216+W11-Expt+2 - Chem 216 W11 Notes Topic: _Experiment 2_...

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Chem 216 W11 Notes Topic : _Experiment 2_ page 1 of 3. Experiment 2. Oxidation of an Alcohol (see Ege’s: pp 515-519) C R R' H O-H [ox] C O R R' R = alkyl or aryl; R' = H 1 o -alcohol: R/R' = alkyl or aryl 2 o -alcohol: C O R H aldehyde C O R R' ketone • A number of chromium (VI)-based reagents have been developed for the oxidation of alcohols, e.g., Jones’ reagent [CrO 3 /H 2 SO 4 /acetone/water]. The oxidation of a primary alcohol by the use of the Jones’ reagent results in the formation of mostly a carboxylic acid. • Pyridinium chlorochromate (abbreviated as PCC; developed in 1975 by E. J. Corey) is one of the mildest and yet highly versatile reagents used for the oxidation of alcohols. With this reagent, the oxidation of a primary alcohol cleanly produces the corresponding aldehyde. Mechanism of the PCC oxidation of an alcohol: C R R' H O-H Cr O O O Cl more electrophilic than the Cr in CrO 3 because of Cl C R R' O H Cr O O O H Cl N H N H C R R' O H Cr O H N H O O -Cl Cl still Cr +6 B: extremely acidic! C R R' O Cr O H N H O O Cl still Cr +6 often referred to as "Chromate" ester oxidation step B: C O R R' Cr O O O + Cr
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This note was uploaded on 04/24/2011 for the course CHEMISTRY 216 taught by Professor Schultz during the Winter '11 term at University of Michigan.

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216+W11-Expt+2 - Chem 216 W11 Notes Topic: _Experiment 2_...

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