Methods of Preparation of Ethers
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322960 In the Williamson synthesis of ethers given by the general equation \(\mathrm{R}-\mathrm{X}+\mathrm{R}^{1} \mathrm{ONa} \longrightarrow \mathrm{R}-\mathrm{O}-\mathrm{R}^{1}\). The yield from \(\mathrm{R}-\mathrm{X}\) follows the sequence

1 \(\mathrm{CH}_{3}>1^{0}>2^{0}>3^{0}\)
2 \(\mathrm{CH}_{3} < 1^{0} < 2^{0} < 3^{0}\)
3 \(\mathrm{CH}_{3} < 1^{0}>2^{0}>3^{0}\)
4 \(\mathrm{CH}_{3}>1^{0} < 2^{0} < 3^{0}\)