Chapter 139 of 2363 min read
Ethers: preparation and cleavage
Why this is asked: Williamson synthesis is an SN2 reaction, so the alkyl halide half must be primary or unhindered — pair a bulky 3° alkyl halide with an alkoxide instead and you get an eliminated alkene, not the ether, because the strongly basic alkoxide just deprotonates it. In cleavage of an alkyl aryl ether by HI, the aryl–oxygen bond never breaks — the products are always phenol plus an alkyl iodide, never a haloarene.
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