The concurrent use of one-dimensional (1 H-NMR) and two-dimensional (1 H-1 H-COSY and 1 H-1 H-Delay-COSY) experiments can unambiguously assign each resonance in a spectrum to a particular proton. We have developed an experiment for the advanced chemistry student that utilizes long-range coupling to assign signals in the spectra of ketopinic acid, borneol, and isoborneol. Prelaboratory discussion of the spectra of camphor, hands-on use of the instrumentation, and determination of molecular stereochemistry are topics visited during the course of this experiment.
Roark et al. (Sat,) studied this question.