Oxidation of Cyclohexanone Exercises

1. Why is the reaction mixture made alkaline ?

2. Why does acidification of the concentrated reaction mixture cause precipitation of

hexanedioic acid ?

3. Why is filter aid used ?

4. Write the balanced equation for the oxidation of cyclohexanone to dipotassium

hexanedioate by basic potassium permanganate. Show all work.

5. What transformation must the ketone undergo before it is attacked by permanganate

ion ?

6. What is the limiting reagent in this reaction ? Why do you think this reagent rather

than the other was made limiting ?

7. Why is it important to destroy all of the potassium permanganate before work-up of the

reaction mixture ?

8. Write the reaction that occurs between sodium bisulfite and potassium permanganate in aqueous solution.

9. Why does the initially purple solution of potassium permanganate change color as the oxidation progresses ?

10. Why would this oxidative method for the preparation of carboxylic acids be unsatisfactory for the synthesis of pentanoic acid from 4-octanone or 4-nonanone?