Video: EC17-18-S2-Q22

How can you obtain salicylic acid from aspirin? Write the chemical equation.

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Video Transcript

How can you obtain salicylic acid from aspirin? Write the chemical equation.

Before we go any further, we’re going to need to recall the structures of salicylic acid and aspirin. This is the structure of salicylic acid. And its formal name is two hydroxybenzoic acid. And this is the structure of aspirin, sometimes called two acetoxybenzoic acid.

What this question is asking for is a synthetic route from aspirin to salicylic acid. What we’re trying to achieve is the hydrolysis of an ester to remove this acetyl group. Ester hydrolysis is conventionally done in one of two ways. Both involve the treatment with water, but the catalyst is different. Either will use acidic conditions or basic conditions.

However, use of basic conditions will likely lead to the deprotonation of the carboxylic acid group, which will necessitate an acid workup stage in order to produce the salicylic acid. For this reason, I’m going to opt for using acid catalysis so that no extra workup step is needed.

This reaction generates our desired salicylic acid along with acetic acid. So here we’ve written the chemical equation that shows how you might obtain salicylic acid from aspirin.

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