So in lab, I was to oxidize 9-fluorenol to 9 fluorenone. The chemicals I used were: 100 mg. of 9-fluorenol in 6mL of acetone. 0.25 mL of glacial acetic acid and 1.2 mL of a 5.25% sodium hypochlorite solution.
My question is if I attempt to oxidize 9-fluorenol by adding only bleach and acetone, can I expect the experiment to yield 9-fluorenone? Explain.
Were all necessary reagents added?
My guess is that I can still yield 9-fluorenone because the bleach contains the oxidizing agent Cl? I don't understand what the glacial acetic acid does. Nor do I understand the difference between glacial acetic acid and acetic acid ( i already read wikipedia but still confused). Please help and thank you. I really appreciate any help and admire your knowledge.
The hypochlorite is the oxidizing agent and that is OCl^- and not Cl^- nor Cl2. Furthermore, HOCl oxidizing power is controlled somewhat by the acidity of the mixture. The half reaction for the OCl^- acting as an oxidizing agent is
OCl^- + 2e + 2H^+ ==> Cl^- + H2O
so the solution should be acid. That is the part that glacial acetic acid plays. Glacial acetic acid is concentrated acetic acid (about 99% acetic acid) as opposed to a laboratory reagent acetic acid which might be 6 molar or even weaker.
To determine if adding only bleach and acetone will yield 9-fluorenone, let's break down the reaction and analyze the role of each reagent.
The oxidation of 9-fluorenol to 9-fluorenone typically requires an oxidizing agent, which in this case is sodium hypochlorite (bleach). Sodium hypochlorite contains the oxidizing agent chlorine (Cl), which can carry out the oxidation reaction.
The presence of acetone in the reaction mixture is likely to act as a solvent. Acetone is a common solvent used in organic chemistry, and it facilitates the dissolution of the reactants and products.
Now, let's discuss the role of glacial acetic acid. Glacial acetic acid is essentially concentrated acetic acid, meaning it is acetic acid in its pure form at a low temperature. Acetic acid is a weak acid, and its addition to the reaction mixture serves multiple purposes:
1. It can act as a catalyst by protonating the 9-fluorenol. Protonation increases the electrophilicity of the alcohol group, making it more susceptible to nucleophilic attack by the oxidizing agent.
2. It can help create an acidic environment. An acidic pH is favorable for the oxidation reaction, as it can stabilize the oxidizing agent and promote the formation of intermediates.
3. It acts as a solvent as well, aiding in the solubility of the reagents and products.
Now, back to the question of whether you can still yield 9-fluorenone by adding only bleach and acetone. While bleach contains the oxidizing agent needed for the reaction, without glacial acetic acid, the reaction might proceed at a slower rate or might not proceed at all. The glacial acetic acid enhances the reaction by providing acidity and catalytic properties. Therefore, the absence of glacial acetic acid could potentially impact the yield or completion of the reaction.
In conclusion, it is difficult to predict the outcome of the reaction without glacial acetic acid, but it is possible that the reaction might not proceed as expected or might yield a lower amount of 9-fluorenone. Ideally, it would be best to follow the established protocol which includes all the necessary reagents and conditions for a successful oxidation reaction.