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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.
Delocalized model structure
p orbitals from each carbon overlap with two neighbouring p orbitals.
forms a pi cloud of delocalised electron
stable
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.
Halogenation (chlorination)
benzene + halogen carrier.
Cl2 + AlCl3 —> AlCl4- + Cl+
Nitration
benzene + conc HNO3 + conc H2SO4.
HNO3 + H2SO4 —> NO2 + HSO4- + H2O
Alkylation
benzene + halogen + (halogen carrier)
CH3 + AlCl3 —> AlCl4- + CH3+
Acylation
benzene + acyl chloride (using halogen carrier)
CH3COCl + AlCl3 —> AlCl4- + CH3CO+