Solution

ID: past-exam-of-the-chemistry-course-of-the-year-1-of-the-natural-sciences-course-of-the-university-of-cambridge/2024/paper-1/1/c/i/solution

Use the proton labels in the original drawing below. Let denote the three methyl hydrogens, the crotonyl beta-CH, the crotonyl alpha-CH, the O-bound vinyl CH, and the terminal vinyl hydrogens trans and cis to , respectively.
The integrals sum to eight hydrogens. Multiplet centres give the chemical shifts; a peak label at one edge of a multiplet is not its centre. The terminal vinyl hydrogens are chemically nonequivalent because one is cis and the other trans to the O-bound vinyl hydrogen. Each crotonyl CH couples to the other and to the methyl group; the resolved long-range interaction makes the methyl a doublet of doublets rather than a simple doublet.
Figure 1.
Original structure showing all eight hydrogens, their environments and calculated NMR coupling constants
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