OH Ac2O (1.0 equiv) -N 5 mol% Et3N (1.1 equiv) a. Provide a reasonable mechanism for this reaction that accounts for the role of 4- DMAP b. Pyridine itself is not very effective as a catalyst. Explain why.

OH Ac2O (1.0 equiv) -N 5 mol% Et3N (1.1 equiv) a. Provide a reasonable mechanism for this reaction that accounts for the role of 4- DMAP b. Pyridine itself is not very effective as a catalyst. Explain why.

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

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.63P

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Question

4-dimethylaminopyridine (4-DMAP) is a good catalyst for acylation of 2° alcohols

OH
Ac2O (1.0 equiv)
-N 5 mol%
Et3N (1.1 equiv)
a. Provide a reasonable mechanism for this reaction that accounts for the role of 4-
DMAP
b. Pyridine itself is not very effective as a catalyst. Explain why.

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