Past exam of the chemistry course of the year 1 of the natural sciences course of the University of Cambridge / 2025 / 1 / b / i

The assignments are ${\mathrm{H}}_a$: $6.787$ ppm, $1$H, doublet of quartets; ${\mathrm{H}}_b$: $6.496$ ppm, $1$H, doublet of quartets; ${\mathrm{H}}_c$: $4.281$ ppm, $2$H, quartet; ${\mathrm{H}}_d$: $1.331$ ppm, $3$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-$\frac{1}{2}$ fluorine nuclei. The first interaction produces a doublet, and the second a $1:3:3:1$ quartet: eight lines overall, partly interleaved for ${\mathrm{H}}_a$. The two chemical shifts differ because the vinylic sites have different substituents.

The ethoxy $\mathrm{OC}{\mathrm{H}}_2$ protons are deshielded by oxygen and split into a $1:3:3:1$ quartet by the three methyl protons. The methyl protons are split into a $1:2:1$ triplet by the two equivalent methylene protons. The relative NMR signal integrals are $1:1:2:3$.