chem lab 5 - Hoang 1 Phuong Hoang Chem 3105 541 10/08/08...

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Hoang 1 Phuong Hoang Chem 3105 – 541 10/08/08 Experiment 5: Oxidation of Alcohols; Trends in Infrared Spectroscopy I. Purpose: The purpose of this experiment is to prepare an aldehyde or ketone by oxidation of the corresponding 1 o and 2 o alcohols and obtain the infrared spectra of the compounds. II. Background: Oxidation means the removal of electrons. The initial oxidation step followed by the loss of a proton gives a radical. The loss of a proton from carbon is favored because the radical is resonance stabilized. The radical can be easily oxidized again; loss of another proton gives the corresponding carbonyl compound. In this experiment, TEMPO is used as a catalytic oxidant and TCCA is used as the stoichiometric oxidant. TEMPO is reduced to hydroxylamine. TCCA does not react directly with alcohols but will reoxidize the hydroxylamine to the TEMPO cation. Oxidation of a primary alcohol to an aldehyde is a particularly challenging reaction because it can be overoxidized to a carboxylic acid. In the presence of water, aldehydes exist in
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chem lab 5 - Hoang 1 Phuong Hoang Chem 3105 541 10/08/08...

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