William Esther

[utdent20]

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i was going thru the roadmaps in the destroyer and I was confused about the william esther synthesis reaction. a benzene ring with a methylbromide attached undergoes NaOC2H5/DMSO , why is the product different than NaOC2H5/C2H5OH.
In that same road map

 

[Orgodox]

Good question. When its primary it does SN2 (williamson ether) but when its secondary it does elimination