Solution

ID: past-exam-of-the-chemistry-b-course-of-the-university-of-cambridge/2025/paper-1/b3/c/i/solution

At 400 MHz, a separation in ppm corresponds to Hz. The two multiplets near 5.10 and 4.47 ppm each have a quoted separation of 0.02 ppm, giving Hz. The multiplets near 4.625 and 3.865 ppm each have separation 0.01 ppm, giving Hz. These are approximate values from the rounded peak labels.
The fused unsaturated/aromatic framework restricts the five-membered ring, as in the comparison in (a). Assign the larger coupling to cis and the smaller to trans. Matching equal couplings and integrals pairs the 5.10/4.47 signals with one another, and the 4.625/3.865 signals with one another. The integral ratio is
With an achiral substrate and achiral catalytic environment, each diastereomer is expected as a racemic enantiomeric pair: cis and trans . The reported spectrum requires both diastereomers; the reagent label alone cannot override that evidence. Their ratio does not establish whether the selectivity arose in the initial surface addition or after product epimerization.

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