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The cation formed upon addition of an electrophile to benzene is highly stabilized by resonance,whereas the cation formed to an alkene is stabilized by hyperconjugation. The loss of a proton in benzene is favourable due to the restoration of the cyclic pi-system.

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13y ago
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14y ago

Because benzene does not have localized pi bond but has an electronic cloud which is responsible its aromatic character and stability, to retain its stability benzene undergoes substitution reactions rather than addition.

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11y ago

Resonance structure of benzene shows that carbon-carbon bond in benzene is neither double bonded nor single bonded, but half way between them. So benzene undergoes substitution reactions.

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Q: Why benzene undergoes electrophilic substitution reaction whereas alkenes undergoes addition reaction?
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