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UB CHE 201 8&9A

Alkene and Alkyne. Given Reactant and Reagent Give Product

alkene + H-X markovnikov alkyl halide
alkene + H-Br --peroxides-> anti-markovnikov alkyl halide
alkene + water --H+-> markovnikov alcohol
alkene + 1)BH3*THF, 2)H2O2, OH- anti-markovnikov alcohol
alkene +H2 --Pt,Pd, or Ni-> syn addition alkane
alkene + X2 anti addition alkyl dihalide
alkene + peroxyacid syn addition epoxide + carboxylic acid
epoxide ---H+, H2O-> anti glycol
alkene ---1)peroxyacid, 2)H+, H2O-> anti glycol
alkene + KMnO4 (cold, dilute) ---OH-, H2O-> syn glycol
alkene + OsO4 ---H2O2 -> syn glycol
alkene + O3 ozonide
ozonide --(CH3)2S ketones and aldehydes
alkene + KMnO4(warm) ketones and acids
acetylide + NaNH2 acetylide anion + Na+ + NH3
acetylide anion + R-X alkyne molecule with desired R group
acetylide anion + R2C=O alcohol
alkyne + 2H2 --Pt, Pd, or Ni -> alkane
alkyne + H2 ---Pd/BaSO4, quinoline (lindlar's catalyst) --> cis alkene
alkyne -- Na, NH3 --> trans alkene
alkyne + 2X2 haloalkane, 4 halogens
alkyne + 2H-X geminal haloalkane, Markovnikov
alkyne -- HgSO4, H2SO4--> vinyl alcohol <--> ketone , markovnikov
alkyne --1) SiaBH*THF, 2) H2O2, NaOH --> vinyl alcohol <--> aldehyde, anti-markovnikov
alkyne + KMnO4 ---H2O, Neutral -> alpha-diketone
alykne --1) KMnO4, OH-, 2) H+ --> carboxyilic acids
alkyne --O3, H2O --> carboxylic acids
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