The bromination of six isomeric alcohols is adapted to a discovery-based organic chemistry laboratory experiment, whereby students are provided an alcohol starting material and are charged with determining the product or product mixture produced using relevant spectroscopic data. The experiment solidifies NMR analysis skills while reinforcing the mechanistic reasoning that supports the study of organic reactions. The laboratory is highly customizable and can be adapted to align with available instrumentation to best meet the needs of students, and it has been successfully implemented at three separate universities.