What are the rules, in organic chemistry, that determine whether an oxidation is mild or strong?

I know that potassium dichromate is a strong oxidizing agent and it can remove two hydrogen atoms from a primary alcohol to form an aldehyde.

So is strong oxidation (in organic chemistry) when more than one hydrogen atom is removed i.e. when oxidation is greater than the removal of just one electron?


closed as too broad by airhuff, Jon Custer, NotEvans., Todd Minehardt, Buttonwood May 31 '17 at 21:21

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    $\begingroup$ No, these are totally unrelated things. $\endgroup$ – Ivan Neretin May 31 '17 at 8:13
  • $\begingroup$ The ease of an organic redox reaction to occur correlates with the difference of electrode potentials between the half reaction of oxidation, and the one of reduction. Hence, for example, $\ce{KMnO4}$ a more powerful oxidising agent under acidic, than under neutral or basic conditions (related: chemistry.stackexchange.com/questions/73350/…). $\endgroup$ – Buttonwood May 31 '17 at 21:20

If this is a serious post, which is not easy to believe, then: Mild = sufficient or inadequate, depending on context. Strong = adequate or excessive, depending on context. There is no "rule", feel free to make your own. It needs to be consistent, however, and that is a problem since what is mild in one reaction context will be too strong in another. Also note that many organic reactions can be done electrochemically, which means the requisite potential can be determined. Unfortunately, oxidizing agents aren't one-dimensional. That is, their reactivity isn't based simply on their ability to accept electrons. Instead specific (element or group) interactions (additions, abstractions, substitutions, rearrangements) also matter. For example a reagent which had only a moderate tendency to oxidize but had a high tendency to add a particular group might be considered a "strong" oxidant.


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