Catalytic oxidation of alcohols

Exercise 2

    

catalytic oxidation of a primary alcohol generally leads to a mixture of aldehyde and carboxylic acid, that of a secondary alcohol to a ketone. This oxidation is often not complete. How many different substances do you suspect in the mixture resulting from the catalytic oxidation of the racemic mixture of propan-1,2-diol and which?

This mixture may contain nine different substances (!): (R) - propane-1,2-diol and (S) - propane-1,2-diol (R) - 2-hydroxypropanal and (S) - 2-hydroxypropanal (R) - 2-hydroxypropanoic acid and (S) - 2-hydroxypropanoic acid hydroxypropanone 2-oxopropanal 2-oxopropanoic acid (see the →       Table organic functions )