Sulfonation of alcohols to form mesylates, tosylates, or triflates turns the ordinarily poor alcohol-leaving group into a good resonance- stabilized leaving group. Consider the synthetic scheme below, which involves a sulfonation, and predict the product of the two-step sequence. :.... : OH 1. MsCl 2. (CH3)3CONa

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 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...
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Sulfonation of alcohols to form mesylates, tosylates, or triflates turns the ordinarily poor alcohol-leaving group into a good resonance-
stabilized leaving group. Consider the synthetic scheme below, which involves a sulfonation, and predict the product of the two-step
sequence.
: OH
744
1. MsCl
2. (CH3)3CONa
Transcribed Image Text:Sulfonation of alcohols to form mesylates, tosylates, or triflates turns the ordinarily poor alcohol-leaving group into a good resonance- stabilized leaving group. Consider the synthetic scheme below, which involves a sulfonation, and predict the product of the two-step sequence. : OH 744 1. MsCl 2. (CH3)3CONa
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