[a13b13]

In the oxidation of cyclohexanol to cyclohexanone NaOCl and acetic acid are used. I'm wondering if the actual oxidizing agent here would be considered HOCl or NaOCl?

[camptzak]

Im pretty sure that HOCl protonates the alcohol then NaOCl does an Sn₂ substitution reaction releasing water. the water then grabs the proton that is attached to the carbon that is attached to the OCl and the lone pair comes up forming the carbonyl and releasing a chlorine ion.
does that answer your question?

[a13b13]

Kind of, I have this practice quiz question that is asking if the oxidizing agent is HOCl or NaOCl and I'm just kind of confused because they both participate in the oxidation.

[Dan]

Im pretty sure that HOCl protonates the alcohol then NaOCl does an Sn₂ substitution reaction releasing water.

Can you provide a reference for this?

Normally this is drawn as a transfer of electrophilic chlorine to the alcohol O followed by elimination of HCl, like this:

[a13b13]

Thank you, Dan. That was very helpful!