Q.
The total number among following ethers which cannot be prepared by Williamson's synthesis is: CH3OCH2CH3,C6H5OCH3,(C6H5)2O,(CH3)3COCH3,(C2H5)2O,(CH3)3C−O−C(CH3)3
In Williamson's synthesis,
i. 1∘ alkyl halide and 3∘ alkoxide give the best yield of corresponding ethers.
ii. In case of, 3∘ 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, (C6H5)2O and (CH3)3C−O−C(CH3)3 cannot be prepared by Williamson's synthesis.