Ch_322a_11.06

Ch_322a_11.06 - Anti-addition in the Oxymercuration Step,...

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Stereochemistry of the Oxymercuration Reaction The oxymercuration reaction proceeds with overall anti-addition to the alkene, as observed in bromination (section 8.7): CH 3 Hg(OAc) 2 THF, H 2 O Hg OAc + CH 3 H mercurinium ion O-H H : : (-H + ) CH 3 H HO Hg-OAc anti product CH 3 H HO H NaBH 4 , HO - reductive cleavage stereochemical details lost
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Key Features of the Oxymercuration-Demercuration Procedure Overall Markovnikov Addition Product No Carbocation-type Rearrangements Good Yields
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Unformatted text preview: Anti-addition in the Oxymercuration Step, but Fuzzy Stereochemical Details in the Reduction Step Quiz 11.06 Provide the product of the following oxymercuration-demercuration procedure. (CH 3 ) 2 C=CH 2 (i) Hg(OAc) 2 , THF, H 2 O (ii) NaBH 4 , KOH Is the oxymercuration-demercuration procedure overall a Markovnikov or anti-Markovnikov addition? (CH 3 ) 2 CCH 3 OH Markovnikov addition...
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Ch_322a_11.06 - Anti-addition in the Oxymercuration Step,...

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