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Question: Answered & Verified by Expert
In Williamson synthesis if tertiary alkyl halide is used than
ChemistryAlcohols Phenols and EthersVITEEEVITEEE 2018
Options:
  • A ether is obtained in good yield
  • B ether is obtained in poor yield
  • C alkene is the only reaction product
  • D a mixture of alkene as a major product and ether as a minor product forms.
Solution:
2624 Upvotes Verified Answer
The correct answer is: alkene is the only reaction product
If a tertiary alkyl halide is used, an alkene is the only reaction product and no ether is formed. For example, the reaction of $\mathrm{CH}_{3} \mathrm{ONa}$ with $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{Br}$ gives exclusively 2-methylpropene.



It is because alkoxides are not only nucleophiles but strong bases as well. They react with alkyl halides leading to elimination reactions.

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