Lect26_1026 - retention of configuration Ch. 8 - 11 10....

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Ch. 8 - 1 6. Alcohols from Alkenes through Oxymercuration–Demercuration: Markovnikov Addition Step 1: Oxymercuration Step 2: Demercuration 4
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Ch. 8 - 2 H 2 O Comparison acid-catalyzed hydration Methanide migration 2 4
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Ch. 8 - 3 Solvomercuration-Demercuration 2 3 4 2 3 2
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Ch. 8 - 4 syn addition Anti-Markovnikov addition 7. Alcohols from Alkenes through Hydroboration–Oxidation: Anti-Markovnikov Syn Hydration
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Ch. 8 - 5 antiaddition Markovnikov addition Compare with oxymercuration- demercuration
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Ch. 8 - 6 Stereochemistry H 2 O 3 3 4 Not Stereoselective
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Ch. 8 - 7 Other examples (1) H B H 2 -THF H B H 2 H 2 B H + (99 : 1) (2) H B H 2 -THF H B H 2 H 2 B H + (98 : 2)
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Ch. 8 - 8 9. Oxidation and Hydrolysis of Alkylboranes B always ends up on the least hindered carbon
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Ch. 8 - 9 Oxidation NaOH H 2 O O B O O OH +N a 3 BO 3 3
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Ch. 8 - 10 Overall synthetic process of hydroboration- oxidation-hydrolysis Overall: anti-Markovnikov addition of H– OH across a C=C bond Opposite regioisomers as oxymercuration-demercuration This oxidation step occurs with
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Unformatted text preview: retention of configuration Ch. 8 - 11 10. Summary of Alkene Hydration Methods Summary of Methods for Converting Alkene to Alcohol Reaction Regiochemistry Stereochemistry Occurrence of Rearrangements Acid-catalyzed hydration Markovnikov addition Not controlled Frequent Oxymercuration-demercuration Markovnikov addition Not controlled Seldom Hydroboration-oxidation Anti-Markovnikov addition Stereospecific: synaddition of H and OH Seldom Ch. 8 - 12 Examples 1. Hg(OAc) 2 , THF-H 2 O 2. NaBH 4 , OH H OH 1. B H 3-THF 2. H 2 O 2 , OH OH H with rearrangement Markovnikov addition of H 2 O without rearrangement anti-Markovni-kov, syn addition of H 2 O Ch. 8 - 13 11. Electrophilic Addition of Bromine and Chlorine to Alkenes Addition of XX (X = Cl, Br) across a C=C bond 2 4 Ch. 8 - 14 4 Stereochemistry Anti addition N...
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This note was uploaded on 02/20/2012 for the course CHEM 333 taught by Professor Lavigne during the Fall '09 term at South Carolina.

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Lect26_1026 - retention of configuration Ch. 8 - 11 10....

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