The selected ion flow tube (SIFT) technique has been used to investigate the ion-molecule reactions of several ions with the neutral molecules ethylene oxide, CH 2 OCH 2 -c, and propenal, CH 2 CHCHO. Both molecules have been identified in hot-core star forming regions [1, 2]© and have significance to astrochemical models of the interstellar (ISM) and circumstellar medium (CSM). Moreover, the molecules contain functional groups, such as the epoxide group (ethylene oxide) and an aldehyde group, which are part of a conjugated -electron system (propenal) whose reactivities have not been studied in detail in gas-phase ion-molecule reactions. The larger recombination energy ions, Ar ϩ and N 2 ϩ , were reacted with the neutrals to give insight into general fragmentation tendencies. These reactions proceeded via dissociative charge-transfer yielding major fragmentation products of CH 3 ϩ and HCO ϩ for ethylene oxide and CH 2 CH ϩ and HCO ϩ for propenal. The amino acids glycine and alanine are of particular interest to astrobiology, especially if they can be synthesized in the gas phase. In an attempt to synthesize amino acid precursors, ethylene oxide and propenal were reacted with NH n ϩ (n ϭ 1-4) and HCNH ϩ . As might be expected from the proton detachment energies, NH ϩ , NH 2 ϩ , and HCNH ϩ reacted via proton transfer. NH 3 ϩ reacted with each molecule via H-atom abstraction to produce NH 4 ϩ , and NH 4 ϩ reacted via a ternary association. All binary reactions proceeded near the gas kinetic rate. Several associated molecule switching reactions were performed and implications of these reactions to the structures of the association products are discussed Ikeda et al. and Hollis et al. (J Am Soc Mass Spectrom 2007, 18, 445-452)