Shale kerogen has been degraded to an organic solvent-soluble bitumen or oil by numerous methods. The various methods have been employed either to study production of oil or to gain insight into the structure of kerogen. The purpose of this investigation was to gain insight on kerogen structure by examination of the effects of strong base and nucleophilic displacement reagents on western and eastern shales. Powdered shales from the Green River and Chattanooga formations were extracted with potassium hydroxide in 1-propanol, potassium hydroxide in 1-butanol, 1-butylamine in 1-butanol, and sodium borohydride in tetrahydrofuran, all at reflux. Residual shales were extracted with benzene-methanol. The products were isolated and weighed in an effort to find a system that would degrade the kerogen to a soluble bitumen under basic, solvolytic conditions. The extraction of Green River shale with potassium hydroxide in 1-butanol gave the highest conversion (40.2 wt %) of organic carbon. The solutions containing butylamine and sodium borohydride gave small yields of product. The results from extraction of Chattanooga shale showed approximately 20% conversion with potassium hydroxide in 1-butanol while all other systems exhibited very small conversions. 21 refs., 4 tabs.