An Oxidation Puzzle
This structure-determination experiment is used in our first semester organic chemistry course. Bleach is used to oxidize 2-ethyl-1,3-hexanediol. Under the reaction conditions, only the secondary alcohol is oxidized. The product is characterized by IR spectroscopy; the students use their IR spectra to determine the structure of the product.
Adapted from: Pelter, M. W.; Macudzinski, R. M.; Passarelli, M. E. J. Chem. Educ. 2000, 77, 1481.