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Notes_EASLecture

Notes_EASLecture - Electrophilic Aromatic Substitution...

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Electrophilic Aromatic Substitution Vollhardt: Chapter 15: Sec2ons 15‐8 to 15‐13 Chapter 16: Sec2ons 16‐1 to 16‐4, 16‐6 and 16‐7 Lecture Supplements: pg. 25‐28 CFC, OWLS, PP: pg. 169‐193 All materials herein are copyright © 2008 Stephanie L. Gould. Materials are intended for personal use in conjunc2on with Chemistry 14D at UCLA. Distribu2on is not permiTed.
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General Reaction H Electrophile Electrophile Things to consider: *Electrophile takes the place of a hydrogen (Subs2tu2on) *Aroma2c ring that is in the reactants is s2ll an aroma2c ring in the product Copyright © 2008 Stephanie L. Gould
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Why not a “regular” Addition Reaction? HBr Br H Br 2 Br Br Br Br + vs. HBr or Br 2 No Reaction Stabiliza2on from conjuga2on (special type of aroma2city) Copyright © 2008 Stephanie L. Gould
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Figures from Vollhardt pg. 37 and 670 Refer to your 14C notes! Copyright © 2008 Stephanie L. Gould Figure from Vollhardt, pg. 37 Figure from Vollhardt, pg. 670
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General Reaction Mechanism E + H H H H E H H E H H E Step 2: H H E B H E + HB Step 3: Step 1: Makes the electrophile more electrophilic Arenium Carboca2on Copyright © 2008 Stephanie L. Gould
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Energy Diagram Figures from Vollhardt pg. 694 Copyright © 2008 Stephanie L. Gould Figure from Vollhardt, pg. 694
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6 Common EAS Reactions 1) Halogena2on (Br 2 and Cl 2 ) 2) Nitra2on 3) Sulfona2on 4) Friedel‐Craas Acyla2on 5) Friedel‐Craas Alkyla2on 6) Diazoniza2on of a Primary Amine NOTE: All mechanisms in this sec2on are considered important for you to know Copyright © 2008 Stephanie L. Gould
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General Reaction Mechanism E + H H H H E H H E H H E Step 2: H H E B H E + HB Step 3: Step 1: Making the electrophile more electrophilic Arenium Carboca2on Copyright © 2008 Stephanie L. Gould
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Halogenation (Cl 2 or Br 2 ) Br Br FeBr 3 Br Br FeBr 3 Step 2: Step 3: Step 1: H H H H Br Br + H H Br H H Br H H Br H Br + HBr + FeBr 3 Br FeBr 3 Br Br FeBr 3 Br + Br FeBr 3 + Copyright © 2008 Stephanie L. Gould
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Practice the Halogenation Mechanism Cl Cl 2 AlCl 3 Copyright © 2008 Stephanie L. Gould
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Practice the Halogenation Mechanism Step 2: Step 3: Step 1: H H H H Cl H H Cl H H Cl Cl + Cl Cl AlCl 3 Cl Cl AlCl 3 Cl Cl AlCl 3 Cl + Cl AlCl 3 + H H Cl H Cl + HCl + AlCl 3 Cl AlCl 3 Copyright © 2008 Stephanie L. Gould
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EAS Reactions 1) Halogena2on (Br 2 and Cl 2 ) 2) Nitra2on 3) Sulfona2on 4) Friedel‐Craas Acyla2on 5) Friedel‐Craas Alkyla2on 6) Diazoniza2on of a Primary Amine All mechanisms in this sec2on are considered important for you to know Copyright © 2008 Stephanie L. Gould
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Nitration aq. HNO 3 aq. H 2 SO 4 NO 2 N OH O O H OH 2 N OH 2 O O Step 2:
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