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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 substitutio

• Friedel-Crafts alkylation forms a new C-C bond between an aromatic ring and an alkyl group Cl AlCl3 + HCl Benzene 2-Chloropropane (Isopropyl chloride) Cumene (Isopropylbenzene) + The electrophilic partner is a carbocation; it will arrange to the most stable ion: allylic>3o>2o>1o.

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  Alkylation

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