid. This hydrolysis product therefore gives the vinegar smell to an old aspirin bottle.

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