To generate a list of candidate compounds for this simulated reaction, we considered all probable products of the oxidation of heptane (4a): compounds with a hydroxyl group at each nondegenerate carbon atom, ketones at each nondegenerate carbon, and aldehyde and carboxylic acid groups at the terminal carbons (4b-j). In total, the candidate library comprised 10 compounds. Three unique regions of the spectrum were identified by considering their spectral information as described in the Methods above. These regions were used sequentially to deconvolute the experimental The first region of interest identified by the spectral information content procedure was the downfield region with chemical shift greater than 8 ppm. Analysis of this region revealed whether heptanal or heptanoic acid (4c and 4j) was present in the spectrum. From a first iteration of the HMCMC procedure, both compounds 4c and 4j were excluded. Next, the information-dense region of the spectrum between 3-4 ppm was analyzed. In the library of candidate spectra, all peaks in this region corresponded to a methine proton α to a hydroxyl group. Thus, the presence or absence of peaks in this region revealed the presence or absence of 1-heptanol (4b), 2-heptanol (4d), 3-heptanol (4f ), and 4-heptanol (4h). From an iteration of the HMCMC procedure, compounds 4f and 4h were removed from the list of components.