The interactions of diethyl ether with the Si(100) surface have been examined computationally, using ab initio and density functional theoretical techniques, as well as experimentally, using Auger electron spectroscopy and thermal desorption spectroscopy. This surface appears to be relatively inert with respect to reaction with the ether functional group. The reaction paths available to diethyl ether on Si(100) can be contrasted to the interactions of this surface with alcohols and amines, both of which can undergo facile addition reactions upon interacting with this surface. The interactions of ether molecules containing additional, more reactive functional groups, such as a C=C bond, with the silicon surface will also be discussed. .