Automated mechanism generation was used to study the condensed-phase oxidation of decane and octane as a means to gain insights into the degradation of lubricating oils. Part 1 of this series established a library of structure-reactivity relationships that enables the estimation of all kinetic data required for solving large reaction mechanisms that model lubricant degradation. Specific reaction rules are proposed that enable automated mechanism generation to be used, for the first time, to study condensed-phase free-radical oxidation of large substrates. Models of decane oxidation were generated, and good agreement with available experimental data was achieved. The optimized parameters were then used to generate predictive models of octane autoxidation.