Elimination of D20 from deuterated 4 affords the abundant ion at m\e 270. As expected only one molecule of D20 is lost since the second hydroxyl group is attached to the aromatic ring. In contrast, the cardenolide, digitoxigenin (5), affords a CI(D20) spectrum containing peaks corresponding to the successive loss of D20 and HDO from the d2-5 + D+ion.In addition to the above examples, we have also obtained Cl (D20) spectra on a number of compounds containing one or more common organic functional groups. Our findings indicate that hydrogen bonded to heteroatoms in alcohols, phenols, carboxylic acids, amines, amides, and mercaptans undergoes essentially complete exchange in the ion source when D20 is employed as the reagent gas at a pressure of 0.4 Torr. Small amounts of deuterium incorporation (<15%) occur in some ketones, aldehydes, and esters but, in general, this does not complicate the analyses. At the usual sample pressures (<10"e Torr) unsaturated compounds such as benzene, stilbene, and 3,3-dimethyl-l-butene fail to undergo exchange in the ion source.In summary, the above results indicate that CIMS using D20 as the reagent gas provides a convenient method for determining the active hydrogen content of organic molecules.Abundant ions in the molecular weight region are usually observed in CI(D20) spectra and the method of exchange minimizes isotope and sample losses.