As the question says, I'm supposed to make cyclohex-4-ene-1,2-diol using cyclohexa-1,4-diene:
I can use any inorganic reactant, any solvent, and any organic molecule with 3 or fewer carbons. I am not sure how to go about this question, as I do not know how to use regional-specific reactions. Any help, even just mentioning a reaction mechanism I can use for this would be greatly appreciated.
I could put the cyclohexa-1,4-diene on $\ce{KMnO4}$ for a catalyst and $\ce{H2O}$ with $\ce{HO-}$ as solvents in order to break the double bond and replace it with the $\ce{HO-}$ molecules. Problem is that this would affect the molecule as a whole – not just a specific side which is what I need.
I also thought of using bromine as something temporary, since they are easy to remove however, again, this affects the whole molecule.
I also thought about Diels-Alder reaction, but we haven't learned anything about that so I do not know how to use it- much less on a cyclic molecule.
I have also seen the osmium tetroxide oxidation of alkenes. However, I still have the problem that I can't control this reaction to only affect one side.