Chapter 22-1

Chapter 22-1 - 11 CHEM 262 Wei You Chapter 22. Reaction of...

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Unformatted text preview: 11 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... 22 Click to edit Master subtitle style Opens up a lot of opportunities! 33 Typical EAS + Benzenesulfonic acid Sulfonation: SO 3 SO 3 2 S 4 + + An alkylbenzene Alkylation : X A l X 3 HX + + Acylation : An acylbenzene H R X l X 3 X O CR O 44 Typical EAS + + Chlorobenzene Halogenation: H Cl Cl 2 FeCl 3 HCl + + Nitrobenzene Nitration: H NO 2 HNO 3 H 2 SO 4 H 2 O 55 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 66 Chlorination Mech Contd...
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This note was uploaded on 06/12/2010 for the course CHEM 261 taught by Professor Austell during the Spring '08 term at UNC.

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Chapter 22-1 - 11 CHEM 262 Wei You Chapter 22. Reaction of...

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