Is your intermediate a primary carbocation? If so, look for a 1,2-hydride or alkyl shift. Resources for Practice
C. Pericyclic Reactions and Orbital Symmetry (4 problems) 15. Predict the stereochemical outcome and mechanism (concerted step/TS drawing) for the thermal Diels–Alder reaction between cyclopentadiene and acrylonitrile; explain endo/exo selectivity. 16. Explain the product and allowedness for the electrocyclic ring-opening of 3,4-dimethylcyclobutene under thermal conditions; show orbital symmetry reasoning (Hückel/Möbius). 17. Propose a mechanism and predict products for a [3,3]-sigmatropic Claisen rearrangement of allyl phenyl ether; show stereochemical transfer. 18. Rationalize why the 6π electrocyclization of a conjugated triene proceeds thermally in a conrotatory or disrotatory manner (pick a specific triene and state outcome). advanced organic chemistry practice problems 2021
He took a gamble. He drew a massive, sweeping arrow labeled and wrote: “See mechanism in appendix (hypothetical).” It was a Hail Mary, a nod to the fact that sometimes organic chemistry required a little biological magic. Is your intermediate a primary carbocation
of recently discovered molecules. Key resources for these types of problems include Organic Chemistry Problems Pericyclic Reactions and Orbital Symmetry (4 problems) 15