Talk:Jones oxidation

University of Michigan study group

• Hey, I'm leading a structured study group at the University of Michigan and as part of our assignment we'll be expanding various articles in the list of organic reactions. My group has chosen to expand this site. We are planning on adding the following sections: History, Mechanism (we're hoping to have an animation to demonstrate this), Relevant Spectroscopy, and Applications. We should have our finished product up some time in April I'm guessing. We're all new to wikipedia so any advice would be appreciated! UMich215SSG (talk) —Preceding undated comment added 16:01, 2 February 2011 (UTC).
• I've noticed from a lot of discussion pages that many of the editors dislike how we work on the pages in sandboxes and then go live one day (thus preventing constructive criticism during the editing process). However I still think at that this point working in a sandbox is better (to not clutter up wikipedia with our "rough" edits), I do welcome other editors to look at our sandbox which can be found on my userpage and leave comments in the discussion. It would be interesting and helpful to get outside opinions. UMich215SSG (talk) 20:00, 16 February 2011 (UTC)

The problem that I have is the Michigan method of dumping one giant revisions onto Wikipedia, whether it is well received or not. That practice, which you employ for your convenience, is not how things are done here: We make incremental edits and discuss and debate these individual changes. In my experience several of the Michigan edits have been inferior technically and in terms of stylistic aspects. These problems do not arise with incremental, consensus guided editing. So I urge you and your fellow students to cooperate with our style of consensus-driven incremental changes, vs forcing the Michigan way on the rest of us. Again, we realize that you groups have only good intentions.--Smokefoot (talk) 00:12, 17 February 2011 (UTC)

Comments for Team History

• I'd like to see some more citations in your final draft. In the sandbox I put in an example of a citation for your reference. UMich215SSG (talk) 19:18, 3 February 2011 (UTC)
• You can add that Jones discovered the reaction in 1946. The citation for this is Oxidation of Alcohols to Aldehydes and Ketones by Gabriel Tojo. I found it on Page 5 on Google Books. Here's a link : http://books.google.com/books?id=O6USLyDIBOUC&printsec=frontcover&dq=Oxidation+of+Alcohols+to+Tojo&hl=en&ei=pzhLTeKjNI72gAfskPkk&sa=X&oi=book_result&ct=result&resnum=1&ved=0CCcQ6AEwAA#v=onepage&q&f=false — Preceding unsigned comment added by Flpngns92 (talk • contribs) 23:23, 3 February 2011 (UTC)

• Hi Team History, in your section i would also try to be a bit more neutral in your descriptions. for example if you are going to write that Jones "was one of the most influential scientists of his generation" you will need to follow up with why you feel that way? is is the prevalence of this reaction? did make a contribution that if it was not available in his time, would have limited important advancements in medicine, health, materials development? You need to remember that WIkipedia is written in a neutral point of view. good luck. MichChemGSI (talk) 23:02, 11 April 2011 (UTC)

Comments for Team Mechanism

• Nice mechanism! Glad to see you figured out how to post pictures. Did you guys learn the oxidation states of Chromium in lecture? I think it'd be cool to add those into the final mech. UMich215SSG (talk) 04:25, 9 February 2011 (UTC)
• We added the oxidation numbers in the picture in blue font.
• Also, I noticed you deleted the simple reaction scheme that was present before.... that still might be useful. Consider a setup like Swern oxidation. But again, this is your guys' wiki page, so its all up to your discretion. UMich215SSG (talk) 05:56, 9 February 2011 (UTC)
• I think the general mechanism fits somewhere in the introduction section so i moved it there for now.
• Cool, don't forget to include citations! UMich215SSG (talk) 19:54, 16 February 2011 (UTC)

Comments for Team Applications

• "Paved the way for further developments such as Collins Reaction and pyridinium dichromate.."

http://www.organic-chemistry.org/namedreactions/jones-oxidation.shtm Kitswimmer (talk) —Preceding undated comment added 23:27, 3 February 2011 (UTC).

Reagent stability

I can't find a ref at the moment, but would be useful to comment on whether the Jones reagent is reasonably stable or if instead it needs to be prepared and used right away. Acetone is already in the carbonyl form, so it can't oxidize directly. However, mixtures of acetone and sulfuric acid are not particularly stable, presumably due to acid-catalyzed aldol-like reactions within a few hours to days even at low temperatures. If the solvent is a key factor in the reaction, "reactions of the solvent" would affect its...whatever-it-does...and regardless, create purification complications. DMacks (talk) 15:08, 25 April 2011 (UTC)

Mechanism

@Emanresucamit: Cr(VI) oxidations do not involve 3-coordinate CrO₃, I am pretty sure. Protonation of that highly electron-deficient species is also questionable. Instead chromate esters are involved. They have the formula [O₃Cr-OR]^- intermediates. See doi=10.1002/0471264180.or053.01.--Smokefoot (talk) 21:29, 23 June 2020 (UTC)