7-StereochemistryReactionsHLSF07

7-StereochemistryReactionsHLSF07 - Stereoselective Addition...

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Stereoselective Addition Reactions: A. Anti addition : X 2 , X 2 /H 2 O, Hg(OAc) 2 /H 2 O Br 2 Br Br Br Br I 2 H 2 O HO I HO I Hg(OAc) 2 H 2 O AcOHg OH H H 3 C H CH 3 Hg(OAc) 2 HO H CH 3 H H 3 C
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B. Syn Addition: H 2 /Pd, BH 3 D 2 D D Pd/C D D BD 3 D 2 B D D 2 B D
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Non-Stereoselective Addition Reactions: Both Syn and Anti addition : HX, H 3 O + , HBr/ROOR/ Δ DCl D Cl Cl D D Cl Cl D DBr ROOR Br ! D Br D Br D Br D D 3 O+ OD D OD D OD D OD D
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Substitution Reactions: Inversion Retention I I Syn Addition H 2 O H 2 O Inversion of Configuration OH OH I I Net Anti Addition I 2 BD 3 D 2 B D D 2 B D Syn Addition Retention of Configuration HO D HO D Net Syn Addition H 2 O 2 , NaOH H 2 O H 2 O 2 , NaOH H 2 O
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Substitution Reactions: Inversion and Retention Not always this interesting . AcOHg OH AcOHg OH NaBD 4 NaBD 4 Inversion and Retention D OH D OH D OH D OH Hg(OAc) 2 H 2 O Anti Addition Net Syn and Anti Addition AcOHg OH AcOHg OH NaB H 4 NaB H 4 Inversion and Retention H OH H OH H OH H OH Hg(OAc) 2 H 2 O Anti Addition
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This note was uploaded on 05/13/2010 for the course CHEM 151L taught by Professor Roy,christopher during the Fall '08 term at Duke.

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7-StereochemistryReactionsHLSF07 - Stereoselective Addition...

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