Reactions with carboxylic acids and acid anhydrides require concentrated sulfuric acid, while reactions with acid chlorides use a base like pyridine. Acetylation, as seen in the production of aspirin from salicylic acid, involves introducing an acetyl group (CH₃CO) into alcohols or phenols.
What conditions are required for the reactions of alcohols and phenols with carboxylic acids, acid chlorides, and acid anhydrides to form esters, and how is acetylation related to the production of aspirin?
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For reactions with carboxylic acids, acid chlorides, and acid anhydrides to form esters, alcohols and phenols require the presence of an acid catalyst, such as sulfuric acid (H2SO4). Acetylation, involving the reaction of acetic anhydride with phenols, is a common process in the production of aspirin. In aspirin synthesis, acetylation of salicylic acid with acetic anhydride, facilitated by a mild acid catalyst like sulfuric acid, forms acetylsalicylic acid (aspirin). This reaction introduces an acetyl group to the phenolic ring, reducing the irritant properties of salicylic acid and enhancing the drug’s tolerability.