We report thiol-on-gold self-assembled monolayers (SAMs) that can be photodeprotected using soft UV irradiation (lambda = 365 nm) to yield CO2H functionalized surfaces complementing those reported previously, which yielded NH2 functionalized surfaces. The photolysis of these SAMs were monitored using a combination of surface sensitive techniques. In the SAM environment the photodeprotection yields are lower than those obtained for equivalent reactions in dilute solution. The protected carboxylic acids SAMs are shown to have a low yield similar to 50% due to competing photoreduction reactions of the nitro group. The results from infrared studies show that, as the photolysis progresses, the long chain protected residues reorganize and shield the functional COOH groups, thereby reducing the hydrophilic character of the surface.