The Oxidation of Primary Alcohols to Esters: Three Related Investigative Experiments

Discovery-based experiments are excellent tools for promoting substantive interaction among students and between students and instructors. Three related synthetic puzzles are described. In each case an ester is produced via oxidation of a primary alcohol by calcium hypochlorite and acetic acid. Students are placed in teams of three and a different alcohol is assigned to each member of the group. Each person in the group is responsible for synthesizing, purifying, and spectroscopically analyzing his or her unknown product. As a group, the students are asked to determine the structure of their three nonobvious products and to provide a mechanistic rationale for the transformations.