Whether the ortho-carboxy substituent acts as an intramolecular general-base catalyst or as an intramolecular nucleophilic catalyst can be determined by carrying out the hydrolysis of aspirin with 18O-labeled water and determining whether 18O is incorporated into ortho-carboxy-substituted phenol. Explain the results that would be obtained with the two types of catalysis.

Intramolecular base catalysis is catalysis where catalyst is a part of the molecule that undergoes…

Answered: Whether the ortho-carboxy substituent…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.63P

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Whether the ortho-carboxy substituent acts as an intramolecular general-base catalyst or as an intramolecular nucleophilic catalyst can be determined by carrying out the hydrolysis of aspirin with ¹⁸O-labeled water and determining whether ¹⁸O is incorporated into ortho-carboxy-substituted phenol. Explain the results that would be obtained with the two types of catalysis.

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