Chap15 - Aromaticity. Reactions of Benzene Reactions...

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Chapter 15 1 Aromaticity. Aromaticity. Reactions of Benzene Reactions of Benzene Chapter 15 Chapter 15
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Chapter 15 2 Contents of Chapter 15 Aromaticity Heterocyclic Compounds Chemical Consequences of Aromaticity Molecular Orbital Description of Aromaticity Reactivity Considerations Mechanism for Electrophilic Substitution Halogenation/Nitration/Sulfonation of Benzene Friedel–Crafts Reactions
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Chapter 15 3 Aromaticity Benzene is a cyclic compound which has a planar structure with a delocalized cloud of π electrons above and below the plane of the ring
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Chapter 15 4 Criteria for Aromaticity There must be an uninterrupted ring of p orbital- bearing atoms leading to a delocalized π cloud For the π cloud to be cyclic, the molecule must be cyclic For the π cloud to be uninterrupted, every ring atom must have a p orbital For the π cloud to form, each p orbital must be able to overlap the p orbital on either side
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Chapter 15 5 Criteria for Aromaticity The π cloud must have an odd number of pairs of π electrons, or (2n+1) 2 = 4n+2 π electrons Hückel’s rule
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Chapter 15 6 Aromaticity cyclooctatetraene is non aromatic It is not planar
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Chapter 15 7 Aromaticity resonance broken 2 π electrons 4 π electrons nonaromatic aromatic antiaromatic
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Chapter 15 8 Aromaticity
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9 Aromaticity The criteria for aromaticity also can be applied to polycyclic hydrocarbons Naphthalene (5 pairs of
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Chap15 - Aromaticity. Reactions of Benzene Reactions...

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