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Notes2_AdditiontoPiLecture

Notes2_AdditiontoPiLecture - Cis/Trans E and Z H C R C H R...

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Cis/Trans, E and Z? C C H R H R C C H R R H C C H Cl H H 3 C C C CH 2 CH 3 H H H 3 C C C CH 2 CH 3 Cl H H 3 C Trans Cis Trans Cis The Alkyl groups are cis The proper IUPAC name is with E/Z nomenclature E Copyright © 2008 Stephanie L. Gould
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C C Cl H Br High High E Copyright © 2008 Stephanie L. Gould
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Addition to Carbon-Carbon Pi Bonds Lecture Supplements: pg. 21‐24 CFC, OWLS, PP: pg. 144‐168 Vollhardt: Chapter 12, SecQons 12‐1 to 12‐8, 12‐12 Chapter 13, SecQon 13‐7 Klein: Chapter 11 (OpQonal) All materials herein are copyright © 2008 Stephanie L. Gould. Materials are intended for personal use in conjuncQon with Chemistry 14D at UCLA. DistribuQon is not permi\ed.
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Alkenes and Alkynes Alkene, one sigma bond, one pi bond Alkyne, one sigma bond, two pi bond This topic will deal with addiQon to the pi bonds Figure from Vollhardt pg. 37 See Vollhart pg. 37 Copyright © 2008 Stephanie L. Gould
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Alkenes in Everyday Life C C H H H H C C H CH 3 H H C C H Cl H H Ethylene (polyethylene) Vinyl Chloride (polyvinyl chloride, PVC) Propylene (polypropylene) Monomers of common plasQcs C C Cl Cl Cl Cl tetrachloro ethylene "perc" Industrial Cleaners Natural AnQoxidants (Lycopene) Copyright © 2008 Stephanie L. Gould
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Generalized Addition to Pi Bonds Rxn C C R R R R electrophile R R R R E nucleophile R R R R E N Components – Alkene, Electrophile, Nucleophile ConsideraQons – 1) Electrophile AddiQon site 2) Nucleophile AddiQon OrientaQon with respect to Electrophile Copyright © 2008 Stephanie L. Gould
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Addition to C=C 1) AddiQon of HX to ‐C=C‐ and ‐C C‐ ** 2) AddiQon of Halogens (X 2 ) to ‐C=C‐ and ‐C C‐ ** 3) Alcohol FormaQon from Alkenes 1) Acid Catalysis ** 2) OxymercuraQon/DemercuraQon 3) HydroboraQon/OxidaQon 4) HydrogenaQon 5) Ozonolysis ** You should know these mechanisms. Knowing the mechanisms of the other reacQon will help you understand the major product. Knowing the major product is required, the mechanisms for non‐stared rxns are not required. Copyright © 2008 Stephanie L. Gould
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Addition of HX to –C=C- C C R R R R electrophile R R R R E nucleophile R R R R E N X = Cl, Br, I H X δ δ + Copyright © 2008 Stephanie L. Gould
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Energy Diagram Reaction Coordinate Reactant/ Reagent AddiQon Product CarbocaQon [TS 1 ] [TS 2 ] E a 2 E a 1 Copyright © 2008 Stephanie L. Gould
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Regioselective Nature of Addition H Br C C H H C C H H H + Br - C C H H H Br Major Intermediate Minor Intermediate C C H H H + Br Copyright © 2008 Stephanie L. Gould
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Markovnikov’s Rule Discovered by Vladimir Vasilyevich Markovnikov in 1850: When a hydrogen halide adds to an alkene the
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