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