Whether the ortho-carboxy substituent acts as an intramolecular general-base catalyst or

Chapter 22, Problem 13

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

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