Chapter 19 Aromatic Compounds and Benzene Derivatives

Benzene and derivatives are aromatic hydrocarbons with one ring or several rings fused together. The aromatic character of benzene and derivatives have special stability, which imparts a unique chemical profile. The delocalized bonding in benzene is not properly described by a structure that shows localized single and double bonds. Two structures are needed to properly represent benzene, with a double-headed arrow to show they are resonance contributors. In benzene derivatives one or more hydrogen atoms have been replaced with alkyl groups, heteroatom substituents, or functional groups. Dimethylbenzene is an arene with two substituents on the ring and has the common name xylene.

Structure of Benzene

Hilckel's rule

Nomenclature of Arenes

Nomenclature of Functionalized Benzene Derivatives

Electrophilic Aromatic Substitution

Halogenation, Nitration and Sulfonation

Friedel-Crafts Alkylation

Friedel-Crafts Acylation

Regioselectivity

Predicting Regioselectivity

Activating and Deactivating Groups

S,Ar Reactions of Halobenzenes

S,Ar Reactions of Aniline

S,Ar Reactions

S,Ar Reactions of Disubstituted Benzenes

Reduction of Benzene Derivatives

Aromatic Compounds

Polycyclic Aromatic Compounds

Nucleophilic Aromatic Substitution

Benzyne Intermediates

Diazonium Salts

Reactions of Diazonium Salts

Spectroscopy of Benzene Derivatives

Synthesis of Benzene Derivatives

Aromatic Coupling Reactions

Polycyclic Aromatic Hydrocarbons (PAH)