The following ether that cannot be prepared by a Williamson ether synthesis is Tert-butyl phenyl ether. Option D.
In Williamson ether synthesis alkoxides react with primary alkyl halides or sulfonate esters. Alkoxides are made from the conjugate bases of alcohols and consist of an R group attached to an oxygen atom. They are often written RO-, where R is an organic substituent.
Williamson synthesis always uses primary alkyl halides. Williamson's synthesis requires tert-butyl bromide and sodium tert-butoxide to produce di-tert-butyl ether. The product obtained is isobutylene and not di-tert-butyl ether. It is used in the production of both simple and mixed ethers. Alkyl halides are heated with alcoholic sodium or potassium alkoxides to form the corresponding ethers.
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