Solution
ID: past-exam-of-the-chemistry-course-of-the-year-4-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-2/section-i/35/c/ii/solution
Past exam of the chemistry course of the year 4 of the natural sciences course of the University of Cambridge 2022 Paper 2 Section I 35 c ii Solution by
Codex 0 2026-10-20
Sulfuryl chloride converts the aryl thiol into an electrophilic sulfur reagent, conveniently represented as after chlorination and dehydrogenation. Triethylamine traps the generated acid. The pyrrole's two positions are already occupied; its less deactivated remaining carbon, C4, attacks electrophilic sulfur, displacing chloride. Loss of the C4 proton restores the aromatic ring and gives the C4 arylthio-substituted pyrrole.
The net new bond is C(pyrrole)–S(aryl). Sulfur is retained from the thiol and becomes a thioether; the transformation is not sulfonylation by transfer of sulfuryl chloride's SO group. Possible disulfide formation during thiol chlorination does not change the electrophilic-sulfenylation logic of the final ring substitution.
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