Organic Chemistry 333L, section 03M LaboratoryPre-LabOxidation of Cyclohexanol to CyclohexanoneBy: Cameron Kahn8 October 2013TA: James Collie1 | P a g eObjectives:In this experiment, one will oxidize cyclohexanol to cyclohexanone using hypochlorite oxidation(Ali). The experiment will also isolate and determine the percent yield of cyclohexanone. Lastly, he/she will make a derivative of the product with 2,4-dinitrophenylhydrazine (2,4-DNP) and determine its melting point (Ali).Theory:Oxidation is the loss of electrons by such species as atoms, molecules, or ions (Ali). Oxidation is defined as an increase in C-O bonds and a decrease in C-H bonds. Reduction is the gain of elections by such species as atoms, molecules, or ions. Reduction happens when there is a decrease in C-O bonds and/or increase in C-H bonds[ CITATION Geo122 \l 1033 ]. An oxidation agent stimulates oxidation and is a substance that takes elections in a chemical reaction. When an oxidation agent oxidizes something, it is reduced in the process. Some common oxidizing agents are sodium hypochlorite (common house hold bleach), Nitric acid (HNO3), and Sodium dichromate (Na2Cr2O7). Some common oxidations that occur are the browning of apples or the rusting of metals.The compound derived from a similar compound by some chemical process is called its derivative. The purpose for making a derivative of a ketone is for the identification of the presence or absence of a carbonyl group (C=O). Most ketones present themselves as liquids and a melting point cannot be obtained to determine its identity[ CITATION Geo122 \l 1033 ]. With the addition of 2,4-DNP, aldehydes and ketones react with 2,4 DNP reagent to form yellow, orange, or reddish-orange precipitates, whereas alcohols do not react. The formation of a precipitate therefore indicates the presence of an aldehyde or ketone. The precipitate from this test also serves as a solid derivative[ CITATION Dep12 \l 1033 ].A reason to add sodium bisulfite to the solution is that it consumes excess oxidizing agents (hypochlorite) by means of destroying the chlorine that is generated as a by-product. Sodium hydroxide is used to neutralize the acidic solution whereas sodium chloride is used to extract the cyclohexanone.The need for green chemistry is one of the ways we will be able to save human kind for the toxicity of our own advancements in chemistry. “Green chemistry also known as sustainable chemistry is the design of chemical products and processes that reduce or eliminate the use or generation of hazardous substances. Green chemistry applies across the life cycle of chemical products, including is design, manufacture, and use.” (www.epa.gov)[ CITATION Geo122 \l 1033 ].2 | P a g eMechanism:3 | P a g eProcedure:Start by weighing a small test tube and recording its weight. Add .17mL of cyclohexanol into a small test tube with .1mL of acetic acid and 2.3mL of NaOCl. Cover the test tube with a stopper and agitate for three minutes, being sure to ventilate frequently. Next, removed the stopper and place the test tube in a warm water bath at approximately 45°C and let sit for 15 minutes. Add three drops of sodium bisulfite with .4mL of 6M NaOH and stir solution. Next, add .15g of NaCl to the solution and cover with a stopper then agitate until the salt has dissolved. Add .4mL of Ether which is about 16 drops. Collect and keep the top layer and add this to a test tube which mass has already been recorded. Repeat steps 8 and 9, placing more of the top layer into the same tube. Evaporate the ether off the top of the collected solution using a steam bath. Obtain the mass and calculate the percent yield of thecollected liquid product. Side note: make sure to set aside some product for the IR analysis. Prepare the 2,4-DNP derivative (cyclohexanone) by adding one drop of 2,4-DNP for every .01 grams of cyclohexanone being converted in a small test tube. Gently heat the mixture for one minute and collect the dry derivative using suction filtration. Determine the melting point of the derivative and then compare that number to the actual melting point. Apparatus:Reagent Table:4 | P a g eFigure 1 Figure 2Both are from the Lab manual (Ali)Name StructureMolecular Weight (g/mol)Melting Point (oC)Boiling Point (oC)Density (g/mL)Acetic AcidCH3COOH60.05 16.2 117-118 1.049Sodium ChlorideNaCl 58.44 801 1413 2.165Sodium BisulfiteNaHSO3104.05 150 dec - 1.48Sodium HypochloriteNaOCl74.44 -6 40 1.206Sodium HydroxideNaOH 39.997 318 1390 2.132,4-DNPC6H6N4O4198.13 198 - -CyclohexanolC6H11OH100.16 20-22 161 0.948Diethyl EtherC4H10O74.12 -116.3 34.6 0.7134CyclohexanoneC6H10O98.14 -47 155 0.9475 | P a g eDisposal:The disposal and safety of 2,4-DNP needs extra attention when handling the solution which is 85% phosphoric acid and will stain things permanently. Any aqueous solutions left need to be washed down the drains with ample amount of water. Dispose of all 2,4-DNP filtrate liquids and other organic solvents in the organic liquid waste container which is located under the fume hood. Aldehyde and ketone derivatives should be disposed of in the solid waste container locatedunder the fume hood. Dispose of soiled gloves in the glove bucket and paper towels need to be placed in the general waste basket. Broken glass always goes in the broken glass container and if unsure about any disposal consults the TA.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>2.6 | P a g