orgo 2 lab 2 - Megan Gueli Lab Report 2 Chemistry 216...

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Megan Gueli Lab Report 2 Chemistry 216 February 15, 2012 Oxidation of a Secondary Alcohol with NaOCl Introduction: Oxidation in organic chemistry is defined as either loss of hydrogen atoms or the addition of bonds to oxygen or other atoms more electronegative than carbon. Oxidation of alcohols provides a general method for the preparation of carbonyl compounds. Oxidation of secondary alcohols produces ketones, while oxidation of primary alcohols produce aldehydes or carboxylic acids. In the past chromium (VI) based reagents, such as Collins reagent, PDC, or PCC, were used for this purpose. However, most of these metal- based reagents are now known to be very toxic and carcinogenic. Therefore, nonmetal- based oxidants, such as bleach, were developed. There are many advantages to using NaOCl. It is cheap, oxidizes secondary alcohols rapidly and in high yield, and does not pose the problem of disposing of toxic metal wastes. To complete this experiment a steam distillation, extraction, and several washes will be performed in order to get a pure substance completely rid of water. Then characterization techniques such as thin-layer chromatography, melting points, and infrared spectrum will be used to characterize the final pure substance.
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Simple Reaction Scheme: Experimental: In a 10 mL round bottomed glass, 400 mg of cyclohexanol was added to 1.5 mol equivalent of acetic acid. Then as the solution was swirled, .75M aqueous sodium hypochlorite was added, while the acidic pH was maintained. The reaction temperature
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rose to about 45 degrees Celsius, and then as the temperature dropped the reaction flask was kept in a sand bath for an hour as the reaction was completed.
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This note was uploaded on 03/15/2012 for the course CHEM 216 taught by Professor Nolta during the Winter '07 term at University of Michigan.

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orgo 2 lab 2 - Megan Gueli Lab Report 2 Chemistry 216...

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