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

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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
Transcribed Image Text: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
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