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Reactions of Benzene & Its Derivatives

Organic Lecture Series1 Reactions of Reactions of Benzene & Benzene & Its DerivativesIts DerivativesChapter 22 Organic Lecture Series2 Reactions of BenzeneReactions of BenzeneThe most characteristic reaction of aromatic compounds is substitution at a ring carbon:++ChlorobenzeneHalogenation:HClCl 2 FeCl3 HCl++NitrobenzeneNitration:HNO2 HNO3H2SO4H2 OOrganic Lecture Series3+Benzenesulfonic acidSulfonation:HSO3 HSO3H2SO4++An alkylbenzeneAlkylation:RRXAlX3HX++Acylat ion:An acylbenzeneHRCXAlX3 HXOCROHR eactions of BenzeneReactions of BenzeneOrganic Lecture Series4 RArenesAlkylbenzenesAlCl3 RClCarbon-Carbon Bond Formations:Organic Lecture Series5 Electrophilic Aromatic SubstitutionElectrophilic Aromatic Substitution Electrophilic aromatic substitution:Electrophilic aromatic substitution: a reaction in which a hydrogen atom of an aromatic ring is replaced by an electrophile In this section: several common types of electrophiles how each is generated the mechanism by which each replaces hydrogen++HEE+H+Organic Lecture Series6 EAS: General MechanismEAS: General Mechanism A general mechanism Key question: What is the electrophile and how is it generated?

Its Derivatives Chapter 22 Organic Lecture Series 2 Reactions of Benzene The most characteristic reaction of aromatic compounds is substitution at a ring carbon: + + Chlorobenzene Halogenation: H Cl2 Cl FeCl3 HCl + + Nitrobenzene Nitration: HNOHNO3 2 H2 SO4 H2 O. Organic Lecture Series 3 + Benzenesulfonic acid Sulfonation: HSOSO3 3 H H2 SO4 ...

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