Oxidation of Cyclohexanone to Adipic Acid Essay

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Pages: 4
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April Goodson
CHEM 242L-002
February 20, 2013

Oxidation of Cyclohexanone to Adipic Acid
Abstract
The cyclic ketone cyclohexanone was oxidized to adipic acid using the oxidizing agent nitric acid. The experiment yielded 0.2667 grams of adipic acid, giving a percent yield of 113.97%. Although the product was allowed to dry for one week, residual moisture was still present in the sample and a melting point could not be obtained. This error in the experiment either resulted from adding too much water or not allowing the product to remain in the Hirsch vacuum filtration for long enough to sufficiently dry.
Introduction
Redox reactions are an important class of reactions in organic chemistry that involve the transfer of electrons from …show more content…
After the last drop of cyclohexanone was added, the reaction tube was placed back into the sand bath and boiled for one minute. The tube was then removed from the sand bath and allowed to cool to room temperature before being placed in an ice bath for three minute. Three drops of water were added to the reaction tube while it remained in the ice bath. The product was collected by Hirsch vacuum filtration and allowed to dry for the period of one week before weight and melting point were obtained.
Results
The experiment yielded 0.2667 grams of adipic acid, giving a percent yield of 113.97% yield. The product contained residual moisture and was not in a solid state, so that a melting point could not be obtained.

Discussion
The adipic acid produced by this experiment still contained moisture and was not in a solid state after one week, giving a large degree of inaccuracy in the percent yield and not allowing for a melting point to be taking. This is somewhat limiting, in that a comment on the purity of the product cannot be given without a melting point. The product was likely too wet because it was not allowed to dry long enough in the Hirsch vacuum filtration process. Adipic acid is also very soluble in water, so that adding too much water while the product was one the ice bath may have dissolved some of the crystals (Gaivoronskii & Granzhan, 2005). The degree to which the adipic acid is soluble in water has also
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