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The Williamson ether synthesis involves:
AReaction of an alcohol with concentrated H₂SO₄
BReaction of an alkene with water
CReaction of an alcohol with another alcohol over Al₂O₃
DReaction of an alkyl halide with a sodium alkoxide (Na+OR⁻) — SN2 mechanism; best with primary alkyl halide + bulky alkoxide
Answer & Solution
Correct answer: D. Reaction of an alkyl halide with a sodium alkoxide (Na+OR⁻) — SN2 mechanism; best with primary alkyl halide + bulky alkoxide
**Williamson synthesis**: R-X + R'O⁻Na⁺ → R-O-R' + NaX (SN2). Best when **R-X is primary** (3° alkyl halides give E2 elimination → alkene; not ether). For unsymmetric ethers, use the bulky alkoxide with the less hindered alkyl halide. E.g., **PhO⁻Na⁺ + CH₃I → PhOCH₃** (anisole).
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