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Reduction of a Ketone: Preparation of Fluorenol from Fluorenone This semester we have focused on the reactions of carbonyl containing compounds. The reduction of the carbonyl group using sodium borohydride can be used to functionalize ketones and aldehydes to the corresponding alcohol. Goals Prepare fluorenol, monitor the reaction by TLC, purify the product, and analyze the product using infrared spectroscopy and melting point determination. Reaction scheme: NaBH CH OH Read chapter on TLC to refresh your memory (pp Organic Chemistry) 253-267 in 'Laboratory Techniques in References 1. Wilson, B. College of Lake County, Organic Chemistry 223, Spring 2016 2. Procedure adapted from Pavia, D.L et al, Introduction to Laboratory Techniques 4 Ed. Thomson Brooks/Cole: Mason, OH, 2006; pp. 46-50 Procedure: 1. Weigh out 0.400 g of fluorenone, place it in 10 mL round bottom flask and add a spin vane (stir-bar). No heat!! 2. Add 8 mL of methanol to the flask and stir the solution until the fluorenone is dissolved. 3. While the fluorenone is dissolving set-up the TLC. 4. Get a TLC chamber and add dichloromethane (eluent). 5. Get a TLC plate (or cut) and capillary tube (both ends open) for spotting the plate also get a small Erlenmeyer flask with acetone for your capillary tube (rinse in between spottings) 5 6. The plate should look as diagrammed below. When spotting leave room in either edge to Width: 2 by ¾ inches prevent smiling Length: 3 inches this side up TLC plate 0 15 30 45 60 75
