SC CHEM 333 - Oxidation of Cyclohexanol to Cyclohexanone Pre-Lab (6 pages)

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Oxidation of Cyclohexanol to Cyclohexanone Pre-Lab



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Organic Chemistry 333L section 03M Laboratory Pre Lab Oxidation of Cyclohexanol to Cyclohexanone By Cameron Kahn 8 October 2013 TA James Collie 1 Page Objectives 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 Page Mechanism 3 Page Procedure 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 the collected 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 Figure 1 Figure 2 Both are from the Lab manual Ali Reagent Table 4 Page Name Structure Melting Molecular Point Weight g mol o C Boiling Point oC Density g mL 60 05 16 2 117 118 1 049 58 44 801 1413 2 165 104 05 150 dec 1 48 74 44 6 40 1 206 39 997 318 1390 2 13 198 13 198 100 16 20 22 161 0 948 74 12 116 3 34 6 0 7134 98 14 47 155 0 947 CH3COOH Acetic Acid Sodium Chloride NaCl NaHSO3 Sodium Bisulfite Sodium Hypochlorite Sodium Hydroxide NaOCl NaOH C6H6N4O4 2 4 DNP C6H11OH Cyclohexanol C4H10O Diethyl Ether C6H10O Cyclohexanone 5 Page Disposal 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 located under 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 Page


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