Module 5: Lactide Formation The cyclization of oligomeric PLA used to produce lactide (step ii, Scheme 2) reinforces many of the skills that the students learned during the oligomerization reaction, while adding a new level of complexity. Prior research has found that higher yields of lactide achievable by oligomerization of are lactic acid prior cyclization rather than from direct to dimerization of lactic acid. The advantage of this procedure is presumably due to entropic reasons. In order to obtain high yields of lactide, the cyclization relies on a short-path distillation under reduced that removes the lactide product from pressures the reaction mixture and drives the equilibrium toward the desired product 18 Under these conditions, the students learn how to design and plan a reaction setup to maximize control of parameters such as temperature and pressure (Figure S4 in the Supporting Information). The students also learn how to carry out distillation under reduced pressures. After distillation, the lactide product is obtained as a mixture of diastereomers (rac and meso) and is often contaminated with small amounts of