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Oxy-demercuration Hg(OAc)2, H20 / NaBH4, NaOH **alkene to alcohol Markovnikov
Hydroboration BH3, THF / H2O2, NaOH **alkene to alcohol anti-Markovnikov
Bromohydrin Br2, H2O **ANTI addition, Br to least substituted
Full hydrogenation H2, Pt
Partial hydrogenation (cis) H2, Ni2 or H2, Pd/CacCO3/quinoline
Partial hydrogenation (trans) Li/NH3
Hydroxylation OSO4/NaHSO3, H20 or KMnO4/cold, dilute **1,2-diols syn-addition
PBr3 OH to Br w/ inversion
SOCl2 OH to Cl w/ inversion
TsCl/pyridine OH to Cl w/o inversion
Alkene to cyclopropyl CH2I2/Zn(Cu)
Alkene to cyclopropyl w/ 2 Cl's CHCl3/tBuOK
Alcohol to asymmetrical ether NaH, THF/other side of ether
Ozonolysis O3, CH2Cl2, -78˚C/Zn, HoAC **alkene to carbonyl
Alkene to epoxides mCPBA
Acid catalyzed ring openings more substituted
Base catalyzed ring openings less substituted
Bromination of alkanes Br2, heat **alkene to leaving group; most stable radical!
Radical addition to alkenes HBr, peroxide **anti-Markovnikov
Radical polymerization of alkenes AIBN or peroxide
Full reduction LAH, i) LiAlH4/ether/ ii) H20
Partial reduction NaBH4/H20 **only aldehydes & ketones
Weaker oxidation PCC **primary OH only aldehydes
Strong oxidation H2CrO4, NaCr2O7, or CrO3/H2SO4 and KMnO4/KOH/H20 **primary OH to carboxylic acid
Created by: 1126089607