Lecture4-ElectrophilicAromaticSubstitution(1)-1

Lecture4-ElectrophilicAromaticSubstitution(1)-1 -...

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9/21/11 Announcements v Review session today 4:00-6:00 pm in Javits 100. Dave and Ida will host. v Office hours today: 2:00-4:00 pm (normal time). v Exam I Room Assignments v Last Names: A – K Javits 102 v Last Names: L – Z Harriman Hall 137 v Exam I Material: v Chapters 13-15, Study Guides 1 (page 1 only) & 2. v Exclude: 14.7C, 14.10, 14.11, 15.13D, paragraph of p. 618, and 3 reactions on top of p. 685. 11
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9/21/11 More Announcements v What to Bring to Exam I: v One 5” x 8” card. You can write whatever you want on this card (front and back). Please put your name and ID. No xeroxed or typed pages allowed. v Pencils with erasers v Molecular model kit v A photo ID card v Stony Brook ID # - Very important!! v Exam I – 9:30 – 11:15 am. If you arrive after 9:50 am, you will NOT be allowed to take the exam! 22
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9/21/11 Exam Rules v Restroom breaks only allowed between 9:50 – 10:50 am. v If you finish early, you must wait until 10:50 am to leave. v If you continue to write after exam time, a 5-point penalty will be applied to your exam. v Don’t cheat. I don’t feel like dealing with Academic Judiciary. 33
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9/21/11 heat 44 Predict the product of this Diels-Alder Reaction. 5 4 3 2 1 6 7 8 9 1 0 5 4 3 2 1 6 7 8 9 1 0 A B C 1 1 1 2 1 3 1 4 1 1 1 2 1 3 1 4 D E
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9/21/11 Select the fastest reaction. 55 HO NH 2 NH 2 + NH 2 NH 2 HO NC + NC O O F + F + H 3 CO O O H 3 CO O O A D C B
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9/21/11 Review: Electrophilic Aromatic Substitution 66 E E H E E H E H E H A
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9/21/11 Review: Reactions Summary 77 Br 2 FeBr 3 Br Cl 2 FeCl 3 Cl or AlCl 3 I 2 HNO 3 I SO 3 H 2 SO 4 SO 3 H conc. HNO 3 H 2 SO 4 NO 2 heat
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9/21/11 Review: Halogenation 88 Br 2 FeBr 3 Br Br Fe Br Br Br Br Br Br Fe Br Br Br Br Fe Br Br Br Br H Br +
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9/21/11 Review: Reactions Summary 99 Br 2 FeBr 3 Br Cl 2 FeCl 3 Cl or AlCl 3 I 2 HNO 3 I SO 3 H 2 SO 4 SO 3 H conc. HNO 3 H 2 SO 4 NO 2 heat
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9/21/11 Review: Nitration 1010 + HNO 3 H 2 SO 4 NO 2 heat O S H O O O H O N O O H O N O O H H pKa = -9 pKa = -1.4 Nitronium Ion (Electrophile) H N O O N O O H O H N O O =
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9/21/11 Review: Reactions Summary 1111 Br 2 FeBr 3 Br Cl 2 FeCl 3 Cl or AlCl 3 I 2 HNO 3 I SO 3 H 2 SO 4 SO 3 H conc. HNO 3 H 2 SO 4 NO 2 heat 1) H 2 SO 4 , H 2 O, heat 2) OH - SO3H group could be used as a blocking group.
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9/21/11 1212 R-Cl AlCl 3 R Rearrangements can occur. Not synthetically applicable. Review: Reactions Summary Friedel-Crafts Alkylation CH 3 -Cl AlCl 3 3 AlCl 3 Cl
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9/21/11 1313 Cl Al Cl Cl H 3 C Cl H 3 C Cl Cl Cl Cl Al CH 3 H 3 + 3 -Cl AlCl 3 3 Review: Friedel-Crafts Alkylation (1o substrate) SN2 attack Al
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9/21/11 1414 Cl Al Cl Cl Cl Cl Al Cl Cl Cl Cl Al H + AlCl 3 Cl Review: Friedel-Crafts Alkylation (2o/3o substrate) SN1 attack
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9/21/11 1515 R-Cl AlCl 3 R Rearrangements can occur. Not synthetically applicable. Review: Reactions Summary Friedel-Crafts Alkylation CH 3 -Cl AlCl 3 3 AlCl 3 Cl
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9/21/11 1616 Cl Al Cl Al Al H + AlCl 3 Cl Review: Friedel-Crafts Alkylation (1o substrate) SN2 attack (Hydride Shift) Cl Al H SN1 attack
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9/21/11 Predict the major product.
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This note was uploaded on 09/21/2011 for the course CHEM 213CCF taught by Professor Staff during the Spring '08 term at Pennsylvania State University, University Park.

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Lecture4-ElectrophilicAromaticSubstitution(1)-1 -...

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