Solution

ID: past-exam-of-the-chemistry-course-of-the-year-4-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-2/section-i/34/a/solution

The product is 1,3,4-Oxadiazole. Protonation or phosphorylation activates one formyl carbonyl of the diacylhydrazine. The oxygen of the other carbonyl attacks intramolecularly, closing a five-membered ring containing the atom sequence O–C–N–N–C. Proton transfers and loss of water produce the conjugated ring; deprotonation restores the neutral aromatic heterocycle.
The overall transformation is . Polyphosphoric acid provides carbonyl activation and an acidic medium. PO acts as a strong dehydrating agent, consuming water and maintaining the condensation-driving environment. Neither nitrogen is expelled, and the oxygen retained in the heterocycle originates from a carbonyl rather than an inserted reagent oxygen.

New to topics? Read the docs here!