Aromatic Substitution
A 24-module path through aromatic substitution, in study order from foundations to the frontier.
Modules
- Aromaticity and the Special Stability of Benzene
- Why Benzene Reacts by Substitution, Not Addition
- The General Mechanism of Electrophilic Aromatic Substitution
- The Arenium Ion (Sigma Complex) Intermediate
- The Energy Diagram of Electrophilic Aromatic Substitution
- Aromatic Halogenation
- Nitration of Benzene
- Sulfonation of Benzene and Its Reversibility
- Friedel-Crafts Alkylation
- Limitations of Friedel-Crafts Alkylation
- Friedel-Crafts Acylation
- Acylation-Then-Reduction to Make Alkylbenzenes
- Activating and Deactivating Substituents
- Substituent Effects on Reaction Rate
- Inductive vs Resonance Effects of Substituents
- Explaining Directing Effects Through Intermediate Stability
- Ortho/Para Directors
- Meta Directors
- Halogens as Deactivating Ortho/Para Directors
- Ortho vs Para Selectivity
- Directing Effects in Disubstituted Benzenes
- Using a Sulfonic Acid Group as a Blocking Group
- Nucleophilic Aromatic Substitution (Addition-Elimination)
- The Benzyne Mechanism (Elimination-Addition)