Why does the phenolic -OH react with acetic anhydride but not acidic -OH in Aspirin synthesis from salicylic acid and acetic anhydride?

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Adel Amer

Yes, the phenolic oxygen is !

Akhil Sivan

Yes. Because, the product determining step involves the attack of the phenolic -OH to the protonated anhydride and is directed by the greater nucleophilicity of phenolic -OH rather than carboxylic -OH.

Hirbod Karimi

Madhukar Baburao Deshmukh

Phenolic OH is more reactivetowards acetic anhydride than acidic OH because Charge density is distributed among two Oxygens of carboxylic group (Lower nucleophilicity).