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Ethers can be prepared by Williamson syn...

Ethers can be prepared by Williamson synthesis in which an alkyl halide is reacted with sodium alkoxide. Di-tert-buty ether can't be prepared by this method. Explain

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Williamson's synthesis occurs by `S_(N)2` mechanism in which sodium alkoxide reacts with an alkyl halide. Now to prepare di-tert-butyl ether, sodium tert-butoxide must be reacted with tert-butyl bromide. Since `3^(@)` alkyl halides prefer to undergo elimination rather than substitution, therefore, sodium tert-butoxide reacts with tert-butyl bromide and favours elimination to form isobutylene rather than substitution to form di-tert-butyl ether.

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