SC CHEM 333 - Oxidation of Cyclohexanol to Cyclohexanone Post-Lab (4 pages)

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Oxidation of Cyclohexanol to Cyclohexanone Post-Lab



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Organic Chemistry 333L section 03M Laboratory Post Lab Oxidation of Cyclohexanol to Cyclohexanone By Cameron Kahn 22 October 2013 TA James Collie 1 Page Observations 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 melting point 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 x100 Melting Point Percent Difference 162oC 184oC x100 22 absolute value was taken nonnegative because Mass of product cyclohexanone conversion call it a 1 m ole of a 1 mof product call it b molar mass g of a molar mass g of b 1 mole of a starting mass mass of product cyclohe 1 mole of b Mass of product cyclohexanone conversion Cyclohexanol 1 mcyclohexanol 1 mCyclohexanone 100 16 g Cyclohexanol 98 14 g Cyclohexanone 1 mCyclohexanonol 0 17 g 0 16 g Cyclohexanone 1 mCyclohexanone2 P a g e Conclusions 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 solution until 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 point alone Carson This is proven to be true when the melting point at the end of the experiment was recorded 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 IR graph The O H stretch represents an alcohol phenyl stretch There is also a Carboxylic acid at 2400cm 1 Carboxylic Acids 3 Page Sp3 C H stretch O H stretch Carbonyl group References 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 Ta 4 Page


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