Ch 14

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mckenzielarmstrong
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192407
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Ch 14
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2013-01-12 14:27:02
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Aromatic Compounds
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Ch 14
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  1. An aromatic six-carbon ring with the molecular formula C6H6 ; each carbon atom is sp2 hybridized with one p orbital that contains one electron. Also called [6]annulene.
    Benzen
  2. A nonaromatic compound such as an alkane, cycloalkane, alkene, alkyne, or one of their derivatives
    Alipathic compound
  3. A planar cyclic conjugated system that is stabilized by electron delocalization
    Aromatic compound
  4.  The C6H5- group; obtained by removing a hydrogen atom from benzene, C6H6 . Abbreviated Ph- or φ- .
    Phenyl group
  5. The C6H5CH2- group; obtained by removing a hydrogen atom from the methyl group of toluene, C6H5CH3 . Abbreviated Bn-
    Benzyl group
  6. Having a 1,2 relationship on a benzene ring.
    Ortho
  7. Having a 1,3 relationship on a benzene ring.
    Meta
  8. Having a 1,4 relationship on a benzene ring.
    para
  9. Replacement of a hydrogen on a benzene ring by a strong electrophile.
    Benzene substitution
  10. The extra stability of a molecule that has resonance contributors, since the energy of the actual molecule is lower than the energy that is estimated for any of its resonance structures.
    Resonance stabiliztion
  11. The energy of stabilization that represents the difference in energy between the actual molecule or ion and that calculated for any resonance structure; this lower energy state arises from delocalization of electrons, and it results in resonance stabilization.
    Resonance energy
  12. The number of chemical bonds between a pair of atoms, which is an index of bond strength. In molecular orbital theory, bond order is defined as the difference between the number of bonding electrons and the number of antibonding electrons, divided by two. For example, the bond order for a carbon-carbon bond is 1 for ethane, 2 for ethene, 3 for ethyne, and 1.5 for benzene.
    Bond order
  13. Computer generated structure that uses color to show the relative distribution of electron density at the Van der Waals surface of a molecule or ion; violet and blue show electron-poor regions that have a partial positive charge (δ+); green and yellow show regions of normal electron density with almost no charge; orange and red show electron-rich regions that have a partial negative charge (δ─). Also called map of electrostatic potential.
    Electrostatic potential map
  14. A rule stating that planar monocyclic rings with (4n + 2) delocalized pi electrons will be aromatic; Hückel numbers include 2, 6, 10, 14, 18, 22, 26, 30, . . .
    Huckel's rule
  15. Monocyclic hydrocarbon characterized by a completely conjugated system of double bonds, which may or may not be aromatic. The ring size of an annulene is represented by a number in brackets. For example, benzene is [6]annulene, and 1,3,5,7-cyclooctatetraene is [8]annulene.
    Annulene
  16. A planar cyclic conjugated system that is stabilized by electron delocalization; its pi electron energy is less than that of a corresponding open-chain compound; it has a large resonance energy; it reacts by substitution rather than addition; in the lH NMR spectrum, protons exterior to the ring are deshielded.
    Aromatic
  17.  A planar cyclic conjugated ion that is stabilized by electron delocalization, and its pi electron energy is less than that of a corresponding open-chain ion
    Aromatic ion
  18. A planar cyclic conjugated system that is destabilized by electron delocalization, and its pi electron energy is greater than that of a corresponding open-chain compound.
    Antiaromatic
  19. A cyclic conjugated system (usually not planar) whose pi electron energy is the same as that of the corresponding open-chain compound.
    Nonaromatic
  20.  A class of aromatic compounds whose molecules have two or more benzene rings fused together. Also called polycyclic benzenoid aromatic hydrocarbons.
    Benzoid aromatic compound
  21. An aromatic compound that does not contain any benzene rings, such as azulene.
    Nonbenzoid aromatic compound
  22.  A class of aromatic compounds with an even number of carbon atoms, which form a cage-like fused-ring polycyclic system with twelve five-membered rings and the rest six-membered rings. For example, [60]fullerene has the geometry of a truncated icosahedron and is called buckminsterfullerene.
    Fullerene
  23. A form of elemental carbon composed of a cylindrical cluster of carbon atoms
    Nanotube
  24. A cyclic compound that has an element other than carbon in an aromatic ring; the most common heteroatoms are N, O and S
    Heterocyclic aromatic compound

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