231L Ketone Reduction

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Feb 20, 2024

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NEW TEMPLATE: 231L Sodium Borohydride Reduction Pre-lab Questions     Procedure and Safety  1. (10 pts) Write a VERY brief bullet point list summary of the procedure. Synthesize (TCL) Separate and purify (DCM) Characterize, (mass, melting point, FTIR) 2. (18 pts, 3 pts ea) Fill in the following table with amounts to use to make 10 mL of each of the TLC developing solvents you will test.    % Ethyl Acetate/% Hexanes   Volume Ethyl Acetate (mL)   Volume Hexanes (mL)   30/70 3 7 50/50 5 5 70/30 7 3     3. (84 pts) This question reviews drawing bond-line structures. In addition, you will identify the purpose for each chemical in the synthesis that you will perform for this experiment. Reading through the procedure carefully will help you identify the chemical purpose. In addition, you will add safety information for each chemical rather than writing the usual safety summary.   Compound   Structure (5 pts ea) Purpose (3 pts ea) Hazards (4 pts ea) methanol  Solvent   Do not drink. Do not use near flames  ethyl acetate  synthesis   Flammable, irritant hexanes  synthesis Flammable, enviro damaging, health hazard, skin irritant sodium borohydride   synthesis  Flammable, methylene chloride  product  toxic 9-fluorenone  synthesis  irritant
9-fluorenol   synthesis  corrosive hydrochloric acid   synthesis  irritant         Mechanism 4. The first step in the reduction of an aldehyde or ketone using sodium borohydride is a nucleophilic attack. This is shown below for the reduction of acetone. Sodium borohydride can be considered to by a source of hydride ions as shown.     a. (4 pts) What is the nucleophile in this step?   H b. (4 pts) Why is the carbonyl carbon attacked by a nucleophile? More electronegative   5. (20 pts) Draw the first step for the reaction you will do for this experiment: Reduction of 9- fluorenone using sodium borohydride.    6. (25 pts) The second step for the sodium borohydride reduction of an aldehyde or ketone is a proton transfer step. This is shown below for the reduction of acetone.   
  Draw the proton transfer step for the reduction of 9-fluorenone using sodium borohdride.    Amounts to Use 7. (10 pts) Fill in the following table with amounts to use and theoretical yield for this experiment. Show work for credit.        Starting Material   Reagent   9-fluorenone  Sodium borohydride  Moles   1.4 mmol   0.7 mmol   MW   180.20 g/mol   37.83 g/mol   Amount    ? ? Data and Observations 1. (15 pts) Insert a photo of your three TLC plates used for testing developing solvents with provided solutions of 9-fluorenone and 9-fluorenol. The solvent front should be marked, and circles drawn around any spots visualized using UV light. Plates should be clearly labeled with developing solvent used and what was spotted. Photo should include a ruler for calculating R f values.
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2. (5 pts) Mass of 50 mL Erlenmeyer flask________ 3. (5 pts) Mass of 50 mL Erlenmeyer flask and 9-fluorenone__________ 4. (5 pts) Mass of 9-fluorenone______0.210______ 5. (15 pts) Insert photo of TLC plate showing reaction progress. The solvent front should be marked, and circles drawn around any spots visualized using UV light. Plates should be clearly labeled with developing solvent used and what was spotted. Photo should include a ruler for calculating R f values.
6. (5 pts) Mass of rotovap flask___88.814_______ 7. (5 pts) Mass of rotovap flask and product_____89.012_______ 8. (5 pts) Melting point of product____148-150C_________ 9. (20 pts) Insert a photo of your FTIR spectrum for your product. Draw the structure of 9-fluorenol on or near the spectrum. Label the peaks in the spectrum which correspond to functional groups in your product.
Analysis and Application Questions Analysis 1. (15 pts) Calculate the percent yield. Show your work. Reactant Product 9-fluorenone 9-fluorenol Mass .210 0.198 MW 180.20 g/mol 182.22 g/mol Moles 0.001165 0.0009220 Since one mole of reactant yields one mole of product: Percent Yield = (mole product /mole reactant) x 100 79.141 % 2. (5 pts) Calculate the R f values for the spots on the TLC plate used for testing solvents. Only calculate for spots on plate showing best separation. 3. (5 pts) Calculate the R f values for the spots on the TLC plate showing reaction progress. Comment on whether your TLC showed that your reaction was complete or not. 4. (20 pts, 10 pts for specifically explaining how each type of data supports claim) Was your synthesis of cyclohexanol succussful? Explain. Use your FTIR, and melting point data as evidence in your explanation. Remember that you need to be specific when using data as
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evidence of your claim of success or lack of success. If you were unsuccessful, make a specific suggestion for what you would do differently to get better results. The FTIR test matches what we can expect from the product, with a peak just over 3000, and peaks at 1500, 1000, 700. The peak at 3000 is indicating an O-H stretch. The melting point was also what we expect from the product, so in the end this lab was successful.