Solution

ID: past-exam-of-the-chemistry-course-of-the-year-1-of-the-natural-sciences-course-of-the-university-of-cambridge/2025/1/b/i/solution

The assignments are : ppm, H, doublet of quartets; : ppm, H, doublet of quartets; : ppm, H, quartet; : ppm, H, triplet. The chemical shift of a multiplet is its centre, rather than its most downfield line.
Each vinylic proton has scalar spin-spin coupling to the other vinylic proton and to three equivalent spin- fluorine nuclei. The first interaction produces a doublet, and the second a quartet: eight lines overall, partly interleaved for . The two chemical shifts differ because the vinylic sites have different substituents.
The ethoxy protons are deshielded by oxygen and split into a quartet by the three methyl protons. The methyl protons are split into a triplet by the two equivalent methylene protons. The relative NMR signal integrals are .

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