Transcription of Chapter 15: Benzene and Aromaticity
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Chapter 15: Benzene and Aromaticity
11 Chapter 15: Benzene and AromaticityHHHHHHHHHHHHC6H62 - bonding MO -antibonding MOMO s of a C=C -bond * +235 KJ/mol-235 KJ/molfrom Chapter 123 -molecular orbitals of butadiene0 Nodes 3 bonding interactions 0 antibonding interactionsBONDING MO1 Nodes 2 bonding interactions 1 antibonding interactions bonding MO2 Nodes 1 bonding interactions 2 antibonding interactions ANTIBONDING MO3 Nodes 0 bonding interactions 3 antibonding interactions ANTIBONDING MO 2 is the Highest Occupied Molecular Orbital (HOMO) 3 is the Lowest Unoccupied Molecular Orbital (LUMO)4 1 of Butadiene (no nodes, bonding MO)The four -electrons in 1 are delocalizedover the four p-orbitals _+ _+ H3 CCH3H2 CCH2H2 CCHCH3H2 CCHCHCH2H2 CCHCHCH2 Table (p. 528): Bond lengths in pm154 133 149 148 134 bonding Interaction35!1!2!3!4!5!6 -molecular orbitals of hexatrienefive nodesfour nodesthree nodestwo nodesone nodezero nodes6 AO s = 6 MO ssix p-orbitals6 Conjugation: series of overlapping p-orbitalsAromaticity: cyclic conjugated organic compounds such as Benzene , that exhibit special stability due to resonancedelocalization of : Naming aromatic compounds: (arenes)large number on non-systematic names (Table )CH3 OHOCH3NH2benzene toluene phenol anisole anilin e styreneGenerally, mono-substit
1 1 Chapter 15: Benzene and Aromaticity H H H H H H H H H H H H C 6H 6 2 π-bonding MO π-antibonding MO MO’s of a C=C π-bond π* π +235 KJ/mol-235 KJ/mol from Chapter 1
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