Alternating copolymerization offers an ideal method for introducing certain pairs of functional groups into copolymer chains in a controlled manner. In a previous paper from this laboratory, a novel copolymer containing alternating imidazole and hydroxamic acid functional groups was reported, and its evaluation as a synthetic enzyme was described. In an extension of this work, the present paper reports the synthesis, characterization, and evaluation of those novel copolymers containing alternating imidazole and phenolic hydroxyl functional groups. The results of this study indicate that “cooperativity” between this pair of functional groups is somewhat restricted, probably for reasons related to the conformation of the copolymer chains or the proximity of the functional groups to the copolymer backbone.