Experiment #1

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Collin County Community College District *

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MISC

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Chemistry

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Feb 20, 2024

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docx

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3210. Experiment #1: Oxidation of Cyclohexanol to Cyclohexanone Objective: The objective of this experiment is to synthesize cyclohexanone and confirm the product by functional group analysis. Reaction equation: Materials: Instruments and glassware for distillation set up, thermometer, spatula, pH paper, starch iodide paper, boiling chips, glass stir rod, cyclohexanol, acetic acid, sodium hypochlorite, thymol blue, saturated sodium bisulfite solution, 6M NaOH solution, Ether, and NaCl. Reference table: Reagent MM MP Safety Hazard Structure Cyclohexanol 100.16 g/mol 25.93 C Irritant Acetic acid 60.05 g/mol 16.6 C Flammable, Corrosive
Sodium hypochlorite 74.44 g/mol 18 C Corrosive, Environmental hazard Thymol blue 466.6 g/mol 283-285 C Irritant Saturated bisulfite solution 104.6 g/mol 150 C Irritant NaOH solution 39.997 g/mol 318 C Corrosive NaCl 58.44 g/mol 801 C Irritant Ether 74.12 g/mol -116.3 C Flammable, Irritant Procedure: 1. Fill beaker half full of water and place on a hot plate. Check temperature for 45 C. 2. Measure 150mg of Cyclohexanol. Record the amount. 3. Measure 70-100mg of acetic acid into a 5mL long-necked round-bottom flask. 4. Measure 2mL of 6% sodium hypochlorite solution then add the total volume to the 5mL long-necked round-bottom flask. Gently swirl contents of the flask for three minutes. Note any observations with temperature.
5. Check the pH of the mixture using the iodide paper. Test for presence of hypochlorite using the starch iodide paper. If the iodide paper gives a negative test, add two drops of sodium bisulfite to the reaction. Test again. Add more sodium bisulfite if needed. 6. If first result was negative, add more hypochlorite solution. Place on hotplate and test again. Redo starch iodide test for a negative result. 7. Add a few drops of thymol blue, then add 6M of NaOH to the long-necked round-bottom flask. Record observations. 8. Set up distillation apparatus. Cool the solution to rt after. 9. Add 2 drops of solution into 2,4-DNP. Record Observations. 10. Salt out by adding NaCl to reaction mixture. 11. Extract using 2-3mL of ether. Perform at least 2 times. 12. Evaporate organic layer by heating. Use wooden sticks to prevent bumping. Data/Observations: Measurement Starting amount of cyclohexanol .15g Starting mount of azelaic acid .68g Amount of sodium chloride added to cyclohexanone and water distillate .102g Mask of pre-weighed flask 16.9g Mask of flask with organic layer 17.45g Acidic solution felt warm/hot after sodium hypochlorite was added. After solution was heated, it tested negative for hypochlorite. Tested positive for hypochlorite when flask was cooled.
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Inorganic layer was cloudy/ blurry, organic layer appeared clear. Percent yield: (17.45-16.9)/ .15= 3.66 3.66x100= 366% **percent yield indicates an error must have taken place during the experiment. Conclusion: In this experiment, cyclohexanone was synthesized from cyclohexanol. Cyclohexanol was oxidized with hypochlorite as the oxidizing agent. However, the experiment was not completely successful. A percent yield of 366% indicates some sort of error has occurred during the experiment. The starting amount of cyclohexanol was .15 grams, so it is impossible to have more than what was started with. It is possible that there may have been some brine solution in the flask when the final mask was calculated. Also, there were also some issues with the distillation setup. Too many boiling chips were added which causes the solution to boil rapidly, the cyclohexanone solution could have evaporated too quickly. Future suggestions include carefully extracting the brine solution and not using too many boiling chips. Prelab questions: 1. Is there any significance for making cyclohexanone in the industry? Cyclohexanone is a good solvent for organic phosphorous pesticides. 2. Explain the reasons for the selection of NaOCl for the oxidation reactions vs chromium based oxidizing reagent in the labs? What is the role of acetic acid in this lab? Chromium reagents are hazardous and difficult to use in labs and dispose, however the salt that forms during the hypochlorite reaction makes disposing easier. The role of acetic acid is to react with NaOCl to form HOCl which oxidizes OH to a ketone. Post-lab questions:
1. What are the techniques that you learned in 3210 labs are applied here in this experiment? Explain your rationale for the selection. Techniques learned in 3210 labs that were applied in this experiment include distillation. Distillation works by evaporating a solution once its boiling point is reached. Extraction was also performed in 3210 labs and in this experiment. Performing extraction allows us to separate the organic layer from the inorganic layer. 2. What is the significance of pH adjustment in this experiment? pH adjustment is important because an acidic solution is required. The acid acts as a catalyst in the reaction turning NaOCl into HOCl.
References: National Center for Biotechnology Information. "PubChem Compound Summary for CID 3283, Ether"  PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Ether . Accessed 31 January, 2022. National Center for Biotechnology Information. "PubChem Compound Summary for CID 7966, Cyclohexanol"  PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Cyclohexanol . Accessed 31 January, 2022. National Center for Biotechnology Information. "PubChem Compound Summary for CID 176, Acetic acid"  PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Acetic-acid . Accessed 31 January, 2022. National Center for Biotechnology Information. "PubChem Compound Summary for CID 23665760, Sodium hypochlorite"  PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Sodium-hypochlorite . Accessed 31 January, 2022. National Center for Biotechnology Information. "PubChem Compound Summary for CID 65565, Thymol blue"  PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Thymol-blue . Accessed 31 January, 2022. National Center for Biotechnology Information. "PubChem Compound Summary for CID 23665763, Sodium bisulfite"  PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Sodium- bisulfite . Accessed 1 February, 2022. National Center for Biotechnology Information. "PubChem Compound Summary for CID 14798, Sodium hydroxide"  PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Sodium- hydroxide . Accessed 1 February, 2022. National Center for Biotechnology Information. "PubChem Compound Summary for CID 5234, Sodium chloride"  PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Sodium-chloride . Accessed 1 February, 2022.
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