Abstract: The immune system is Nature’s premier engine for the rapid evolution of molecular function, and molecular-scale information is its currency. Physical organic chemistry is the field devoted to the understanding of molecular information at its most fundamental level. These two disciplines have much to teach each other. This lecture will describe the manipulation of reliable bond-forming and bond-breaking reactions for the creation of multifunctional immunogens based on virus-like particles. I hope to show that, equipped with an informed intuition of how molecules behave, along with a heavy dose of humility, organic chemists can bring useful insights to a biological endeavor as complex as vaccine development.