17.2 Aromatic vs Nonaromatic vs Antiaromatic

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    CRITERIA FOR AROMATIC COMPOUNDS
    1 Cyclic and conjugated
    2 Each atom in the ring must have an unhybridized p orbital
    (No sp3-hybridized atoms in the ring)
    3 Planar
    4 Delocalization of the pi electrons must lower the electronic energy
    -4N+2 π electrons (odd # of pairs)
    Antiaromatic compounds satisfy the first 3 rules above but have 4N π electrons.
    Nonaromatic compounds don't satisfy one or more of the first 3 rules above.
    benzene kekule structures
    benzene p orbitals aromatic

    Classify the following as aromatic, nonaromatic, or antiaromatic.

    (All of these examples are classified in the video lesson.)

    1,3,5-hexatriene nonaromatic
    cyclopentadiene nonaromatic
    cyclobutadiene antiaromatic
    benzene aromatic
    pyridine aromatic
    pyrrole aromatic
    azirine nonaromatic
    furan aromatic
    classify 09
    cyclooctatetraene nonaromatic
    cyclopentadienyl cation aromatic
    tropylium cation aromatic
    [14]annulene aromatic