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OChem Ex3

Exam 3

TermDefinition
Hydrohalogenation - HCl, HBr, HI H + X is added X= Cl, Br, I regio: markovnikov - HBr/ROOR H + Br is added Regio: anti-markovnikov NONE: stereo
Acid Catalyzed Hydration H2SO4 (dil) or H2SO4/H2O or H3O+ H + OH is added Regio: markovnikov stereo: none
Oxymercuration Demercuration 1. Hg(OAc)2, H2O/ 2. NaBH4 H+OH is added regio: markovnikov Stereo: anti
Hydroboration Oxidiation 1. B2H6/2. H2O, NaOH or 1.BH3 * THF/2. H2O2, NaOH H+OH is added regio: antimarkovnikov Stereo: syn
Acid-Catalyzed Addition of an Alcohol H2SO4 (dil)/CH3OH H+OR is added regio: markovnikov stereo: none (similar to acid-catalyzed addition hydration)
Alkoxymercuration-demercuration 1. Hg(OAc)2, CH3OH/2. NaBH4 H+OR is added regio: markovnikov stereo: anti (similar to oxymercuration-demercuration)
Catalyitc Hydrogenation H2/Catalyst (Catalyst can be Pd, Pt, Ni) H+H is added regio: n/a stereo: syn
Halogenation Br2/inert solvent (CCl4 or CH2Cl2) X+X is added regio: n/a Stereo: anti (3-member ring w/ backside attack on sp3-carbon)
Halohydrin Formation X2/ H2O or ROH X+ OH or OR is added regio: markovnikov stereo: anti (halogen gets added as attacking alkene)
Epoxidation Anti-dihydroxylation RCO3H or 1.MCPBA/2.H3O+ For expoxidation: oxygen is added regio: n/a stereo: syn For anti-dihydroxylation: OH+OH is added regio: n/a Stereo: anti
Syn-dihydroxylation OH+OH is added regio: n/a stereo: syn
Created by: ariver
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