Solution

ID: past-exam-of-the-chemistry-course-of-the-year-4-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-1/9/a/ii/solution

The nonnucleophilic magnesium amide metalates the triazole carbon between the two ring nitrogen atoms, conventionally C5 of 1-propyl-1,2,4-triazole. That proton is more readily removed because the resulting heteroaryl anion is stabilized by the neighboring nitrogen atoms; the reagent therefore acts as a base rather than adding a tetramethylpiperidinyl group.
The heteroaryl organomagnesium intermediate attacks the allylic bromide, forming a new C–C bond. The product is 5-(cyclohex-2-en-1-yl)-1-propyl-1,2,4-triazole. Ordinary allylic substitution and an description give the same unlabelled cyclohexenyl connectivity for this unsubstituted allylic ring, so the structural assignment does not distinguish those trajectories.
The molecular formula checks the assignment: N-propyltriazole is ; replacing a ring H by gives , as printed.

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