I have never understood which agent will be able to oxidize or reduce which type of reactants and yield which type of products will be formed. For example I want to know about DIBAL-H and how is it able to reduce some groups but not carboxylic acid. Here is what all I want to know:

  1. What are the criteria for judging which agent will oxidize or reduce?

  2. What will be the condition in which it will be able to oxidize or reduce a given molecule.

  3. What type of products will be formed?

Note: I am in high school and thus need an explanation which I will be able to understand.


closed as too broad by Mithoron, a-cyclohexane-molecule, Todd Minehardt, A.K., Tyberius Aug 28 '18 at 14:55

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  • $\begingroup$ Are you looking for a qualitative or quantitative criteria? Reduction potentials would give an easy quantitative measure, but qualitative measures are much more specific to the systems you are studying. @Pan $\endgroup$ – Tyberius Aug 28 '18 at 14:54
  • $\begingroup$ I am more interested in the qualitative measure @Tyberius $\endgroup$ – Pan Sep 8 '18 at 7:08

This goes to the heart of organic chemistry and most of it is just about learning the properties of the most common reagents, then understanding where to find the detailed information. A good Organic chemistry text book is the starting point, then there are lists to help, for examples list of oxidising agents, list of reducing agents or entire series of books on Organic chemistry reagents e.g. Fieser & Fieser which a good library should have. For individual transformations databases such as Reaxys or Scifinder are searchable by structure and can find the conditions under which a transformation has previously been done. If the transformation has not previously been reported then you have to use your judgement as to which conditions to try, that is where the real art of synthesis comes in. It is important to note that solvent and temperature play a huge role in such transformations. Reactions that proceed in one solvent may give a different outcome in another.

Dibal-H does reduce carboxylic acids, but require multiple equivalents and elevated temperature or additional reagents such as TMSiCl paper here

  • $\begingroup$ Thank you for answer. But i think there is no intuitive for me to say if or not oxidation will happen at my high school level. $\endgroup$ – Pan Aug 24 '18 at 17:05
  • $\begingroup$ Probably not, just learn the reactions of the most common reagents and those will provide the answers at the high school level. $\endgroup$ – Waylander Aug 24 '18 at 17:54

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