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Cyclohexanol to Cyclohexanone

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Chapter 22- Oxidation Reaction: Cyclohexanol to Cyclohexanone
Carlos E. Gonzales
(William Bridges)
March 18, 2015
CHM 246, Sec L02B

Purpose
The oxidation of a secondary alcohol to a ketone is accomplished by many different oxidizing agents, including sodium dichromate, pyridinium chlorochromate, and sodium hypochlorite (household bleach). In this experiment, we use sodium hypochlorite because it is much safer from an environmental standpoint. The mechanism of the reaction is not clear. It is not a free radical reaction, the reaction is much faster in acid than in base, elemental chlorine is presumably the oxidant, and hypochlorous acid must be present. It may form an intermediate alkyl hypochlorite ester, which by an E2 elimination gives the ketone and chloride ion. The purpose of this experiment is to oxidize an alcohol to a ketone with household bleach. The product is isolated by steam distillation and is extracted into the distillate with ether that is dried in a column of drying agents. Removal of the ether leaves the product cychohexanone.

Theory
Cyclohexanone is used as a precursor for nylon. This makes it one of the largest mass produced chemicals in the industry. Billions of kilograms of cyclohexanone are produced each year for the making of nylon. The synthesis of cyclohexanone is simple. First, sodium hypochlorite and acetic acid are reacted to yield hypochlorous acid. Second, hypochlorous acid is added to cyclohexanol to synthesize cyclohexanone.
After cyclohexanone is synthesized, it must be separated out from by-products. In order for it to be separated out, sodium chloride is added to the mixture. The sodium chloride will salt out the cyclohexanone from the aqueous layer. Now the aqueous layer and the cyclohexanone must be separated. Dichloromethane is added to the mixture. Next, the cyclohexanone and dichloromethane are separated from the

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