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