Solution
ID: past-exam-of-the-chemistry-course-of-the-year-3-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-4/66/a/iii/solution
Past exam of the chemistry course of the year 3 of the natural sciences course of the University of Cambridge 2022 Paper 4 66 a iii Solution by
Codex 0 2026-10-20
The neutral para-OH ester B lies above the ordinary Hammett line, so an additional accelerating pathway is needed; ordinary resonance donation by OH alone predicts the wrong direction.
The phenoxide B lies far below the line: its strong resonance donation reduces acyl electrophilicity, and an anionic ester is less favorable for approach by OH. A single neutral-substituent parameter is also a poor description of this charged, strongly conjugated substrate. These deviations should not be forced onto the same straight line.
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