To prepare ethyl tert-butyl ether via the Williamson ether synthesis in the highest yield, which com — Alcohols Phenols and Ethers Chemistry Question

💡 Solution & Explanation

The Williamson synthesis proceeds via an $S_N2$ mechanism. To avoid steric hindrance and $E2$ elimination, the alkyl halide must be primary (unhindered). Therefore, unhindered ethyl bromide must be reacted with the bulky sodium tert-butoxide. Using tert-butyl bromide would exclusively yield isobutylene.