11%20Ch07 - CHAPTER 7 Delocalized Electrons and Their...

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201 CHAPTER 7 Delocalized Electrons and Their Effect on Stability, Reactivity, and p K a More About Molecular Orbital Theory Important Terms 1,2-addition addition to the 1- and 2-positions of a conjugated system. (direct addition) 1,4-addition addition to the 1- and 4-positions of a conjugated system. (conjugate addition) allene a compound with two adjacent double bonds. allylic carbon a carbon adjacent to an sp 2 carbon of a carbon-carbon double bond. allylic cation a compound with a positive charge on an allylic carbon. antibonding molecular the molecular orbital formed when out-of-phase orbitals overlap. antiymmetric molecular a molecular orbital that does not have a plane of symmetry but would have if one orbital half of the MO were turned upside down. aromatic compound compounds that are unusually stable because of large delocalization energies (see Section 14.1). benzylic carbon a carbon, joined to other atoms by single bonds, that is bonded to a benzene ring. benzylic cation a compound with a positive charge on a benzylic carbon. bonding molecular orbital the molecular orbital formed when in-phase orbitals overlap. bridged bicyclic compound a bicyclic compound in which the rings share two nonadjacent carbons. common intermediate an intermediate that two compounds have in common. concerted reaction a reaction in which all the bond making and breaking processes occur in a single step. conjugate addition addition to the 1- and 4-positions of a conjugated system. conjugated diene a compound with two conjugated double bonds. conjugated double bonds double bonds separated by one single bond. contributing resonance a structure with localized electrons that approximates the true structure of a structure compound with delocalized electrons. cumulated double bonds double bonds that are adjacent to one another. cycloaddition reaction a reaction in which two π -electron-containing reactants combine to form a cyclic product.
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202 Chapter 7 [4 + 2] cycloaddition a cycloaddition reaction in which four π electrons come from one reactant and reaction two electrons come from the other reactant. delocalization energy the extra stability associated with a compound as a result of having (resonance energy) delocalized electrons. delocalized electrons electrons that are not localized on a single atom or between two atoms. Diels-Alder reaction a [4 + 2] cycloaddition reaction. diene a hydrocarbon with two double bonds. dienophile an alkene that reacts with a diene in a Diels-Alder reaction. direct addition addition to the 1- and 2-positions of a conjugated system. (1,2-addition) donation of electrons by donation of electrons through bonds. resonance electron delocalization the sharing of electrons by more than two atoms. endo a substituent is endo if it and the bridge are on opposite sides of the bicyclic compound.
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This note was uploaded on 03/29/2010 for the course CHE 118A 118a taught by Professor Kent during the Spring '10 term at UC Davis.

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11%20Ch07 - CHAPTER 7 Delocalized Electrons and Their...

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