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Lecture Notes for CHE 232 - ORGANIC CHEMISTRY II with Anthony at Kentucky (UK)

Notes Information

Material Type:Class Note
Professor:Anthony
Class:CHE 232 - ORGANIC CHEMISTRY II
Subject:Chemistry
University:University of Kentucky
Term:Fall 2004
Keywords:
  • Particularly
  • Electrophile
  • Substitution
  • Degradation
  • Aromatic Ring
  • Withdrawing
  • Hydrogenation
  • Antibiotics
  • Recognition
  • Substitutions
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Sample Document Text

Reactions of Aromatic Compounds Simple alkenes tend to undergo addition reactions: HBrBr 2 Br Br Br C 3 H 6 C 3 H 6 Br 2 C 3 H 7 Br The elements of the reagent (HBr or Br 2 ) are simply added to the starting material. This is caled, unsurprisingly, and addition reaction. Aromatic compounds do not react in this manner. A look at a simple aromatic bromination: Br 2 / FeBr 3 Br C 6 H 6 C 6 H 5 Br What we have done in this case is substitute a bromine for a hydrogen. Hence the term "aromatic substitution." Because the benzene ring is quite electron-rich, it almost always behaves as the nucleophile in a reaction - which means that the substitution on benzene occurs by the addition of an electrophile -> electrophilic aromatic substitution. There is basicaly one simple mechanism for al electrophilic aromatic substitutions: E + H E H E H E B - E The benzene acts as a nucleophile, atacking the electrophile with a pair of its ?-elec...

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