The first results of the effect of monochromatic soft x-ray exposure of self-assembled monolayers (SAMs) of iodomethylphenylsilyl groups chemisorbed on the native oxide surface of a Si substrate are presented. The SAMs, combined with a subsequent selective metallization process, have already been shown to be an effective resist system for projection x-ray lithography and show great promise as an e-beam resist. The first conclusive evidence is presented for the loss of iodine from the SAM during soft x-ray exposure. The loss of iodine in the exposed areas allows the selective deposition of an etch resistant metal in the unexposed areas. The SAMs also provide a model system for the study of resists at the molecular level, and the role of photogenerated electrons in determining sensitivity and resolution. The concentration of iodine left on the surface during monochromatic exposure was monitored using photoemission. The loss of iodine with exposure was then fit with a double exponential. The photon energy dependence of the decay rates are measured and presented for photon energies 75-108 eV. The SAM sensitivity is shown to correlate with photoelectrons generated from the Si native oxide surface.