CHML212 Exp. 19 Oxidation of 9-Fluorenol IN-LAB ASSIGNMENT: (EACH STUDENT will record the following data in his/her laboratory notebook in a well organized manner during lab period. Yellow carbon copies will be submitted for grading along with Post-Lab assignment.) …..max score = 20 pts. 6. Data/Calculations a. b. c. d. e. f. g. h. i. j. k. Initial mass of 9-fluorenol used TLC diagram (s) with all cm measurements Initial mass of 150 mL beaker Final mass of 150 mL beaker + product Final product mass Physical state and color of product Theoretical yield calculation Percent yield calculation Atom economy calculation Cost per synthesis and cost per gram calculations All TLC Rf value calculations 7. In-lab Question (The following question should be answered in laboratory notebook.) a. Using the mechanism proposed in this experiment, draw the product, and a complete mechanism for its formation, for the following reaction: OH HOCl Cl H3O+ + O H H ? CHML212 Exp. 19 Oxidation of 9-Fluorenol POST-LAB ASSIGNMENT: (EACH LAB GROUP will submit one copy of a typewritten, paragraph style report addressing all of the points listed below. Must be written using PAST TENSE, PASSIVE VOICE. ) …..max score = 50 pts. 8. Experimental (Write 1-2 paragraphs including all of the following. Do NOT present a bulleted outline.) What type of reaction did you perform? Describe the actual synthetic procedure. Include names of any reactants used and desired product, as well as name of solvent and catalyst used (if any). Be sure to give actual volumes/masses of compounds used during the synthesis (not just what the lab manual tells you to use). Describe the purification technique used to isolate the desired product, including names and actual volume/mass of any compounds used during purification. Describe the analytical technique used to evaluate the product, including names and actual volume/mass of any compounds used during sample prep, and any type of spectral analysis used. 9. Results (Complete, then copy/paste completed tables into your document.) Table 19.1 Experimental results Theoretical Yield (g) Actual Yield (g) Percent Yield Melting Range (oC) Product Appearance Table 19.2 Green chemistry results Table 19.3 Final TLC analysis Atom Economy (%) Cost per Synthesis ($) Cost per Gram ($/g) Compound TLC Rf values Standards Sample 9-fluorenone 9-fluorenol Table 19.4 IR analysis Functional Group O-H stretch C-O stretch C=O stretch sp2 CH stretch Base Values (cm-1) 3200–3400 1000–1200 1705–1725 3000–3100 9-fluorenol 9-fluorenone 10. Discussion (Write 1-2 pages addressing all of the following points.) Based on the TLC results, were the reactants completely converted to the desired product? Explain this conclusion by giving the identity and Rf values of all provided standards and any compounds detected in the sample during TLC analysis. How can IR spectroscopy be used to differentiate between the reactant and the product in this experiment? Give the identity of one type of absorption and explain how it could be used to determine whether or not the conversion took place. Include the typical frequency and the actual frequency for this type of bond in your statement. Include a short comment addressing what could be done differently to improve the experimental results, if repeated.