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Reduction of a Ketone Pre Lab Assignment: Complete the pre-lab cover page and develop a procedure.

Draw the mechanism of the reaction you will complete in lab. Use the proper arrow drawing convention to show all bond making and bond breaking steps in the reaction. Include all intermediates, including resonance structures. Learning Goals: Understand both the conceptual and technical sides of reducing a ketone using a metal hydride Understand the concept of oxidation states with respect to alcohols and ketones Application of thin layer chromatography to monitor reaction progress Introduction: The reduction of carbonyl compounds to alcohols using metal hydride reagents is a common reaction. Two of the most common metal hydride reducing agents are sodium borohydride (NaBH4) and lithium aluminum hydride (LiAlH4). Sodium borohydride is the less reactive, and more selective of the two compounds. It will readily reduce aldehydes and ketones to primary and secondary alcohols (respectively), reduce esters only under select conditions, and is unreactive towards carboxylic acids and amides. Lithium aluminum hydride is much more reactive and less selective. It readily reduces aldehydes, ketones, esters, and carboxylic acids to alcohols (1o, 2o, 1o, and 1o respectively) and it reduces amides to the corresponding amine. An approximate mechanism for metal hydride reduction is shown below. Reduction of a ketone:
MH3 O O H2O H OH

H H MH3

Reduction of an ester:
MH3 O O H O O H H H MH3 H MH3 O CH 3 O O H 2O H H H MH3 OH

In this lab you will use sodium borohydride to reduce 9-fluorenone to 9-fluorenol and monitor the reaction at several time intervals by TLC.
O HO H

NaBH4 MeOH Fluorenone 9-Fluorenol

Procedure: Bring a watch, a metric ruler, and a pencil to lab. Obtain a hotplate, and a heat transfer block from the storeroom. Place the magnetic spin vane into your 5 mL conical reaction vial with the point down. Add approximately 200 mg of 9-fluorenone (pre-weighed) and 4 mL of anhydrous methanol into the vial. Put the vial into the heat transfer block (sitting on the hotplate/stirrer) and stir until all of the 9-fluorenone has dissolved. Mark the two TLC plates in pencil as shown below.

1 = f luorenone 2 = f luorenol 3 = t0s 4 = t30s 5 = t60s 6 = t120s 7 = t240s 8 = t600s


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Label two 12x75 culture tubes as fluorenone and fluorenol and add a few (~ 1 mg) crystals of fluorenone (starting material) and fluorenol (reduction product) to the appropriate tube. Add 500 L of acetone to each tube to make a solution of the known samples and use two spotting pipettes to spot lanes 1 and 2 as shown above. In a separate 12x75 culture tube, obtain approximately 20 mg of NaBH4 (do not add this to the reaction mixture yet). As the reaction progresses you will take samples of the solution at times

0, 30, 60, 120, 240, and 600 seconds. Timing is important in this experiment, so make sure you understand the procedure and have supplies prepared before you begin the reaction. Using a spotting pipet, spot a sample of the reaction solution (before addition of the sodium borohydride) in lane 3 designated t0s (time zero). Using your watch, monitor the time and transfer the sodium borohydride to the reaction vial. At times =30s, 60s, 120s, 240s, and 600s spot lanes 4 through 8, respectively. After the last spot, develop your two TLC plates using methylene chloride as the developing solvent. Use UV light to visualize the plates. Trace any spots visualized with a pencil. After you have developed and marked your TLC plates, isolate the 9-fluorenol from the reaction mixture by transferring the reaction solution to a 10 mL Erlenmeyer flask and adding approximately 2 mL of water. What affect does adding water have on the product solution and why? Heat the mixture to approximately 100 C on your hotplate until solid dissolves completely in solution. When your solid is dissolved, remove the flask from the hotplate. Remove the Erlenmeyer from the hotplate and let it cool to room temperature. Once it has cooled to room temperature, carefully place it in an ice bath to complete the crystallization of the 9-fluorenol. In general, why is re-crystallization of a product preformed? Remember to clamp your securely clamp your vacuum flask and to pre-wet your filter paper with a small about of ice cold water. Collect the product using vacuum filtration with a Hirsch funnel fitted with a 1.5cm diameter filter paper wetted with water. Using 1 mL of ice-cold water, rinse the Erlenmeyer flask and add to the filter. Continue pulling vacuum on the filter for 5 minutes. Transfer the crystals to a tared piece of piece of filter paper and place this on a watch glass in your drawer to dry for 24 hours. After the product has dried, weigh the product, and determine percent yield and melting point of the product. What is the expected melting point of 9-fluorenol? How does this compare with your experimental melting point range? Transfer the product to a labeled product vial and place in the glassware container above your fume hood. Post Lab: Include the material required in the Lab Expectations handout. Tape a properly labeled TLC plate to the observations section of your lab report.= Answer the following questions separate from your conclusions. 1. Describe the conclusions that you can deduce about the reaction based on your TLC analysis of the reaction (i. e. the extent and time course of the reaction). 2. Describe how the control samples helped you understand the results of your TLC analysis. 3. What is the significant difference between 9-fluorenone and 9-fluorenol that allows reaction progress to be monitored by TLC? 4. Give an example of how you would take a primary alcohol to an aldehyde, what reagents would you use? How would you take a primary alcohol to a carboxylic acid? 5. Show the reactant and product for reduction of benzaldehyde with NaBH4.

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