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