CHEM 3332 1st Edition Lecture 5Outline of Last Lecture Reactions of Alcohols I. OxidationsA. Oxidation of 1 alcohols: B. Oxidation of 2 alcohols: C. Oxidation of 3 alcohols [ox] : 1. Chromic acid reagenta) Na2Cr2O7/H2SO4/H2Ob) CrO3/H2SO4/H2O/acetone/ 0 (Jones reagent) 2.Pyridinumchlorochromate / CH2CL2 (written as: PCC/CH2CL2 or CrO3 pyridine HCL/CH2CL2)II. Formation of the tosylate ester (converting the OH group to a better leaving group)III. Conversion of alcohols to alkyl halides – The BEST methodsA. Formation of 3 alcohols: use hydrohalic acids (HBR,HCL) B. Formation of 1 / 2 alkyl halides from 1 / 2 alcohols: 1. Bromides: use PBR32. Chloridesa) PCL3 or PCL5b) SOCL2 – NOTE: The mechanism given on Pg 463 occurs only in solvents like dioxane. The more typical mechanism is SN2 IV. Dehydration of alcohols to alkenes (first discussed in Ch.7)A. For 3 , 2 alcohols use H2SO4 (conc)/heat (Be careful!E1, so may rearrange) B. For 1 (and 3 , 2 that may rearrange) use POCL3/pyridine – E2, so no carbons NOTE: this reagent is given by Wade in a chapter problemV. Formation of EthersWilliamson Ether Synthesis (symm. Or unsymmetrical ethers)Outline of Current Lecture VI. Ester FormationA. Fischer Esterfication (intermolecular dehydration) – mechanism this semester!B. Nucelophillic acyl substitution of acid chlorideVII. Unique reactions of 1,2 diolsA. Periodic acid cleavage B. Pinacol – Pinacolone RearrangementSpectroscopy ReviewThese notes represent a detailed interpretation of the professor’s lecture. GradeBuddy is best used as a supplement to your own notes, not as a substitute.Current LectureVI. Ester FormationA. Fischer Esterfication (intermolecular dehydration) – mechanism this semester!B. Nucelophillic acyl substitution of acid chlorideVII. Unique reactions of 1,2 diolsA. Periodic acid cleavage B. Pinacol – Pinacolone RearrangementSpectroscopy
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