Chem 336 - Spring 2000
Organic Chemistry III

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)