Question

1 - Provide a balanced equation for this reaction

2 - Provide a mechanism for the transformation of cyclohexanol into cyclohexanone

3 - Provide a flow chart for the workup procedure for isolating cyclohexane from all the by-products, making sure to note in which layer you expect to find your product in each extraction.

4 - Provide the theoretical yield of cyclohexane in this experiment.

PROCEDURE OXIDATION OF CYCLOHEXANOL TO CYCLOHEXANONE Set up a water bath as the heat source to warm the reaction mixture on a stirrer/ hotplate. Use a 125-mL beaker for the water bath and place it directly on the surface of the hotplate (no need for a sandbath). The oxidant is significantly unstable above 50 °C, so careful temperature control is necessary 1. To your 5-mL long-necked round-bottomed flask, add 0.150 g of cyclohexa- nol, 0.3 mL of glacial (!!) acetic acid (CH,COOH), and 1.0 mL of acetone. 2. Add a magnetic stir bar. 3. Using the black Viton connector, attach an air condenser to the flask and clamp the assembly to a laboratory stand. Wrap the air condenser with a moist paper towel. 4. Immerse the flask in a water bath heated to 45 °C. (Do not go significantly above this temperature.) Start the stirplate at a medium setting. 5. Over the course of 30 minutes add a total of 6 mL of sodium hypochlorite solution (6% aqueous NaOCI, Ultra Clorox®) while maintaining stirring and heating for 30 minutes. Addition of 1 mL every 5 minutes is a good pace. (More frequent addition of smaller volumes is better than less frequent addi- tion of larger volumes.) 6. After the last addition continue stirring for 15 minutes. 7. Quench excess oxidant by the dropwise addition of saturated aqueous sodium bisulfite-test with starch-iodide paper and add more sodium bi- sulfite until the starch iodide paper no longer changes color (white → blue). (Test your starch iodide paper with bleach first so that you know what kind of color change you are looking for.) 10 ORGANIC CHEMISTRY 272L

Answer 1

HO H +Nacd t H20 Naou Mech! ноз + ci yplohxanons