Selective Reduction of Camphor OH reduction OH borneol isoborneol The mechanism for the reduction of a ketone with sodium borohydride can be found i organic text. Creation of a new stereogenic center upon reduction of an achiral ketone i expected to result in a racemic mixture of enantiomers that are indistinguishable by NMR However, camphor is chiral. One side of the bicyclic ring is much more sterically hindered thar the other side, making it possible for an achiral reducing agent such as NaBH4 to be selective fo ny one isomer. The synthetic procedures described here are relatively simple and short, which leaves time for spectroscopy and, more importantly, for analysis. Be sure to work efficiently with your lab partner to get all of the 'wet chemistry' steps accomplished so that you can spend the extra time interpreting the NMR spectra with help from Spartan and ChemDraw Ultra
