Question
Which of the following can easily undergo Williamson's synthesis to prepare ether?
Solution
Ethers containing substituted alkyl groups such as secondary and tertiary may also prepared by this method. But better results are obtained in primary alkyl halide. Thus, CH3CH2CH2Br undergoes Williamson’s synthesis because it is 1° alkyl halide, 
-carbon is less hindered while in (CH3)3CCH2Br (although it is 1°), 
-carbon is highly crowded and difficult for alkoxide ion to attack.
-carbon is less hindered while in (CH3)3CCH2Br (although it is 1°), -carbon is highly crowded and difficult for alkoxide ion to attack.
