Solution
ID: past-exam-of-the-chemistry-course-of-the-year-3-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-4/67/a/solution
Past exam of the chemistry course of the year 3 of the natural sciences course of the University of Cambridge 2022 Paper 4 67 a Solution by
Codex 0 2026-10-20
Protonation converts OH into a water leaving group; ionization then gives the diarylmethyl cation. The labeled C-H/D bond is retained, so is a normal alpha-secondary kinetic isotope effect, not a primary C-H cleavage effect.
At the labeled carbon, tetrahedral geometry becomes approximately trigonal planar. The associated change in bending vibrations and zero-point energies favors the H isotopologue in a substantially carbocation-like transition state. The two anisyl rings stabilize that cation and make this ionization pathway plausible.
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