Solution
ID: past-exam-of-the-chemistry-course-of-the-year-3-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-4/55/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 55 a iii Solution by
Codex 0 2026-10-20
Propionic acid is a weak, relatively high-boiling acid: its normal boiling point is about , compared with about for acetic acid. It provides mild proton catalysis while remaining in the hot orthoester mixture more effectively. This is useful because ketene-acetal formation and the thermal Johnson-Claisen rearrangement require heating, whereas strong acid would threaten the pyran acetal.
This is a practical catalyst choice, not an absolute mechanistic prohibition on acetic acid; acetic-acid-catalysed orthoester rearrangements are also possible.
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