The Design of Laboratory Experiments in the 2000’s

Last week we did a variation of the oxidation of alcohols with household bleach (sodium hypochlorite) experiment. In the past we have used isoborneol as our alcohol which gave the distinctive smelling solid camphor. This year we had a series of 2, 3, or 4-methyl-1-cyclohexanols as our starting materials so the products were liquid 2, 3, and 4-methyl-1-cyclohexanones. I found an article in JCE on entitled “The Design of Laboratory Experiments in the 1980’s: A Case bleachStudy on the Oxidation of Alcohols with Household Bleach” authored by Mohrig, Nienhuis, Linck, Van Zoeren, Fox, and Mahaffy that described the evolution of the bleach oxidant experiment from a Journal of Organic Chemistry article (Stevens, Chapman, and Weller, J. Org. Chem., 45, 2030 [1980]) to a popular undergraduate experiment. I included the original JOC article in the student handout. I wonder if this experiment has evolved further since the 1980’s, or is it simply repeated once it gets published in a laboratory manual. What other experimental procedures are taking that path from research journal article to JCE to the undergraduate lab? The oxidation of cyclohexene to adipic acid with hydrogen peroxide and sodium tungstate dihydrate has a similar story. I suppose most undergraduate labs have some roots in the formal chemical literature, but their “stories” have been largely lost.

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