Acid-catalyzed transesterification and Fischer esterification take place by nearly identical mechanisms. Transesterificationcan also take place by a base-catalyzed mechanism, but all attempts at base-catalyzed Fischer esterification (using -OR″,for example) seem doomed to failure. Explain why Fischer esterification cannot be catalyzed by base.2

Acid-catalyzed transesterification and Fischer esterification take place by nearly identical mechanisms. Transesterificationcan also take place by a base-catalyzed mechanism, but all attempts at base-catalyzed Fischer esterification (using -OR″,for example) seem doomed to failure. Explain why Fischer esterification cannot be catalyzed by base.2

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

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.50P

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