24Aspirin - Reminder: These notes are meant to supplement,...

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Reminder: These notes are meant to supplement, not replace, the textbook and laboratory manual. Synthesis of Aspirin 1. Here is a balanced equation for the synthesis of aspirin: O | | + CH 3 COH CO 2 H OH O O | | | | CH 3 —C—O—C—CH 3 + CO 2 H O | | O—C—CH 3 salicylic acid acetic acid acetic anhydride aspirin H 3 PO 4 Functional groups involved: Salicylic acid is both a carboxylic acid and a phenol. Acetic anhydride is an anhydride. Aspirin is a carboxylic acid and an ester. Acetic acid is a carboxylic acid. * The mechanism of this reaction is: O | | + CH 3 COH CO 2 H OH HO O | | | | CH 3 —C—O—C—CH 3 + CO 2 H OH | | O—C—CH 3 O O | | | | CH 3 —C—O—C—CH 3 H 3 PO 4 + H 2 PO 4 + HO O | | | | CH 3 —C—O—C—CH 3 CO 2 H OH O | | | O—C—O—C—CH 3 | | H CH 3 CO 2 H OH O | | | O—C—O—C—CH 3 | | H CH 3 CO 2 H OH O | | | O—C—O—C—CH 3 | | H 3 C H CO 2 H OH O | | | O—C—O—C—CH 3 | | H 3 C H CO 2 H OH | | O—C—CH 3 + H 2 PO 4 CO 2 H O
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24Aspirin - Reminder: These notes are meant to supplement,...

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