Notes_EASLecture

Notes_EASLecture - Electrophilic Aromatic Substitution...

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Unformatted text preview: Electrophilic Aromatic Substitution Vollhardt: Chapter 15: Sec2ons 158 to 1513 Chapter 16: Sec2ons 161 to 164, 166 and 167 Lecture Supplements: pg. 58 CFC, OWLS, PP: pg. 169193 All materials herein are copyright 008 Stephanie L. Gould. Materials are intended for personal use in conjunc2on with Chemistry 14D at UCLA. Distribu2on is not permiTed. 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 008 Stephanie L. Gould 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 008 Stephanie L. Gould 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 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 Carbocaon Copyright 2008 Stephanie L. Gould Energy Diagram Figures from Vollhardt pg. 694 Copyright 2008 Stephanie L. Gould Figure from Vollhardt, pg. 694 6 Common EAS Reactions 1) Halogena2on (Br and Cl ) ) Nitra2on 3) Sulfona2on 4) FriedelCraAs cyla2on 5) FriedelCraAs lkyla2on 6) Diazoniza2on of a Primary mine NOTE: ll mechanisms in this sec2on are considered important for you to know Copyright 008 Stephanie L. Gould 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 Carbocaon Copyright 2008 Stephanie L. Gould 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 Practice the Halogenation Mechanism Cl Cl 2 AlCl 3 Copyright 2008 Stephanie L. Gould 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 EAS Reactions 1) Halogena2on (Br and Cl ) ) Nitra2on 3) Sulfona2on 4) FriedelCraAs cyla2on 5) FriedelCraAs lkyla2on 6) Diazoniza2on of a Primary mine...
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Notes_EASLecture - Electrophilic Aromatic Substitution...

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