l9 - Electrophilic Aromatic Substitution Reactions SO3...

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Br B Electrophilic Aromatic Substitution Reactions Br-Br / FeBr 3 H + Br-FeBr 3 Br SO 3 H 2 SO 4 SO 3 H Cl-Cl / AlCl 3 Cl O CH 3 -Cl / AlCl 3 CH 3 Cl CH 3 AlCl 3 HNO 3 H 2 SO 4 Friedel Crafts Alkylation C CH 3 O NO 2 Friedel Crafts Acylation
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Now that we have all our reactions, lets summarize activation and deactivation Electron Withdrawing Groups deactivate the ring B C N O O H N O O SO 3 H NH 3 NH 2 Best H + aniline anilinium O O CH 3 H O R O HN O CH 3 A. EDG or B EWG ? 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 O O pk a = 7.15 H 3 C H 3 C pk a = 10.21 Predict pKa A less than 10 B greater than 10 A. less than 10 B. greater than 10
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OH O X X -X pK a -H 9.99 H -NO 2 -OCH 3 7.15 10.21 O O O O -CH 3 -CN COCH 10.26 8.61 8 05 -COCH 3 -CF 3 -F 8.05 8.68 9 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 effect resonance effect Cl poor at bonding π 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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Friedel Crafts Difficult or impossible
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