Chapter 21

Chapter 21 - 1 CHEM 262 Wei You Chapter 22. Reaction of...

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Unformatted text preview: 1 CHEM 262 Wei You Chapter 22. Reaction of Benzene and its Derivatives (1) Electrophilic Aromatic Substitution (EAS) a hydrogen atom of an aromatic ring is replaced by an electrophile + + H E E + H + + E + H E H + slow, rate determining Step 1: Step 2: E H + fast + H + E Electro- phile Resonance-stabilized cation intermediate Via... 2 EAS Rxns of Benzene + Benzenesulfonic acid Sulfonation: H SO 3 H SO 3 H 2 SO 4 + + An alkylbenzene Alkylation: R RX AlX 3 HX + + Acylation: An acylbenzene H RCX AlX 3 HX O CR O H 3 EAS Rxns of Benzene Contd + + Chlorobenzene Halogenation: H Cl Cl 2 FeCl 3 HCl + + Nitrobenzene Nitration: H NO 2 HNO 3 H 2 SO 4 H 2 O 4 Chlorination + + + Resonance-stabilized cation intermediate; the positive charge is delocalized onto three atoms of the ring + slow, rate determining Cl H H Cl H Cl Cl Cl Cl Cl Cl Cl Fe Cl Cl Cl Fe Cl Cl Cl FeCl 4- +- A molecular complex with a positive charge on chlorine Ferric chloride (a Lewis acid) Chlorine (a Lewis base) + + An ion pair containing a chloronium ion 5 Chlorination Mech Contd...
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This note was uploaded on 03/22/2009 for the course CHEM 262 taught by Professor Forbes during the Spring '08 term at UNC.

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Chapter 21 - 1 CHEM 262 Wei You Chapter 22. Reaction of...

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