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Chap07 - Electron Delocalization and Resonance Chapter 7...

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Chapter 7 1 Electron Delocalization and Electron Delocalization and Resonance Resonance Chapter 7 Chapter 7
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Chapter 7 2 Contents of Chapter 7 Benzene Delocalized Electrons and Resonance Stability of Allylic and Benzylic Cations and Radicals Effect of Electron Delocalization on p K a Molecular Orbital Description of Stability Relative Stabilities of Dienes Reactivity Considerations Electrophilic Addition Reactions Direct (1,2-) and Conjugate (1,4-) Additions Thermodynamic vs. Kinetic Control Diels-Alder Reaction
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Chapter 7 3 Delocalized Electrons and Resonance
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Chapter 7 4 Bonding in Benzene (a) Carbon–carbon and carbon–hydrogen σ bonds (b) Carbon p-orbitals overlap with neighbors (c) Cloud of π electrons above and below ring (d) Electrostatic potential map for benzene
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Chapter 7 5 Delocalized Pi Systems Extend continuously through all connected atoms which lack 4 single bonds (except H) Broken up by saturated atoms with 4 single bonds (C). Two double bonds on same carbon break up system (cumulated dienes) Broken by two saturated connected atoms with same Lewis acid/base properties (ie. 2 O atoms or C+ connected to B) O B N C O H H H H Two separa te p i systems broken up by sa tura ted te trava len t carbon + : : .. .. ..
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Chapter 7 6 Resonance Tricks Lone-Pair/Double-Bond Interconversion One atom charge goes down, other goes up. Atom receiving e’s has charge go more negative. O H - + + + : .. .. .. .. .. .. : O H O O
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Chapter 7 7 Resonance Tricks Double Bond Flip Double bond flips like page in book Instability (+, -, or •) jumps 1,3 Electrons move diff. but effect same for +-• - + + . . - .. ..
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Chapter 7 8 Resonance Tricks Electron Dominoes Combinations of interconversions and flips Instability moves thru pi system in 2-atom increments.
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