The chemical reactivity of ethers with halogens is heavily dependent on the reaction conditions. Whi — Alcohols Phenols and Ethers Chemistry Question

💡 Solution & Explanation

In the dark, moderate chlorination occurs specifically at the $\alpha$ -carbons (adjacent to the oxygen) due to the resonance stabilization of the intermediate radical by oxygen's lone pairs (forming $\alpha,\alpha'$ -dichlorodiethyl ether). Under bright sunlight with excess $Cl_2$, a massive free-radical chain reaction replaces every single hydrogen atom, yielding perchlorodiethyl ether.