A variety of nonnitrogenous oxygenated compounds gave false-positive alkaloid reactions with Dragendorff's spray reagent. These compounds reacted positively if the oxygen function and the β-carbon bonded to the oxygen had high electron density. Thus, aldehydes, ketones, lactones, ethers, esters, epoxides, and peroxides with an ethylene bond or free alkyl groups at the β-carbon gave a positive reaction, provided that the availability of electrons at the oxygen and the β-carbon was not altered by electron withdrawal or hydrogen bonding. Carbonyl, ether, and ethylene functions were shown by IR evidence to be involved in coupling. Nitrogen-free, alkaloid-like acetone artifacts were obtained by interaction with fixed alkali and with acids. These compounds were postulated to be α,β-unsaturated aldol condensation products of acetone. Interaction with ammonia in addition yielded nitrogenous alkaloid-like artifacts.