lecture 22.1

lecture 22.1 - 22-22-1Organic Organic...

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Unformatted text preview: 22-22-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson22-22-2Reactions of Reactions of Benzene and itsBenzene and itsDerivativesDerivativesChapter 22Chapter 2222-22-3Reactions of BenzeneReactions of BenzeneThe most characteristic reaction of aromatic compounds is substitution at a ring carbon++ChlorobenzeneHalogenation:HClCl2Fe Cl3HCl++NitrobenzeneNitration:HNO2HNO3H2SO4H2O22-22-4Reactions of BenzeneReactions of Benzene+Benzenesulfonic acidSulfonation:HSO3HSO3H2SO4++An alkylbenzeneAlkylation:RRXAlX3HX++Acylation:An acylbenzeneHRCXAlX3HXOCROH22-22-5Electrophilic Aromatic SubstitutionElectrophilic Aromatic SubstitutionElectrophilic aromatic substitution:Electrophilic aromatic substitution:a reaction in which a hydrogen atom of an aromatic ring is replaced by an electrophileWe studyseveral common types of electrophiles how each is generatedthe mechanism by which each replaces hydrogen++HEE+H+22-22-6ChlorinationChlorinationStep 1: formation of a chloronium ionStep 2: attack of the chloronium ion on the ring+++Resonance-stabilized cation intermediate; the positivecharge is delocalized onto three atoms of the ring+slow, ratedeterminingClHHClHClClClClClClClFeClClClFeClClClFeCl4-+-A molecular complex with a positive charge on chlorineFerric chloride(a Lewis acid)Chlorine(a Lewisbase)++An ion pair containing a chloronium ion22-22-7ChlorinationChlorinationStep 3: proton transfer regenerates the aromatic character of the ringClHCl-FeCl3ClHClFeCl3ChlorobenzenefastCation intermediate+++-+22-...
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lecture 22.1 - 22-22-1Organic Organic...

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