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/b/solution

The kink indicates that two pathways with different leaving-group sensitivities compete: one dominates for good leaving groups and another for poorer ones. A single straight-line free-energy relationship is insufficient. The additional hydroxide-order information can be accommodated by rapid phenol deprotonation,
Two rates are then possible. A route with one hydroxide equivalent in its overall kinetic dependence contributes . Attack of a further hydroxide on phenoxide ester contributes
Thus . The third-order term need not involve a simultaneous collision of three molecules: sequential acid-base equilibration followed by bimolecular attack produces it.

New to topics? Read the docs here!