Organic Chemistry I:CHEM 2211

Chapter 18

Reactions of Aromatic Compounds

18.1 Electrophilic aromatic substitution

Introduction: substitution and electrophilic activation

Halogenation: Mechanism X+

Nitration & Sulfonation: Mechanism NO2+, SO3H+

Friedel-Craft reaction: C+

Friedel-Craft reaction: C+ property; arrangement

Substituted benzene: Resonance effect and inductive effect

Limitation of Friedel-Crafts Reactions

Friedel-Craft reaction: Intramolecular reaction, synthesis

Introduction: substitution and electrophilic activation

Mechanism:

Mechanism:

Synthesis

Activate or deactive benzene: substitute group effect

Orientation effect: o,p vs m, toluene

Orientation effect: aniline

Orientation effect: NO2

Orientation effect: unique position of halogens

Special things to notice: halogenation of activated benzenes

Synthetic design: watching the orientation effect

oxidation and reduction of substituted benzene: usually forget

Oxidation and reduction of substituted benzene: application in synthesis

Multistep synthesis: practice, practice and practice more