Question

In regards to the synthesis of 9-fluorenone via sodium hypochlorite oxidation of 9-fluorenol (9-Fluorenol -> 9-fluorenone) lab answer the following question:

What would happen if this oxidation were carried out with 9-methyl-9-fluorenol?

Answer 1

The mechanism results in the exchange of a Cl⁺ with a H⁺ on oxygen, followed by subsequent elimination of HCl to form the ketone. H-atom is substituted by CH₃– group in 9-methyl-9-fluorenol, so the 5 th step in the mechanism, elimination of HCl is not possible, so that the final product ketone will not produce, due to lack of H.