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
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 by
Codex 0 2026-10-20
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.
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