Solution

ID: past-exam-of-the-chemistry-course-of-the-year-3-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-3/44/b/iii/solution

A to B is a photochemical six-electron electrocyclic ring opening; B to C is a thermal six-electron electrocyclic ring closure. The broken or formed sigma bond is between the two methyl-bearing saturated carbons of the cyclohexadiene. Both transformations conserve the carbon skeleton. The light-induced and thermal processes differ in their orbital occupation and therefore in their stereochemical selection rule.

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