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.

Question

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.

Answer 1

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.