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SC CHEM 333 - Oxidation of Cyclohexanol to Cyclohexanone Post-Lab

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Organic Chemistry 333L, section 03M LaboratoryPost-LabOxidation of Cyclohexanol to CyclohexanoneBy: Cameron Kahn22 October 2013TA: James Collie1 | P a g eObservations:When the cyclohexanol was added to the small test tube, a clear liquid and a peppermint like odor was observed. With the addition of acetic acid, a clear liquid, and sodium bicarbonate, a white powder looking substance, to the cyclohexanol, the sodium bicarbonate dissolved into the solution. After the addition of sodium bisulfite and sodium hydroxide, the solution remained transparent. With the addition of ether, the solution decomposed into two separate layers. The bottom layer was a clear solution and the top layer a cloudy solution (Sciences). The top layer was the organic layer. The addition of 2, 4-DNP, a yellowish looking solution, to the organic layer, formed a yellow sand looking precipitate. Results:The theoretical melting point of 2, 4-DNP derivative was 162oC. The melting point observed in the lab experiment of 2, 4-DNP was 184oC, a 22% difference. The liquid was already at it meltingpoint at room temperature. With the addition of 2, 4-DNP a solid was formed, increasing the melting point. To calculate the theoretical yield of a reaction, first determine and calculate the limiting reagent. Since the amounts of the starting materials are given, calculate which reagents are in excess and which are limiting. For this experiment it is quite simple since cyclohexanol is the only reagent which is changed; therefore it is the limiting reagents for this experiment[ CITATION Geo122 \l 1033 ]. The starting amount of cyclohexanol was 0.17g and the mass of the final product of cyclohexanone was 0.15g. The theoretical yield of cyclohexanone was 0.16g and the mass of the final product falls below this number making the final product recovered, acceptable. The percentage yield of cyclohexanone was 0.88%. Calculations:Melting Point Percent Difference= [Theoretical temperature (oC)-Actual Temperature (oC)]x100Melting Point Percent Difference= [162oC-184oC]x100=22% nonnegative because absolute value was takenMass of product (cyclohexanone)-conversionstarting mass(call it a )∗1 m ole of amolar mass(g)of a∗1 mof product (call it b)1 mole of a∗molar mass(g)of b1 mole of b=mass of product (cyclohexanone)Mass of product (cyclohexanone)-conversion2 | P a g e0.17 gCyclohexanol∗1 mcyclohexanol100.16 g Cyclohexanol∗1 mCyclohexanone1 mCyclohexanonol∗98.14 g Cyclohexanone1mCyclohexanone=0.16 g CyclohexanoneConclusions:The experiment consisted of mixing cyclohexanol, acetic acid, and NaOCL in a small test tube and heating for 15 minutes. Next sodium bisulfite, NaOH, and NaCL was mixed into the solutionuntil most of the salt dissolved. With the addition of ether, the salt pushes the organic compound into the ether layer, separating the solution into two layers. This happens because the product was only slightly soluble in water; therefore the salt out process decreases the amount of “free” water to dissolve in (Carson). This forces the product into the either layer. With the layers separated, the top layer was placed into a small test tube and the bottom layer was washed down the drain responsibly. The solution that was retained was then divided into two parts or samples. One sample was used for IR analysis and the other had 2, 4-DNP added to it in order to form a precipitate. The precipitate that formed was then filtered and used to check the melting point. This lab experiment taught me that some liquids could be turned into a solid. Melting points of liquids cannot be measured however, when a liquid is turned into a solid then the melting point can be measured. It is important to note that if it is the same compound, the melting point does not raise. The use of 2,4-DNP derivative was to obtain a sharp melting point to use for identification. A 2,4-DNP derivative was needed because aldehydes and ketones all have a very small range of melting points, which makes it difficult to identify the compound by melting pointalone (Carson). This is proven to be true when the melting point at the end of the experiment wasrecorded to be 184˚C, a 1.14% higher value than the textbook value of 162oC. Analysis of IR/NMR:There is a peak at about1700 cm-1 which indicates a carbonyl carbon. Lack of peaks for other carbonyl groups suggests a ketone. There also exists sp3 carbon to hydrogen stretch within the IRgraph. The O-H stretch represents an alcohol/phenyl stretch. There is also a Carboxylic acid at 2400cm-1.3 | P a g eCarboxylic AcidsReferences:1. Ali, George Handy and Salman. Essentials of Organic Chemistry. Montgomery, Al: QDE Press, 2012.Sciences, Department of Chemistry in the College of Natural. " Department of Chemistry in the College of Natural Sciences." 01 01 2012. UMass Amherst. 02 23 2013 <http://www.chem.umass.edu/~samal/269/aak.pdf>2.3. Carson, James. Lab Ta4 | P a g eO-H stretchSp3 C-HstretchCarbonyl


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