Chapter 17 - 17.6 Alcohols to Alkyl Halides Tertiary react...

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Sheet1 Page 1 Chapter 17 17.2 Formation of alkoxide ions Alkali metals and strong bases (NaH, NaNH2, and grignard reagents) 17.3 Hydroboration/Oxidation: yields syn, non-markovnikov product Oxymercuration/Reduction: yields markovnikov product 1,2-Diols prepared by: 1. OsO4/2. NaHSO3 acid catalyzed hydrolysis of an epoxide (epoxide formed by alkene reacted with RCO3H) 17.4 Reduction using NaBH4 or LiAlH4 17.5 Grignard: reduces C=O to C-OH and adds on R group from reagent Esters: reduces C=O and cleaves C-OR, attaches two groups from reagent to central C atom
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Unformatted text preview: 17.6 Alcohols to Alkyl Halides: Tertiary: react with HCl or HBr (by SN1) Primary/Secondary: SOCl2, PBr3 (by SN2) Dehydration: Tertiary: acid catalyzed dehydration (H2SO4) (by E1) Secondary or Tertiary: POCl3/pyridine (base) (by E2) 17.7 Oxidation: Primary: PCC-->aldehyde, CrO3 (Jones Reagent)--> carboxylic acid Secondary: PCC-->ketone can also use any Cr3O7 Sheet1 Page 2 17.8 TMS-Cl is a protecting group, removed by either acid or fluoride ion (LiF)...
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