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Author Question: Why does benzene undergo a substitution reaction with bromine, whereas cyclohexene undergoes an ... (Read 86 times)

ninaj

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on: Feb 17, 2022
Why does benzene undergo a substitution reaction with bromine, whereas cyclohexene undergoes an addition reaction with bromine?
◦ Cyclohexene has a mix of localized and delocalized π electrons, so substitution would disrupt this pattern and make the ring less stable.
◦ Benzene has delocalized π electrons not present in cyclohexene and adding bromine would result in a less stable, nonaromatic product.
◦ Benzene is highly unstable due to its lack of localized π electrons and this makes an addition reaction impossible.
◦ Benzene has localized π electrons and this forms a structure that is stable and very unreactive, preventing an addition reaction from occurring.
◦ Cyclohexene has delocalized π electrons that make it too stable to undergo an additional reaction.
Organic Chemistry ¦ Klein ¦ 4th Edition
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Marked as best answer by ninaj on Feb 17, 2022

KobyRhoads

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Reply #1 on: Feb 17, 2022
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ninaj

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Reply 2 on: Feb 17, 2022
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meow1234

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Reply 3 on: Yesterday
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