26. Aromatic Substitution in Synthesis: Friedel-Crafts and Moses Gomberg

Freshman Organic Chemistry II (CHEM 125B)

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.

00:00 - Chapter 1. Discovery of Friedel-Crafts Alkylation and Acylation
13:26 - Chapter 2. Avoiding Friedel-Crafts Rearrangements
19:48 - Chapter 3. Synthetic Accessibility via Aromatic Substitution. Diazonium Salts
35:15 - Chapter 4. Nucleophilic Aromatic Substitution and NADH Reduction
40:44 - Chapter 5. Benzylic Reactivity, Steric Hindrance, and Moses Gomberg


Complete course materials are available at the Open Yale Courses website: http://oyc.yale.edu

This course was recorded in Spring 2011.