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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Acid-catalyzed transesterification and Fischer esterification take place by nearly identical mechanisms. Transesterification
can 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
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