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(i) State two anomalies that made research scholars to reject the Kekule structure for benzene. (ii) Using appropriate structures briefly describe Linus Pauling’s resonance structure of benzene. (iii) Show how Pauling’s resonance theory explained the anomalies observed in Kekule’s structure. (iv) Give two reasons, in addition to Pauling’s resonance theory, for stability of benzene. (v) Compare the stabilities of cyclohexene, 1, 3-cyclohexadiene, and benzene based on heat of hydrogenation. (vi) Give the conditions for aromatic, anti-aromatic and non-aromatic compound. (vii) The enthalpy of hydrogenation of benzene is –208kJ mol–1. Explain why this value differs from that you have obtained for cyclohexa-1,3,5-triene. (viii) Estimate a value for the enthalpy of hydrogenation of the hypothetical molecule cyclohexa 1,3,5-triene, given that the enthalpy of hydrogenation of cyclohexene is –119.6 kJ mol–1.
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