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: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
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Chapter13: Substitution
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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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