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Ethers can be prepared by Williamson synthesis in which an alkyl halidde is reacted with sodium alkoxide. Di-tert-butyl ether can't be prepared by this method. Explain. |
Answer» Solution :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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