“Freddie,” a college student diagnosed with schizophrenia, seeks guidance from his psychiatrist, “Dr. Ruiz,” following a relapse due to non-adherence to his prescribed medication regimen. To improve Freddie’s treatment plan, Dr. Ruiz suggests transitioning to a longer-acting injectable form of his current medication, despite Freddie’s fear of needles. The new medication is a fatty acid ester derived from the original drug whose extended activity is due to its greater lipid solubility and subsequent hydrolysis within the body. The case engages students with questions designed to teach and reinforce fundamental concepts in organic chemistry. It also illustrates how organic chemistry is used in drug design that can lead to improved health outcomes. The case is intended for use in the second semester of a college-level organic chemistry course after lectures on the chemistry of esters. It can also be used in medicinal chemistry or pharmaceutical chemistry classes, offering students a real-world perspective on the intersection of organic chemistry and healthcare.