Procedural and assessment updates to the classic bleach oxidation of 4-tert-butylcyclohexanol to 4-tert-butylcyclohexanone are described. Specific modifications include monitoring of the reaction by thin-layer chromatography (TLC), analysis of the crude product by IR, GC-MS and 13C-APT NMR data, and investigation of the active oxidant and structure of the product by computational chemistry. Each modification promotes deeper student learning of the practical and theoretical concepts of the exercise.
Esselman et al. (Thu,) studied this question.