The chemoselective oxidation of secondary alcohols to ketones using bleach and acetic acid has found utility in the organic chemistry laboratory curriculum. However, the incorporation of oxidations with complementary selectivity into laboratory exercises have not been described. We report a series of three, bleach-based, oxidation reactions on a mixture of 1-butanol and cyclohexanol providing distinctly different products as analyzed by gas chromatography. These reactions include the (1) selective oxidation of cyclohexanol to cyclohexanone; (2) selective and mild oxidation of 1-butanol to butanal; and (3) nonselective and complete oxidation of cyclohexanol and 1-butanol to cyclohexanone and butyric acid. These reactions expand the alcohol oxidations available for discovery-oriented organic laboratory activities.

Extending the scope of alcohol oxidations in discovery-oriented organic chemistry laboratories

256th National Meeting (2018)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.