Exam 1 Notes - Chapter 13 I II III Oxidation of alcohols...

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1°-OH aldehyde carboxylic acid 2°-OH ketone 3°-OH no reaction neral mechanism for oxidation of alcohols C-OH -------> --------> ke a good LG se elmination Step 1: protonation Step 2: Addition of nucleophile Formaldehyde to 3 ° -OH Rioprostil Chapter 13 I. Oxidation of alcohols II. Oxygen atoms as nucleophiles III. Oxygen atoms as leaving groups I. Oxidation of alcohols: to lose electrons A. Nomenclature Oxidation Numbers C-C = 0 C-H = +1 C=O = -2 C-X = -1 1. C-OH = -1 B. Reagents used to oxidize alcohols 1. Chromium Reagents (Cr +6 Cr +3 ) (a) Acidic, aqueous solutions (1) Jones reagent: CrO 3 /H 2 SO 4 (2) Chromate: Na 2 CrO 4 /H 2 SO 4 (3) Dichromate: Na 2 Cr 2 O 7 /H 2 SO 4
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(4) Chromic Acid: H 2 CrO 4 (b) Basic, anhydrous solutions (Stops at the aldehyde) (1) Chromium trioxide: CrO 3 + pyridine (2) PCC = Pyridinium chlorochromate: CrO 3 Cl - pyridine + -H (3) PDC = Pyridinium dichromate: Cr 2 O 7 [pyr-H] 2 +2 C. Oxidation of 1 ° Alcohols 1. Using Chromium compounds
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Formation of Hydrate ** Why don’t tertiary alcohols get oxidized?
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