Solution

ID: past-exam-of-the-chemistry-a-course-of-the-university-of-cambridge/2024/paper-2/a7/b/ii/solution

The large negative activation entropy is consistent with a strongly organized bimolecular cycloaddition. Two separately translating and rotating molecules must approach with a restricted orientation to form a compact ring-forming transition state. Losing relative positional and orientational freedom lowers entropy.
Internal conformational restrictions and solvent rearrangement can contribute too. In a nonpolar solvent, a simple association picture is more plausible than assigning the whole effect to strong ionic solvation, but the numerical value is not a direct count of molecular orientations alone.

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