Ch 10 everything

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20 Terms

1
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HX (HCl, HBr, HI) + alkene = ?
HYDROHALOGENATION. Adds H + X. Markovnikov. X goes to MORE substituted carbon. Both syn and anti possible. Carbocation = YES. Rearrangements = YES.
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Hydrohalogenation: does it have rearrangements?
YES. HX addition forms a carbocation, so carbocation rearrangements are possible.
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Hydrohalogenation: Markovnikov or anti-Markovnikov?
MARKOVNIKOV. H goes to LESS substituted carbon and X goes to MORE substituted carbon.
4
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Hydrohalogenation: syn or anti?
BOTH are possible. It is not specifically syn or anti because of the planar carbocation intermediate.
5
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H2O/H+ + alkene = ?
HYDRATION. Adds H + OH. Markovnikov. OH goes to MORE substituted carbon. Both syn and anti possible. Carbocation = YES. Rearrangements = YES.
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Hydration: does it have rearrangements?
YES. A carbocation intermediate forms, so rearrangements are possible.
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Hydration: where does OH go?
MORE substituted carbon. Markovnikov addition.
8
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Hydration: syn or anti?
BOTH are possible. It is not specifically syn or anti because of the carbocation pathway.
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Br2 or Cl2 + alkene = ?
HALOGENATION. Adds X + X. ANTI addition. Forms a halonium ion. No carbocation. NO rearrangements.
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Halogenation: does it have rearrangements?
NO. It forms a bridged halonium ion rather than a free carbocation.
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Halogenation: syn or anti?
ANTI.
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Halogenation: Markovnikov or anti-Markovnikov?
Neither. The same halogen is added to both alkene carbons.
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X2/H2O + alkene = ?
HALOHYDRIN FORMATION. Adds X + OH. OH goes to MORE substituted carbon. ANTI addition. Halonium ion intermediate. NO carbocation rearrangements.
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Halohydrin formation: where does OH go?
MORE substituted carbon. X goes to LESS substituted carbon.
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Halohydrin formation: syn or anti?
ANTI.
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Halohydrin formation: does it have rearrangements?
NO. It proceeds through a halonium ion rather than a free carbocation.
17
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1) BH3·THF 2) H2O2, OH− + alkene = ?
HYDROBORATION-OXIDATION. Adds H + OH. ANTI-Markovnikov. OH goes to LESS substituted carbon. SYN addition. No carbocation. NO rearrangements.
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Hydroboration-oxidation: where does OH go?
LESS substituted carbon. Anti-Markovnikov.
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Hydroboration-oxidation: syn or anti?
SYN.
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Hydroboration-oxidation: does it have rearrangements?
NO. No free carbocation intermediate forms.