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CH 14-2 Characteristics of Benzene
Hydrogen deficiency All carbons in ring are sp2 hybridized Geometry Reactivity of benzene vs alkenes Benzene is ONE example of a class of compounds characterized as “AROMATIC.” These compounds possess the physical property of “AROMATICITY.” AROMATICITY is a physical property that explains the unique stability, reactions and toxicity of benzene and related compounds.
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Aromaticity Conjugation: each atom of the ring has a p-orbital.
Delocalization: since the p-orbitals are all conjugated, the pi electrons can move freely from one orbital to the next; the pi electrons are delocalized.
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Resonance: conjugated, delocalized pi electrons lead to resonance structures:
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Historical Representations of Benzene
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How can we tell if a compound is aromatic?
Huckel’s Rule: Aromaticity exists if # pi electrons = 4n + 2 Since n = any whole #, there are Huckle #’s of pi electrons for aromatic compounds (n = 0, 1, 2, 3: 2, 6, 10, 14, etc. Lone electron pair can count towards aromaticity Why are these compounds non-aromatic?
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Aromatic Ions
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