ch17-overview

ch17-overview - O H R C O OH R C O R R H C OH R dehydration...

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An overview of alcohol preparations: OH H H OH OH H HO OH OH HO R C O H RH 2 C OH R C O OR' RH 2 C OH R C O R' H C OH R' R R C O OH RH 2 C OH H C O H R' C O H R' C O R' H C OH R H R' C OH R H R' C OH R R' R' C O OR' R' C OH R R H + /H 2 O carbocation rearrangements 1. BH 3 , THF 1. Hg(OAc) 2 , H 2 O 1. OsO 4 2. H 2 O 2 , OH - anti -Markovnikov regiochemistry syn -addition 2. NaBH 4 Markovnikov regiochemistry ant i-addition 2. NaHSO 3 , H 2 O syn addition 1. MCPBA 2. H 3 O + ant i-addition 1. NaBH 4 or LiAlH 4 2. H 3 O + 1. LiAlH 4 2. H 3 O + 1. NaBH 4 or LiAlH 4 2. H 3 O + 1. LiAlH 4 2. H 3 O + 1. R MgX, ether 2. H 3 O + 1. R MgX, ether 2. H 3 O + 1. R MgX, ether 2. H 3 O + 2. H 3 O + 1. 2 R MgX, ether
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An overview of Alcohol Reactions: R' C OH R" H 2 C HX C R X R' R" C C R' H H H 3 O + R' C OH R" R R H C OH R' PBr 3 R H C Br R' SOCl 2 /pyridine R H C Cl R' SO 2 Cl H 3 C R H C OTos R' R" RH 2 C OH R C
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Unformatted text preview: O H R C O OH R C O R' R H C OH R' dehydration of 3 o alcohols 3 o alcohols only carbocation mechanism POCl 3 , pyridine dehydration of 2 o and 3 o alcohols only S N 2 mechanism inversion of configuration CrO 3 , H 2 SO 4 or CrO 3 , H 2 SO 4 1 o 2 o 2 o S N 2 mechanism inversion of configuration 3 o PCC / CH 2 Cl 2 PCC/ CH 2 Cl 2 Dehydration to yield alkenes Conversion into alkyl halides Oxidation conversion into tosylates H C C R' H H R"...
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ch17-overview - O H R C O OH R C O R R H C OH R dehydration...

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