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Hypochlorite Oxidation of Methyl Ketones (Haloform Reaction)

I am reacting Acetophenone with bleach in excess to form benzoic acid and chloroform.

During the reaction Sodium sulfite was used to detroy any unreacted bleach. I extracted the mixture of acetophene and bleach with 1.0 ml ether, after heating the solution and adding sodium sulfite. The reaction mixture was then acidfied adding drops of 3 Molar HCl. The white precipitate formed (benzoic acid) was collected and IR analysis was used to verify the product.

1. What is the role of sodium sulfite? How does it work? Please use an equation to explain this.

2. Why was the work-up step so important in this experiment? What can be found in the top layer, and the bottom layer in the extraction step?

3. Why was a strong acid (3M HCl) used for acidification of the alkaline phase?

4. How would a solubility test and a carboxylic acid test help to confirm that a carboxylic acid is your product?

Solution Summary

Questions relating to the hypochlorite oxidation of acetophenone are answered in detail.