Part of JOC-05 — Alcohols, Phenols & Ethers

Reactions of Anisole — Electrophilic Substitution

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Anisole (methoxybenzene, C6H5OCH3) has -OCH3 group which is +M (activating, o/p director). The +M effect outweighs the weak -I effect. Bromination: C6H5OCH3 + Br2/CH2Cl2 -> mixture of o-bromoanisole and p-bromoanisole (para major). Friedel-Crafts acylation: Works on anisole (unlike phenol) because -OCH3 doesn't coordinate strongly to AlCl3. CH3COCl/AlCl3 -> p-methoxyacetophenone (major). Friedel-Crafts alkylation: Also works. CH3Cl/AlCl3 -> o- and p-methyl anisole. Anisole is useful in JEE as a contrast to phenol — same activating effect but FC reactions work because the lone pair on O is partially tied up by the methyl group.

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