Reactions and interconversions of compounds in the monoterpene series have
been of great importance in studying the mechanism of carbocation rearrangements and
the stereoselectivity of various reagents and synthetic reactions. Typical monoterpenes
are the ketone camphor and the corresponding epimeric alcohols borneol and isoborneol.
In this experiment, you will reduce camphor, a naturally occurring ketone, using
sodium borohydride. Camphor is an example of a bridged bicyclic molecule: a molecule
with multiple rings that share non-adjacent atoms called bridgeheads. Camphor is a
substituted bicyclo[2.2.1]heptane. The enclosed numbers represent the size of the
“bridges” that are attached to the bridgeheads. The parent name is determined by adding
the total number of carbons in the rings.