1. Tardigrade
  2. Question
  3. Chemistry
  4. How many of the following ethers CANNOT be prepared by Williamson's synthesis? CH 3 OCH 2 CH 3, C 6 H 5 OCH 3,( C 6 H 5)2 O , ( CH 3)3 COCH 3,( C 2 H 5)2 O ,( CH 3)3 C - O - C ( CH 3)3

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Q. How many of the following ethers CANNOT be prepared by Williamson's synthesis?
$CH _{3} OCH _{2} CH _{3}, C _{6} H _{5} OCH _{3},\left( C _{6} H _{5}\right)_{2} O , \left( CH _{3}\right)_{3} COCH _{3},\left( C _{2} H _{5}\right)_{2} O ,\left( CH _{3}\right)_{3} C - O - C \left( CH _{3}\right)_{3}$

Alcohols Phenols and Ethers

Solution:

In Williamson's synthesis,
i. $1^{\circ}$ alkyl halide and $3^{\circ}$ alkoxide give best yield of corresponding ethers.
ii. In case of, $3^{\circ}$ alkyl halide, elimination competes over substitution and alkene is obtained as a product.
iii. Aryl halides do not undergo nucleophilic substitution unless it is activated by the presence of electron withdrawing group.
Thus, $\left( C _{6} H _{5}\right)_{2} O$ and $\left( CH _{3}\right)_{3} C - O - C \left( CH _{3}\right)_{3}$ cannot be prepared by Williamson's synthesis.