Transcription of Chapter 15: Benzene and Aromaticity
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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 styreneGener
Polycyclic aromatic hydrocarbons Aromatic compounds can have rings that share a set of carbon atoms (fused rings) Compounds from fused benzene or aromatic heterocyclic rings are themselves aromatic Naphthalene: 4n+2=10, n=2 note: Hückels rule is strictly for monocyclic aromatic compound, its application to polycyclic aromatic compounds is tenuous.
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Toxicity of Polycyclic Aromatic Hydrocarbons PAHs, Polycyclic aromatic hydrocarbons, Aromatic, POLYCYCLIC AROMATIC, Of polycyclic, Risk assessment approaches for, Risk assessment approaches for polycyclic aromatic hydrocarbons, Carcinogens, PAHs, Alkenes, Alkynes and Aromatic Compounds, Aromatic hydrocarbons, Plastic