eas - EFFECT OF AROMATIC STABILIZATION ON REACTIONS OF...

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EFFECT OF AROMATIC STABILIZATION ON REACTIONS OF BENZENE (and other aromatic compounds) ADDITION Bonds Bonds 2 2 No reaction Br Br exothermic would be Br broken made Br bond (65 kcal/mol)) 2 C-Br Br-Br (2 x 70 (50 kcal/mol) kcal/mol) bond 2 C-Br Br-Br bond endothermic also would loose AROMATIC STABILIZATION INSTEAD - SUBSTITUTION 3 / 2 FeBr Br Br p p
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Aromatic compounds like benzene undergo SUBSTITUTION Instead of ADDITION For bromination E + = Br-Br + FeBr 3
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Energy Diagram for Bromination
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ELECTROPHILIC SPECIES IN EAS Br 2 /FeBr 3 Br HNO 3 /H 2 SO 4 NO 2 D 2 O/D 2 SO 4 D O R Cl AlCl 3 R Cl O AlCl 3 OR Cl 2 /AlCl 3 for Cl FeBr 3 Br Br O N O D R O R O ELECTROPHILE nitronium ion deuterium ion carbocation acylium ion
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+ Nitronium O=N=O Benzene + Acylium CH 3 C=O
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Summary of Directing Effects Four categories: I. Strongly activating, ortho/para directing (eg. -OMe) II. Weakly activating, ortho/para directing (eg. -CH 3 ) III. Weakly deactivating, ortho/para directing (eg. -Cl,) IV. Deactivating, meta directing (eg. -NO 2 )
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I. Strongly activating, ortho/para directing (LP electrons)
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eas - EFFECT OF AROMATIC STABILIZATION ON REACTIONS OF...

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