Solution
ID: past-exam-of-the-chemistry-b-course-of-the-university-of-cambridge/2023/paper-1/b1/a/solution
Past exam of the chemistry B course of the University of Cambridge 2023 Paper 1 B1 a Solution by
Codex 0 2026-10-20
Number the ring with chlorine at C1 and the methylsulfonyl group at C4. The new nitro group is at C2, equivalently C6 by the starting ring's symmetry: the product is 1-chloro-2-nitro-4-(methylsulfonyl)benzene. Both substituents favour this site. Although chlorine deactivates the ring inductively, its lone pair donation stabilizes ortho/para Wheland intermediates. The sulfone is strongly electron withdrawing and meta directing; attack ortho or para to it produces especially unfavourable cationic contributors to resonance in chemistry. C2 is ortho to chlorine and meta to sulfone, whereas C3 has the opposite, less favourable relationship.
sulfuric acid protonates nitric acid, followed by loss of water to produce the nitronium ion. A ring pi bond attacks nitrogen, giving the Wheland intermediate with the new C–N bond. deprotonation at the attacked carbon restores aromaticity. This is electrophilic aromatic substitution: the aryl chloride and the sulfone both remain attached. The formula check is . It confirms replacement of one ring hydrogen rather than chlorine, but directing effects, rather than the formula alone, establish the position.
Independently drawn aromatic substitution products and the sites selected by protodebromination
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