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UB CHE 201 8&9B

Alkene and Alkyne. Given Reactant and Product Give Reagent

alkene --> markovnikov alkyl halide H-X
alkene --> anti-markovnikov alkyl halide H-Br, peroxides
alkene --> markovnikov alcohol H20, H+
alkene ---> anti-markovnikov alcohol 1) BH3*THF, 2) H2O2, OH-
alkene ---> syn addition alkane H2 and Pt, Pd, or Ni
alkene --> anti addition alkyl dihalide X2
alkene ---> anti addition markovnikov halohydrin X2, H20
alkene --> epoxide peroxyacid, example: MCPBA
epoxide --> anti gycol H+, H2O
alkene --> anti glycol 1) peroxyacid, 2) H+ H2O
alkene ---> syn glycol KMnO4 (cold, dilute), OH-, H2O
alkene --> syn glycol OsO4 , H2O2
Alkene -->ozonide O3
ozonide --> ketones and aldehydes (CH3)2S
alkene ---> ketones and aldehydes 1) O3, 2) (CH3)2S
alkene --> ketones and acids KMnO4 (warm)
acetylide ---> acetylide anion NaNH2
acetylide anion --->alkyne R-X
acetylide anion ---> alcohol carbonyl group containing compound (formaldehyde, aldehyde, or ketone)
alkyne ---> alkane 2H2, Pt, Pd, or Ni
alkyne --> cis alkene H2, Pd/BaSO4, quinoline (lindlar's catalyst)
alkyne --> trans alkene Na, NH3
alkyne --> haloalkane (4 X) 2X2
alkyne ---> geminal haloalkane (markovnikov) 2 H-X
alkyne ---> (vinyl alcohol <--> ketone), markovnikov HgSO4, H2SO4
alkyne ---> (vinyl alcohol <--> aldehyde), anti-markovnikov 1)SiaBH*THF, 2) H2O2, NaOH
alkyne --> alpha-diketone KMnO4, H2O, Neutral
alkyne ---> carboxylic acids O3, H2O
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