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/i/solution

A is 1-propyl-1,2,4-triazole, with propyl on the nitrogen that is adjacent to one N and one C in the triazole ring, rather than on the nitrogen between the two carbon atoms.
DBU removes the ring NH proton, producing a resonance-stabilized triazolide anion. Nitrogen attacks the primary bromide carbon by an SN2 reaction, displacing bromide and giving the N-propyl product. Alkylation at the equivalent tautomer-related N1/N2 positions gives the same constitutional product, while N4 alkylation would give a different isomer. Charge distribution in the triazolide and the accessibility of its nitrogen lone pairs favor the N1 product under the stated conditions. This is kinetic regioselectivity, not an assertion that the unalkylated tautomer has a permanently localized negative charge.

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