The Williamson ether synthesis involves treatment of a haloalkane with a metal alkoxide. Following are two reactions intended to give benzyl tert-butyl ether. One reaction gives the ether in good yield, and the other reaction does not. Which reaction gives the ether? What is the product of the other reaction, and how do you account for its formation? CH3 CH3 (a) CH,CO K* + 1. ČH3 -CH,CI CH,COCH,- + KCI DMSO ČH3 CH3 CH3 (b) -CH,O K* + CH,CI CH,COCH,- + KCI DMSO ČH3 CH3

The Williamson ether synthesis involves treatment of a haloalkane with a metal alkoxide. Following are two reactions intended to give benzyl tert-butyl ether. One reaction gives the ether in good yield, and the other reaction does not. Which reaction gives the ether? What is the product of the other reaction, and how do you account for its formation? CH3 CH3 (a) CH,CO K* + 1. ČH3 -CH,CI CH,COCH,- + KCI DMSO ČH3 CH3 CH3 (b) -CH,O K* + CH,CI CH,COCH,- + KCI DMSO ČH3 CH3

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

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.48P: The Williamson ether synthesis involves treatment of a haloalkane with a metal alkoxide. Following...

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