Write the reaction mechanism to prepare aspirin using concentrated sulfuric acidas a catalyst.
Question
Write the reaction mechanism to prepare aspirin using concentrated sulfuric acidas a catalyst.
Solution
The preparation of aspirin involves the reaction of salicylic acid with acetic anhydride, using concentrated sulfuric acid as a catalyst. Here is the step-by-step reaction mechanism:
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Protonation of the carbonyl group: The reaction begins with the protonation of the carbonyl group of acetic anhydride by the sulfuric acid. This makes the carbonyl carbon more electrophilic (electron-loving), and thus more susceptible to nucleophilic attack.
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Nucleophilic attack: The oxygen atom of the hydroxyl group in salicylic acid acts as a nucleophile and attacks the electrophilic carbonyl carbon in the protonated acetic anhydride. This forms a tetrahedral intermediate.
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Proton transfer: A proton from the newly formed hydroxyl group is transferred to one of the nearby oxygen atoms, resulting in the formation of a good leaving group.
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Leaving group departure: The good leaving group (a molecule of acetic acid) leaves, resulting in the formation of aspirin.
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Deprotonation: Finally, the aspirin molecule is deprotonated by a water molecule, returning the sulfuric acid catalyst to its original state and leaving the aspirin in its final, neutral form.
The overall reaction can be summarized as follows:
Salicylic acid + Acetic anhydride -> Aspirin + Acetic acid
This reaction is an example of acetylation, where an acetyl group is transferred from one molecule (in this case, acetic anhydride) to another (salicylic acid). The sulfuric acid acts as a catalyst, speeding up the reaction without being consumed in the process.
Similar Questions
Aspirin (acetylsalicylic acid) was synthesised in the following experiment:8.25 g of salicylic acid (Msalicylic acid = 138.13 g mol–1) was reacted with 10.0 g of ethanoic anhydride (Manhydride = 102.10 g mol–1) in the presence of a concentrated sulfuric acid catalyst. 8.55 g of a white solid was collected at the end of the reaction.salicylic acid + ethanoic anhydride → acetylsalicylic acid + ethanoic acidCalculate the percentage yield of aspirin. State your answer to three significant figures. Maspirin = 180.17 g mol–1.
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