CHEM 125A: FRESHMAN ORGANIC CHEMISTRY II - Lecture 26 - Professor J. Michael McBride
Aromatic Substitution in Synthesis: Friedel-Crafts and Moses Gomberg
The Friedel-Crafts reaction creates new alkyl- or acyl-aromatic bonds,
with or without cation rearrangement. Designing reaction sequences,
especially those involving diazonium intermediates, so as to access a
wide variety of substituted benzenes provides a good introduction to the
challenges of synthetic organic chemistry. Aromatic rings with strong
electron withdrawal can undergo nucleophilic aromatic substitution,
which plays an important role in biochemistry. The special properties of
phenyl-substituted alkanes, especially benzylic reactivity and steric
hindrance, played an important role in the development of organic
chemistry a century ago.
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