Term
| __________-__________ is another method for converting alkenes to alcohols with __________ orientation. |
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Definition
1) Oxymercuration-demercuration
2) Markovnikov |
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Term
| __________-__________ works well with alkenes that do not easily undergo direct __________, and it takes place under milder conditions. |
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Definition
1) Oxymercuration-demercuration
2) Hydration |
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Term
| In oxymercuration-demercuration reactions, there is no __________ formed, so there is no opportunity for __________. |
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Definition
1) Carbocation
2) Rearrangement |
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Term
| The reagent for mercuration is __________ __________ Hg(OCOCH3)2 or Hg(OAc)2; it acts as an electrophile because the __________ __________ dissolves slightly to form a __________ charged mercury species. |
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Definition
1) Mercuric acetate
2) Mercuric acetate
3) Positively |
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Term
Logistics of oxymercuration-demercuration reactions:
__________ involves an electrophilic attack on the double bond by the __________ charged mercury species.
The product is a __________ ion, an organometallic cation containing a three-membered ring.
In the second step, __________ from the solvent attacks the mercurinium ion to give (after deprotonation) an organomercurial __________.
The final reaction is __________, to remove the mercury.
__________ __________ replaced the mercuric acetate fragment with a hydrogen atom. |
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Definition
1) Oxymercuration
2) Positively
3) Mercurinium
4) Water
5) Alcohol
6) Demercuration |
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Term
| In oxymercuration-demercuration reactions, __________ involves an electrophilic attack on the double bond by the positively charged mercury species, while __________ is a reaction performed by sodium borohydride to remove mercury. |
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Definition
1) Oxymercuraiton
2) Demercuraiton |
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Term
*Mechanism 8-5: Oxymercuration of an Alkene*
Step 1: Electrophilic attack forms a __________ ion.
Step 2: __________ opens the ring to give an organomercurial alcohol. __________ then replaces the mercuric fragment with hydrogen to give the __________. |
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Definition
1) Mercurinium
2) Water
3) Demercuration
4) Alcohol |
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Term
Analysis of Oxymercuration-demercuration reactions:
Oxymercuration-demercuration of an unsymmetrical alkene generally gives __________ orientation of addition.
The __________ ion has a considerable amount of __________ charge in both carbon atoms, but there is more charge on the (less/more) highly substituted carbon atom, where it is more stable.
Attack by __________ occurs on this electrophilic carbon, giving __________ orientation.
The electrophile, __________ __________, remains bonded to the (less/more) substituted end of the double bond; reduction of the organomercurial alcohol then gives the __________ alcohol. |
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Definition
1) Markovnikov
2) Mercurinium
3) Positive
4) More
5) Water
6) Markovnikov
7) Mercuric acetate
8) Less
9) Markovnikov |
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Term
| Oxymercuration-demercuration reliably adds __________ across the double bond of an alkene with __________ orientation and without __________. |
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Definition
1) Water
2) Markovnikov
3) Rearrangement |
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Term
| Of the methods seen for __________ hydration of alkenes, __________-__________ is most commonly used in the laboratory; it provides better yields than __________-__________ hydration and avoids the possibilities of rearrangements. |
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Definition
1) Markovnikov
2) Oxymercuration-demercuraiton
3) Acid-catalyzed |
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