Solution

ID: past-exam-of-the-chemistry-b-course-of-the-university-of-cambridge/2025/paper-1/b4/b/iii/solution

Use the upper-ring chair placing or axial. The aryl ester substituent on that carbon is then equatorial. Use a lower-ring chair placing or axial, with the attached side chain equatorial. The spiro configuration distinguishes the two structures: in A, the lower-ring oxygen bond is axial with respect to the upper ring, while the upper-ring oxygen bond is equatorial with respect to the lower ring. In B, those roles reverse.
Thus the oxygen placements at the shared spiro carbon are axial/equatorial for A and equatorial/axial for B. Side-chain conformations are unnecessary, but changing the lower chair without tracking its substituent positions would change this conclusion.
Figure 1.
Chair assignments for the two spiroacetals: axial reporter hydrogens and one axial exocyclic oxygen in each isomer
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