Explain the observation that attempted Fischer esterification of 2.4,6-trimethylbenzoic acid with methanol and HCl is unsuccessful. No ester is obtained, and the acid is recovered unchanged. What alternative method of esterification might be successful?

Explain the observation that attempted Fischer esterification of 2.4,6-trimethylbenzoic acid with methanol and HCl is unsuccessful. No ester is obtained, and the acid is recovered unchanged. What alternative method of esterification might be successful?

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Section21.SE: Something Extra

Problem 55AP

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Question

Explain the observation that attempted Fischer esterification of 2.4,6-trimethylbenzoic
acid with methanol and HCl is unsuccessful. No ester is obtained, and the acid is
recovered unchanged. What alternative method of esterification might be successful?

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