CHEM 222 Chapter Notes - Chapter 13: Molecular Orbital Theory, Antibonding Molecular Orbital, Unpaired Electron

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13. 1 introduction: conjugated system: at least one atom with p orbital adjacent to at least one pi bond, allylic: radial, cation or anion that is adjacent to 1+ pi bonds in molecule other than propene. 13. 2 stability of allyl radical: stability can be explained in terms of molecular orbital theory or resonance. Molecular orbital description: as allylic h atom abstracted from propene, carbon"s hybridization changes from sp3 to sp2, p orbital of new sp2 hybridized c atom overlaps with p orbitals of central c atom. In allyl radical, three p orbitals overlap to form set of pi mos that encompass all. 13. 3 allyl cation: carbocations can be allylic, allyl cation is more stable than secondary carbocation, almost as stable as tertiary. 13. 4 resonance theory revisited: energy of actual resonance molecule is lower than the energy of the contributing structures, more stable structure = greater contribution to hybrid.

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