Which of the following cannot be made by using Williamson's synthesis?
Which of the following cannot be made by using Williamson's synthesis?
Methoxybenzene
Benzyl $p$ -nitrophenyl ether
Methyl tertiary butyl ether
Di-tert-butyl ether
Solution
The two components should be $\left(\mathrm{CH}_{3}ight)_{3} \mathrm{CONa}$ $\left(\mathrm{CH}_{3}ight)_{3} \mathrm{CBr}$. However, tert-alkyl halides tend to undergo elimination reaction rather than substitution leading to the formation of an alkene, $\mathrm{Me}_{2} \mathrm{C}=\mathrm{CH}_{2}$