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Lecture Notes for CHEM 542 - Organic Reaction Mechanisms at Bowling Green (BGSU)

Notes Information

Material Type:Class Note
Professor:Staff
Class:CHEM 542 - Organic Reaction Mechanisms
Subject:Chemistry
University:Bowling Green State University
Term:--
Keywords:
  • Particularly
  • Interrupting
  • Acetylation
  • Substitutions
  • Electrophile
  • Substitution
  • Deactivation
  • Aromatic Ring
  • Interesting
  • Hydrocarbons
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Lecture 23 / 1 Chapter 7. Aromatic substitutions Aromaticity Aromatic compounds: cyclic flat structures with conjugated C=C bonds. According to HMO theory an aromatic molecule is one that follows Huckel's rule (4n+2 ?-electrons in a single ring of conjugated ?-bonds). Aromaticity is characterized by a) a delocalization (resonance) ?-bond energy that is lower than the sum of the energies of the component ?-bonds, and b) equal/average bond lengths between the ring atoms, rather than alternating single and double bonds. a) is determined from calorimetry, while b) is obtained from numerous spectroscopic observations and X-ray diffraction. NMR: diatropic compounds: ability to sustain a diamagnetic ring current. Experimental proof of aromaticity: 1) induced ring current, 2) equal bond distances, 3) planarity (although there are spherical aromatic molecule, see fullerenes), 4) chemical stability, 5) ability to undergo aromatic substitutions. In contrast to stable aromatic molecules...

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