Arene Oxidation Exercises

1. Write a balanced equation for conversion of ethylbenzene and permanganate ion to benzoate and carbonate ions and manganese dioxide in the presence of hydroxide ion.

2. Would it be feasible to attempt the conversion of benzaldehyde by permanganate oxidation of toluene? Explain.

3. Would you expect a carboxylic acid to be more or less soluble in pure water than in water containing strong mineral acids ? Explain.

4. t-Butylbenzene is NOT oxidized to benzoic acid by permanganate. Why not ?

5. What effect on yield of isolated product is expected if the concentration step is omitted prior to acidification ? Explain.

6. What is the limiting reagent in this reaction ? Show how you arrived at this conclusion.

7. Why is it necessary to destroy residual potassium permanganate prior to work-up of the reaction mixture ?

8. Why is filter-aid added to the reaction mixture prior to its vacuum filtration ?

9. Why is hydrochloric acid added to the aqueous residue obtained by simple distillation ? Why might concentrated rather than dilute acid be preferred for this step ?