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Quiz yourself by thinking what should be in each of the black spaces below before clicking on it to display the answer.
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Question
Answer
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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