SOLVED:The structure of the bicyclic monoterpene borneol is shown in Figure 25.8. Isoborneol, a stereoisomer of borneol, can be prepared in the laboratory by a two-step sequence. In the first step, borneol is oxidized to camphor by treatment with chromic acid. In the second step, camphor is reduced with sodium borohydride to a mixture of 85 % isoborneol and 15 % borneol. On the basis of these transformations, deduce structural formulas for isoborneol and camphor.

Borneol: Oxidation of Borneol, Final Product Isolation

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