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Chapter 17 Know what pKa means? QUESTION: If I have a high pKa will I dissociates easily? Know what electron inductive effects do (below) QUESTION: Place in order of the pKa from high to low. O H O H H3C O H CH3 O2N CH3 NO2 NO2 Hydromecuration –Synthesis of Alcohols from an Alkene (Markinov) H H H HO 1) Hg(OAc)2, H2O, THF 2) NaBH4 H H CH 3 CH 3 Hydroboration – Synthesis of Alcohols from an Alkene (Anti-Markinov) H H H H H 1) BH3, THF 2) -OH, H2O2 H H OH H H 1,2 Diol Synthesis with Osium tetraoxide (Syn Addition) CH 3 CH 3 OH O O Os O O + pyridine OH or OsO 4 Reduction of and Ketone or Aldehyde using Sodium Borohydride to form and Alcohol. O OH 1) NaBH4, ethanol 2)H3O+ Reduction of and Ketone or Aldehyde using Lithium Aluminum Hydride to form and Alcohol. O OH 1) LiAlH4, ether 2)H3O+ GRINGARD SYNTHESIS (KNOW THIS) OH Br MgBr Mg O + O Mg Br MgBr QUESTION: Do this reaction MgBr O + Dehydration Base Catalyzed OH KOH + OH Acid Catalyzed OH H3O+ Phosphorus oxychloroide OH POCl 3 Oxidation of Alcohols With PCC