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Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers

Which of the following ethers cannot be prepared by Williamson ether synthesis?

Options

  1. ACH ₂= CH - CH ₂- O - CH ₃
  2. BCH ₃- CH = CH - O - CH = CH ₂
  3. CPhOCH ₃
  4. D( CH ₃ )₃ C - O - CH ₂ CH ₂ CH ₃

Correct answer

B. CH ₃- CH = CH - O - CH = CH ₂

Step-by-step solution

Williamson ether synthesis involves an S_ N 2 reaction between an alkoxide or aroxide ion and an alkyl halide. For the S_ N 2 reaction to proceed successfully, the alkyl halide must have the halogen attached to an sp³ hybridized carbon (preferably primary or methyl). In option (A), CH ₂= CH - CH ₂- O - CH ₃ can be prepared by reacting sodium methoxide with allyl halide, or sodium allyloxide with methyl halide. In option (B), CH ₃- CH = CH - O - CH = CH ₂ has oxygen bonded to two sp² hybridized vinylic carbons. Its

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