You will apply the oxidation reaction to 9-fluorenol to obtain 9-fluorenone: 1.
ID: 907026 • Letter: Y
Question
You will apply the oxidation reaction to 9-fluorenol to obtain 9-fluorenone:
1. Describe the role of each chemical in this reaction.
Reagent
Role
9-fluorenol
H2CrO4
acetone
ether
hexanes
2. What is the actual oxidizing agent in this experiment? What is it reduced to?
3.After all of the 9-flurenol has undergone reaction, it is necessary to destroy the excess oxidizing agent in the reaction mixture. How is this done?
4. Imagine that you will monitor the reaction progress by TLC. Will the product be the higher or lower spot? What is the significant difference between 9-fluorenone and 9-fluorenol that allows reaction progress to be monitored by TLC?
Reagent
Role
9-fluorenol
H2CrO4
acetone
ether
hexanes
Explanation / Answer
1. Role of each chemical in the oxidation of 9-fluorenol to 9-fluorenone
Reagent Role
9-fluorenol Substrate/starting material
H2CrO4 Oxidant
acetone Solvent
ether solvent
hexane Extracting solvent
2. Actual oxidizing agent in the reaction is the chromic acid in Cr(VI) oxidization state. It is reduced to Cr(III) state.
3. It is necessary to destroy the excess oxidizing agent present in the reaction mixture once the reaction is complete. This is done by adding i-PrOH to the reaction mixture.
4. The reaction If monitored by tlc, will have substrate lower than the product. Alcohol is more polar than the ketone product and would stick behind on the plate.
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