Question

What is the mechanism and reaction for oxidation of an alcohol?

I had to do an experiment where I oxidize a secondary alcohal into a ketone by using sodium hypochlorite as an oxidizing reagent.

Answer 1

Consider the oxidation of cyclohexanol(C₆H₁₁OH)to cyclohexanone(C₅H₁₀CO) using sodium hypochlorite(NaOCl) in presence of ethanoic acid(CH₃COOH)  

First ethanoic acid activates sodium hypochlorite and produce hypochlorous acid which really participates in oxidation (as a result of this hypochlorous acid and sodium ethoxide is formed)

Then hypochlorous acid attacks on secondary alcohol and the hydroxyl group gets protonated ( hypochlorite ion,ClO^- remains in solution)

Next protonated hydroxyl group leaves as water, hypochlorite ion,ClO^- binds there.

Followed by proton(H⁺) elimination along with the electron transfer and chloride(Cl^-) ion elimination occurs at the same carbon.As result cyclohexanone is formed and the eliminated proton(H⁺)  and chloride(Cl^-) ion react with sodium ethoxide to form ethanoic acid and sodium chloride, ethanoic acid is regenerated.