l9 - Electrophilic Aromatic Substitution Reactions SO3...

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Electrophilic Aromatic Substitution Reactions Br-Br / FeBr 3 Br H +B r - F e B r 3 Br SO 3 H 2 SO 4 Cl-Cl / AlCl 3 Cl SO 3 H CH 3 -Cl / AlCl 3 Cl CH 3 O AlCl 3 HNO 3 H 2 SO 4 CH 3 Friedel Crafts Alkylation C CH O NO 2 Friedel Crafts Acylation 3
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Now that we have all our reactions, lets summarize ctivation and deactivation activation and deactivation Electron Withdrawing Groups deactivate the ring C N O O H N O O SO 3 H NH 3 NH 2 Best H + niline nilinium O O CH 3 H O R O HN O CH 3 aniline anilinium A. EDG or WG ? Direct substitution meta B. EWG
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OH O O O O pk a =9.99 OH O O OH O N N N O O O O O O pk a =7.15 O O H 3 C H 3 C pk a =10.21 Predict pKa less than 10 B greater than 10 A. less than 10 B. greater than 10
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OH O -X pK a - .99 X X H -NO 2 -OCH 3 9.99 7.15 10.21 O O O O -CH 3 -CN 10.26 8.61 -COCH 3 -CF 3 - 8.05 8.68 89 F δ - inductive F F F resonance F -Cl 9.89 9.41 effect effect
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Cl What about a halide? Does a Cl activate or deactivate the ring? Cl δ - Cl Cl Cl δ + inductive ffect resonance ffect Cl poor at onding effect effect π bonding Deactivates, but directs ortho-para
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Cl HNO 3 H 2 SO 4 Predict the product Cl NO 2 Cl Cl No Reaction NO 2 NO 2 A B C D
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Cl Cl AlCl 3 Predict the product Cl Cl Cl No Reaction A B C D
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riedel Friedel Crafts Difficult or impossible
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This note was uploaded on 04/06/2010 for the course CHE 322 taught by Professor Staff during the Spring '08 term at SUNY Stony Brook.

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l9 - Electrophilic Aromatic Substitution Reactions SO3...

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