Lecture 20 Outline of Last Lecture I Addition to Alkenes II Regioselective Addition of HX 1 III Acid Catalyzed Hydration 2 IV Addition of Cl2 or Br2 3 Outline of Current Lecture CHEM 333 1st Edition I Br2 or Cl2 addition in the presence of H2O or R OH 4 II Oxymercuration Reduction 5 III Hydroboration Oxidation 6 IV Oxidation 7 V Ozonolysis Current Lecture I Br2 or Cl2 addition in the presence of H2O or R OH 4 a Example i Mechanism b Regioselective reaction X adds to less substituted side of doube bond OH adds to more substituted side of double bond X and OH are anti to each other i Example c Can substitute H2O with an alcohol R OH i Example d Can have internal attack of an alcohol onto a brominium chlorinium ion to make a 5 or 6 membered ring i Example II Oxymercuration Reduction 5 hydration of an alkene a Example b Example c Example goes through carbocation Look for rearrangements d Example no carbocation so no rearrangement III Hydroboration Oxidation 6 anti Markovnikov addition of OH across a double bond a Example b Example c Example IV Oxidation 7 a OsO4 osmium tetroxide oxidation of an alkene to a 1 2 diol b Example V Ozonolysis cleavage of a cdouble bond to 2 carbonyls a Example b Example
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