# Mechanism for oxidative cleavage of tertiary alcohols by NaOCl

I came across this today

An ester $\ce{C4H8O2}$ on reaction with $\ce{CH3MgCl}$ and hydrolysis gives an alcohol. The alcohol on reaction with $\ce{NaOCl}$ and $\ce{H3O+}$ gives acetic acid. Identify the structure of the ester.

But what I'm facing a problem with is the role of $\ce{NaOCl}$. My teacher said it can cleave and oxidize a tertiary alcohol, say tert-butyl alcohol, to acetic acid.

But I couldn't understand the mechanism. Any help will be appreciated.

• There are not so many possibilities for your ester that yield an alcohol which could be oxidized to acetic acid. Which esters could you imagine from $\ce{C4H8O2}$? Sep 3 '15 at 10:02
• My problem is not with the ester...but how will NaOCl oxidize the the alcohol obtained...the mechanism..
– user14857
Sep 3 '15 at 10:04
• I don't see any evidence in SciFinder that this is an actual transformation. Can you confirm with your teacher that a simple tertiary alcohol can be oxidized to an acid? Sep 3 '15 at 20:30
• I actually think you are misinterpreting the problem, but I'll wait for confirmation about the tertiary alcohol oxidation. Sep 3 '15 at 20:32
• @jerepierre Maybe i misinterpreted what my teacher said.But it will take atleast a week before i can confirm with him.But what why did you say i'm "misinterpreting" the problem?What do you think will be the solution?What is the particular ester C4H8O2 according to you?What will be NaOCl mechanism according to you?Maybe i'm having a conceptual problem...but its always good to discuss :-)
– user14857
Sep 4 '15 at 12:58