Chapter 22 Procedure #4 Oxidation of Cyclohexanol
1. Use 250 ml Beaker equipped with a magnetic stirrer and the 8 ml cyclohexanol
2. Set beaker on a stirring platform
3. Mix 4 ml of Glatial Acetic Acid with 115 ml of household bleach (NaClO)
4. Place the mixture in a 125 ml Separatory Funnel
5. Attach sep funnel on a ring stand directly above the beaker
6. Turn the stirring platform on so the magnetic stirrer rotates without splashing
7. Suspend a thermometer attached to the ring stand directly into the mixture in the beaker.
8. Add the acidified bleach from the sep funnel into the beaker at a rate of 2 drops per second which should take 20 minutes while stirring with the stirrer. Do not let the temperature to go above 50 degrees. Have an ice bath on standby in case it drifts above 50.
9. Allow the reaction mixture to stir for an additional 20 minutes.
10. Heat the reaction mixture to 50 degrees C using a hot plate
11. Add 1 gram portions of NaHSO3 in order to reduce any excess bleach. Test using Starch-Iodide paper until the paper ceases to turn dark blue. Add 1 gram then stir and test with paper. If a positive test is secured then repeat the procedure with an additional 1 gram portion until a negative test is secured.
12. Add 3 drops of Thymol Blue indicator solution.
13. Add 15-20 ml of 6M NaOH and check for a sky blue color of solution. If the solution is not blue (for example green) then add an additional 5 ml of the 6M NaOH.
14. Transfer the reaction mixture to a 250 ml Round Bottom Distilling Flask. Rinse the beaker with 5 ml of water and transfer rinse to flask.
15. Simple distill (steam distill) collecting 40 ml of co-distillate (water and cyclohexanone) into a graduated cylinder as a receptacle.
16. Add 8 grams of solid Sodium Chloride to the co-distillate and stir to dissolve.
17. Transfer the co-distillate to a 125 ml separatory funnel
18. Rinse the graduated cylinder that you collected the co-distillate in using 5 ml of Methyl t-Butyl Ether and transfer into the separatory funnel.
19. Add 10-15 ml more of the ether to the separatory funnel, shake, and allow to separate.
20. Draw off the bottom water layer and discard into the sink.
21. Add 10 ml of 3M NaOH to the separatory funnel, shake, and allow layers to separate.
22. Draw off the lower water layer and discard
23. Add 15 ml of saturated Sodium Chloride solution, shake, and let the layers separate.
24. Draw off lower water layer and discard
25. Transfer ether layer to a 50 ml Erlenmyer Flask through the top of the funnel.
26.Add Na2SO4 (anhydrous) to the flask so as to just cover the bottom.
27. Dry for 10 minutes.
28. Decant dryed ether extract into a pre-weighed 50 ml Erlenmyer Flask that has a wood stick.
29. Place the 50 ml flask in a preheated water bath located under a vent hood.
30. Allow the ether to boil off. When bubbling stops after boiling has begun then the boiling process is complete.
31. Dry flask off and weigh
32. Calculate the % yield
33. Take an IR and a GC.
34. Keep the product cyclohexanone for the next experiment (#6)
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Umm, how interesting !!