Past exam of the chemistry course of the year 1 of the natural sciences course of the University of Cambridge / 2022 / Paper 1 / 1 / a / iii

Write the proton-labelled structure as $\mathrm{C}{\mathrm{H}}_3^{\mathrm{a}}\mathrm{C}(=\mathrm{O})\mathrm{C}{\mathrm{H}}^{\mathrm{b}}(\mathrm{Cl})\mathrm{C}{\mathrm{H}}_3^{\mathrm{c}}$. The assignments areThe NMR quartet is centred at $(4.371+4.302)/2=4.3365$ ppm; each adjacent line differs by $0.023$ ppm. The NMR doublet has the same spacing, $1.618-1.595=0.023$ ppm. At 300 MHz,Three equivalent methyl protons split $b$ into a $1:3:3:1$ NMR quartet; the single methine proton splits $c$ into a $1:1$ NMR doublet. No resolved long-range scalar coupling splits the acetyl methyl, giving its NMR singlet. The integrals total seven protons.