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COMEDK · Chemistry · 26. Alcohols Phenols and Ethers

Which of the following compound cannot be prepared by Williamson's synthesis?

  1. A \(\left(\mathrm{C}_2 \mathrm{H}_5\right)_2 \mathrm{O}\)
  2. B \(\left(\mathrm{CH}_3\right)_3 \mathrm{COC}\left(\mathrm{CH}_3\right)_3\)
  3. C \(\left(\mathrm{CH}_3\right)_3 \mathrm{COCH}_2 \mathrm{CH}_3\)
  4. D \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{OCH}_2 \mathrm{CH}_3\)
Verified Solution

Answer & Solution

Correct Answer

(B) \(\left(\mathrm{CH}_3\right)_3 \mathrm{COC}\left(\mathrm{CH}_3\right)_3\)

Step-by-step Solution

Detailed explanation

Williamson synthesis involves the reaction of an alkoxide ion with an alkyl halide via an \(S_{N}2\) mechanism. Since \(S_{N}2\) reactions are highly sensitive to steric hindrance, the alkyl halide used must be primary for the reaction to proceed efficiently. If a tertiary alkyl…