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Reactions
Question | Answer |
---|---|
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 |