ch16 - antiaromatic (N is an integer 0, 1, 2, etc.)...

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Chapter 16 – page 1 Chapter 16 – Aromatic Compounds CHM 2211 – Davidson 1. Benzene Most organic compounds can be classified as aliphatic or aromatic o Aliphatic – “fat-like” o Aromatic – originally due to pleasant odor, but now because of stability Kekulé’s Structure of Benzene The Resonance Representation Reactivity
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Chapter 16 – page 2 2. Aromatic, Antiaromatic, and Nonaromatic Compounds To be aromatic , must fit the following criteria: o Cyclic with a conjugated pi system o Unhybridized p orbital on each atom o Structure must be planar o Delocalization of pi electrons must decrease energy of system Antiaromatic – actually higher in energy Non-aromatic – missing one of the first three criteria Examples Hückel’s Rule – shortcut to determining aromaticity – be sure to check first three criteria! o Count the number of pi electrons o If the total is (4N + 2), then it is aromatic o If the total if (4N), then it is
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Unformatted text preview: antiaromatic (N is an integer 0, 1, 2, etc.) Examples Chapter 16 page 3 3. Aromatic Ions Cyclopentadienyl Ions Cycloheptatrienyl Ions Cyclooctatetraene Dianion Other Examples can explain polarity Chapter 16 page 4 4. Heterocyclic Aromatic Compounds Pyridine and Pyrrole Other Nitrogen-Containing Aromatics Furan and Thiophene 5. Polynuclear Aromatic Hydrocarbons Fused rings share two carbon atoms and the bond between them Chapter 16 page 5 Examples Stability 6. Other Aromatic Hydrocarbons Allotropes of Carbon Diamond and Graphite (Fig. 16-15) Fullerenes C 60 and others Nanotubes 7. Nomenclature of Benzene Derivatives Several common names to know page 732 Chapter 16 page 6 Naming disubstituted benzenes ortho, meta, and para Note: can only use with disubstituted!...
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This note was uploaded on 06/18/2008 for the course CHM 2211 taught by Professor Castalleano during the Spring '06 term at University of Florida.

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ch16 - antiaromatic (N is an integer 0, 1, 2, etc.)...

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