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11-06 - 1 Alkene Additions CH 3 H H H H OH H 2SO4 H 2O 63...

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Unformatted text preview: 11/6/2009 11/6/2009 1 Alkene Additions CH 3 H H H H OH H 2SO4 H 2O 63 63 Regiochemistry of halohydrin formation 64 64 weaker bond weaker bond “Br-OH”, “Cl-OH” undergo anti- addition Br H 2 O Br-Br H 3 C H 3 C 65 65 2.03Å 2.03Å 2.17Å 2.17Å 2.06Å 2.06Å Alkene Additions CH 3 H H H H OH H 2SO4 H 2O 66 66 CH 3 H H H Br OH Br 2/H2O Roadmap Problems Roadmap Problems A B E 67 67 A B D C F CH 3 HBr HBr . A. B. 68 68 Which is the correct product? 11/6/2009 11/6/2009 2 CH 3 HBr HBr . CH 3 OH Which is the correct product? Which is the correct product? 69 69 CH 3 OH A. A. B. B. C. C. CH 3 HBr HBr . CH 3 OH 1. BH 3 2. H 2O2/- OH 1. BH 3 2. H 2O2/- OH + + enantiomer enantiomer 70 70 Alkene Additions 71 71 osmate ester osmium tetroxide ethylene glycol syn-addition 72 72 OH HO A. B. C. both syn addition Which product(s) will form? OsO 4 O Os O O O NaHSO 3 H 2 O OH HO racemic racemic mixture mixture 73 73 meso meso Give a synthesis of 3,4-heptanediol.- Start with any compound containing four carbons or less. - Use any inorganic reagents necessary. 1. OsO4 What is the best last step? A. i B. ii C. i or ii H HO OH H 74 74 2. NaHSO3/H2O 1. OsO4 2. NaHSO3/H2O i ii 11/6/2009 11/6/2009 3 Alkene Additions CH 3 H H H H OH H 2SO4 H 2O 75 75 CH 3 H H H Br OH Br 2/H2O C H H Addition of divalent carbon (carbene) to alkenes diiodomethane...
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