Solution
ID: past-exam-of-the-mphil-in-micro-and-nanotechnology-enterprise-course-of-the-university-of-cambridge/2021/paper-1/5/iii/solution
Past exam of the MPhil in micro- and nanotechnology enterprise course of the University of Cambridge 2021 Paper 1 5 iii Solution by
Codex 0 2026-10-20
Each imidazole already has one nitrogen substituted. Its remaining pyridine-like nitrogen attacks a benzylic carbon bearing chlorine in an reaction, expelling chloride and producing an imidazolium center. Repetition at the other end closes the ring. The expected product is therefore a dicationic bis-imidazolium macrocycle, in which two meta-xylylene bridges connect the two imidazolium rings. Both nitrogens of each imidazolium are alkylated; the aryl rings remain intact.
A compact way to specify its connectivity is to traverse the ring:Here each indicated imidazolium connects its two substituents through its two different ring nitrogen atoms, rather than through a single nitrogen.
chloride acts as an anion template: association with the positively charged intermediates and the inward-facing imidazolium CH donors brings the reacting ends together, favoring cyclization over intermolecular oligomerization. Tetrabutylammonium is a spectator counterion, not a covalent part of the product. The two substitutions produce two chloride counterions for the dication; template chloride can also occupy the cavity, with the remaining ions in solution. The schematic below specifies connectivity and charge without reproducing the source drawing.
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