Phenols (pKa ≈ 10) are more acidic than other alcohols, so they are easily deprotonated bysodium hydroxide or potassium hydroxide. The anions of phenols (phenoxide ions) can beused in the Williamson ether synthesis, especially with very reactive alkylating reagents suchas dimethyl sulfate. Using phenol, dimethyl sulfate, and other necessary reagents, show howyou would synthesize methyl phenyl ether.

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
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.36P: Claisen condensation between diethyl phthalate and ethyl acetate followed by saponification,...
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Phenols (pKa ≈ 10) are more acidic than other alcohols, so they are easily deprotonated by
sodium hydroxide or potassium hydroxide. The anions of phenols (phenoxide ions) can be
used in the Williamson ether synthesis, especially with very reactive alkylating reagents such
as dimethyl sulfate. Using phenol, dimethyl sulfate, and other necessary reagents, show how
you would synthesize methyl phenyl ether.

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