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Chemistry  /  Chem 2457  ·  Atom · ~20 seconds

Aromatic Delocalization Favors Substitution

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Benzene's delocalized pi ring gives it unusual stability, so aromatic hydrocarbons undergo substitution rather than addition, preserving the ring intact.

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Chlorine substitutes for a benzene hydrogen, leaving the ring's delocalized bonding intact, rather than adding across alternating double bonds.

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Drawing benzene with alternating bonds invites treating it like an alkene — its real delocalized structure resists the addition chemistry that drawing predicts.

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