Synthesis of Aspirin from Salicylic Acid & Acetic Anhydride

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SUMMARY

The discussion focuses on the acid-catalyzed synthesis of aspirin from salicylic acid and acetic anhydride. The mechanism involves a substitution reaction where the hydroxyl (OH) group of salicylic acid is replaced by the acetyl group from acetic anhydride. The initial step includes the protonation of the hydroxyl group, facilitating the departure of water and allowing the acetyl group to attack the oxygen atom. This reaction is analogous to Fischer esterification, highlighting the importance of understanding acid-catalyzed mechanisms in organic chemistry.

PREREQUISITES
  • Understanding of organic chemistry reaction mechanisms
  • Familiarity with acid-catalyzed reactions
  • Knowledge of functional groups, specifically hydroxyl and carbonyl groups
  • Experience with substitution reactions
NEXT STEPS
  • Study the detailed mechanism of Fischer esterification
  • Learn about acid-catalyzed reactions in organic synthesis
  • Explore the role of catalysts in substitution reactions
  • Investigate the properties and reactivity of acetic anhydride
USEFUL FOR

Chemistry students, organic chemists, and educators looking to deepen their understanding of reaction mechanisms and the synthesis of acetylated compounds.

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Homework Statement


Write the complete mechanism for the acid-catalyzed formation of aspirin from salicylic acid and acetic anhydride


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The Attempt at a Solution


I basically know the reaction but I'm not sure how to start the mechanism...Like i know that it is a substitution reaction where the OH group and the CH3--C==O switch places but how does it start? Does the the H group from the OH group first leave, then the CH3--C==O group can attack the O?
 
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Its a bit like Fisher Esterification.
 

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