We report the controlled radical polymerization of 2-vinyl-4,4-dimethyl azlactone (VDMA), a 2-alkenyl-2-oxazolin-5-one monomer that contains a polymerizable vinyl moiety and a highly reactive, pendant azlactone, as well as dilute solution properties and surface attachment and functionalization. Reversible addition-fragmentation chain transfer (RAFT) was used to polymerize VDMA in benzene at 65 degrees C using either 2-(2-cyanopropyl) dithiobenzoate (CPDB) or 2-dodecylsulfanylthiocarbotlylsulfanyl-2-methylpropionic acid (DMP) as RAFT chain transfer agents (CTAs). The pseudo-first-order kinetics and resultant well-defined polymers of low polydispersity indicate that both CTAs afford control over the RAFT polymerization of VDMA. Dynamic and static light scattering and small-angle neutron scattering (SANS) were performed to determine the weight-average molecular weight, radius of gyration, and second virial coefficient of VDMA homopolymers in THF. Additionally, well-defined polymers of VDMA containing carboxyl end groups were covalently attached to epoxy-modified silicon wafers via esterification to produce polymeric scaffolds that can be subsequently functionalized for various bio-inspired applications.