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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Cavve on April 08, 2019, 11:39:20 PM

Title: What is the role of p-benzoquinone in Wacker oxidation?
Post by: Cavve on April 08, 2019, 11:39:20 PM

I was hoping that someone could help me, by clearing up my confusion by providing a somewhat detailed explanation of the role of p-benzoquinone, in terms of the mechanism it uses to regenerate Pd(0) to Pd(II). Typically, CuCl2 is used for this role, so why would one use this benzo, and how does it work? What other roles might p-benzoquinone play? I've heard as a source of oxygen??

Please and thanks,

Title: Re: What is the role of p-benzoquinone in Wacker oxidation?
Post by: kriggy on April 10, 2019, 01:22:10 AM

I would say that benzoquinone is reduced to hydroquinone and it oxidizes the Pd back to Pd²⁺. Im not sure why they use this over the copper but I can see multiple reasons such as
a) enviromental concerns: its probably easier to disopose the quinone than the heavy metal co-catalyst
b) it just works better in the specific cases

dou you have literature example of this specific example?