What evidences are used to prove that Benzene's kekule model is incorrect and that Benzene has a delocalised Pi structure.

The enthalpy Change of Hydration for cyclohexene is 120 kJmol-1 therefore if the Kekule model is correct then the Enthalpy change of Hydration would be 360 kJmol-1 however as it is considerably less than that the Kekule model cannot be accepted.Cyclohexene can act as a nucleophile and donate electrons to Bromine and turn Bromine water clear by reacting with the Bromine. However Benzene cannot, therefore suggesting that Benzene does not contain 3 seperate double bonds as it is not polar enough to donate electrons and polarise the Bromine molecule. Therefore the delocalised ring system is favoured.The Bond length in Benzene is unifrom as a hybrid between that of a carbon=carbon double bond and that of a carbon-carbon single bond therefore the Kekule model cannot be correct as it suggests two different bond lengths. However as the delocalised ring system suggests 6 bonds of hybrid length this is the favoured structure.

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Answered by Muin A. Chemistry tutor

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