Chem 336 - Spring 1999 - Organic Chemistry III
Portland State University - Dr. Carl C. Wamser

Chapter 20 - Aromatic Substitution Reactions

Electrophilic Aromatic Substitution

Mechanism of Aromatic Substitution

Mechanism - why slower than alkenes ?

Mechanism - why substitution ?

Bromination of Benzene

Chlorination of Benzene

Nitration of Benzene

Sulfonation of Benzene

Friedel-Crafts Alkylation

Friedel-Crafts Acylation

Substituent Effects

Reactivity Effects

Orientation Effects

Ortho, Para Directors

Meta Directors

Classifying Substituents

Synthetic Strategy

Synthesis Example

Synthesis Example

Nucleophilic Aromatic Substitution - Benzyne (Elimination/Addition)

Nucleophilic Aromatic Substitution - Anion Intermediate (Addition/Elimination)