The synthesis, characterization, and evaluation of bifunctional synthetic enzymes via alternating copolymerization was carried out. It was desired to obtain copolymers containing alternating placements of complementary functional groups to determine whether “cooperativity” between the groups (in the hydrolysis of ester substrates) would be greater than in the corresponding random copolymers containing the same functional groups. The bifunctional alternating copolymer, N-(β-vinyloxyethyl)imidazole-N-hydroxymaleimide, was synthesized and evaluated as a catalyst in the hydrolysis of p-nitrophenyl acetate. The effectiveness of this copolymer as an esterolysis catalyst was compared with imidazole and the homopolymer of N-hydroxymaleimide. Monomer syntheses, polymerization, and copolymer properties are also reported.