Explore the fascinating world of isoprenoids, rubber, and polymer properties in this 46-minute lecture from Yale University's Freshman Organic Chemistry II course. Dive into the biosynthesis of isoprenoid natural products, learning how they are formed through the oligomerization of electrophilic isopentenyl pyrophosphate (IPP). Discover the commercial importance of latex and the revolutionary vulcanization process developed by Charles Goodyear. Gain insights into the curious properties of rubber explained through statistical mechanics, including its contraction upon heating when stretched. Examine how specific chemical treatments confer useful properties to various polymers, from hair to synthetic rubber and plastics. Investigate the structure of copolymers and non-Hammond behavior in free-radical polymerization. The lecture covers five key chapters, providing a comprehensive overview of isoprenoids, rubber, and the intricacies of tuning polymer properties.