Reflection absorption infrared spectroscopy and temperature programmed desorption were used to study the adsorption of acrolein, its partial hydrogenation products, propanal and 2-propenol, and its full hydrogenation product, 1-propanol on the Ag(111) surface. Each molecule adsorbs weakly to the surface and desorbs without reaction at temperatures below 220 K. For acrolein, the out-of plane bending modes are more intense than the CO stretch at all coverages, indicating that the molecular plane is mainly parallel to the surface. The two alcohols, 2-propenol and 1-propanol, have notably higher desorption temperatures than acrolein and display strong hydrogen bonding in the multilayers as revealed by a broadened and redshifted O–H stretch. For 1-propanol, annealing the surface to 180 K disrupts the hydrogen-bonding to produce unusally narrow peaks, including one at 1015 cm⁻¹ with a full width at half maximum of 1.1 cm⁻¹. This suggests that 1-propanol forms a highly orderded monolayer and adsorbs as a single conformer. For 2-propenol, hydrogen bonding in the multilayer correlates with observation of the CC stretch at 1646 cm⁻¹, which is invisible for the monolayer. This suggests that for monolayer coverages, 2-propenol bonds with the CC bond parallel to the surface. Similarly, the CO stretch of propanal is very weak for low coverages but becomes the largest peak for the multilayer, indicating a change in orientation with coverage.