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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
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
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.50P
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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.
Transcribed Image Text: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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