(Solved): 2. Formation of Ethers Part 2. Formation of Ethers The Williamson ether synthesis is an organic reac ...

Part 2. Formation of Ethers The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol another $\mathrm{Sn}2$ reaction. To use an alkoxide as a nucleophile, an alcohol must first be deprotonated. - Draw the acid-base reaction needed to prepare an alkoxide ion. ${\mathrm{CH}}_3\mathrm{OH}$ B: $\mathrm{NaOH}$ is not a strong enough base to fully deprotonate an alcohol. Alcohols typically have a pKa of 16-17; the ${\mathrm{pK}}_4$ of ${\mathrm{H}}_2\mathrm{O}$ is also about 16 . A stronger base is needed such as $\mathrm{RO};\mathrm{H};{\mathrm{R}}_2\mathrm{N}$. - Write a general mechanism for the formation of an ether from an alkyl halide with an alkoxide as the nucleophile. Practice Problems - Predict the product for each of the following ether formation reactions. Note: The order of deprotonation vs nucleophilic substitution is important. $\begin{array}{l}\text{ Strong }\\ \text{ Base }\end{array}$