Chemistry / Unit 12 Chem 2457 short lesson, about 20 seconds
Aromatic Delocalization Favors Substitution
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The idea
Benzene's delocalized pi ring gives it unusual stability, so aromatic hydrocarbons undergo substitution rather than addition, preserving the ring intact.
In practice
Chlorine substitutes for a benzene hydrogen, leaving the ring's delocalized bonding intact, rather than adding across alternating double bonds.
Where people slip
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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