Ch11 - Chapter 11 Aromaticity Aromaticity Benzene(11.3 11.4...

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1 Chapter 11 – Aromaticity Aromaticity Benzene (11.3, 11.4, 11.6, 11.19) Antiaromaticity (11.18) Other annulenes & Polycyclic Aromatic Compounds (11.20) Aromatic Ions (11.21) Aromatic Heterocyclic Compounds (11.23)
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2 11.4 Benzene Stability (A special class of reactivity) Heat of Hydrogenations H taking it all to sigma bonds) + Br Br Br Br Electrophilic Addition Reaction? -118 kJ/mol -230 kJ/mol -356 kJ/mol -206 kJ/mol Unexplained stability + Br Br Br Br + Br Br A new class “Aromatics” H We may expect H to be around -300 kJ/mol”
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3 11.3 & 11.6 Benzene: A special distribution of M.O.’s Benzene-An interesting creature Resonance forms –any bond is 1 parts sigma ½ parts pi How do we explain the equivalent bond lengths? Resonance theory & M.O. bonding theory C H 2 CH 2 Same Type of M.O. Distribution? No.
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4 11.19 Benzene : Hückel’s Rule (Filling this special dist. of M.O.’s) Benzene Energy 4n+2 Rule is satisfied when: Cyclic Conjugated Molecules Always have: A single lowest energy M.O.
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