Benzene

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7 Terms

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Why is Kekules model incorrect?

  • benzene doesn’t undergo electrophilic addition.

  • all bonds are the same length.

  • enthalpy change of hydrogenation was less exothermic than expected.

2
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Delocalized model structure

  • p orbitals from each carbon overlap with two neighbouring p orbitals.

  • forms a pi cloud of delocalised electron

  • stable

3
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why cant benzene polarise Bromine?

  • not dense enough, lower electron density of pi system in benzene compared to electron density of pi bonds in alkene.

  • electron density spread all over rather than focused on one carbon.

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Halogenation (chlorination)

  • benzene + halogen carrier.

  • Cl2 + AlCl3 —> AlCl4- + Cl+

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Nitration

  • benzene + conc HNO3 + conc H2SO4.

  • HNO3 + H2SO4 —> NO2 + HSO4- + H2O

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Alkylation

  • benzene + halogen + (halogen carrier)

  • CH3 + AlCl3 —> AlCl4- + CH3+

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Acylation

  • benzene + acyl chloride (using halogen carrier)

  • CH3COCl + AlCl3 —> AlCl4- + CH3CO+