Abstract
Oxidation of an alcohol to the aldehyde or ketone, and corresponding reduction back to the alcohol, are two of the most common transformations of preparative organic chemistry. As such, they have a place in the undergraduate laboratory course. We have found the exercises currently available in laboratory texts to be deficient in several ways: the oxidized products [camphor, cyclohexanone] are volatile and difficult to isolate, and do not visualize on TLC. While camphor is a solid, it is difficult to isolate and crystallize. We have found a much more satisfactory combination in 4-nitrobenzyl alcohol and 4-nitrobenzaldehyde. both are crystalline, neither is volatile, and both are strongly UV-absorbing, so they visualize well on TLC.
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