Question
Match the $^{1}$ H NMR spectroscopic data in the following table to the compounds shown below; the multiplets may consist of overlapping signals. (FIGURE CANNOT COPY)
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Assign structures to compounds with the following $^{1} \mathrm{H}$ NMR spectra: (FIGURE CANNOT COPY)
Match the spectroscopic data in the table to the compounds whose structures are shown below. (FIGURES CAN'T COPY) $$\begin{array}{ll} \text { Compound } & ^{13} \mathrm{C} \text { NMR } \delta / \mathrm{ppm} \\ \hline \mathbf{A} & 25.1,27.1,41.9,211.3 \\ \mathbf{B} & 136.4,187.1 \\ \mathbf{C} & 20.6,178.1 \\ \mathbf{D} & 13.8,22.3,24.9,30.7,47.2,173.8 \\ \mathbf{E} & 162.3 \\ \hline \end{array}$$
(a) Match the following compounds to the correct $^{1}$ H NMR spectroscopic data given in the table. (b) What coupling patterns do you expect to see in the spectrum of compound $\mathbf{B} ?$ (c) Explain why the signal at $\delta 1.15 \mathrm{ppm}$ in the spectrum of $\mathbf{C}$ is a singlet. (FIGURE CANNOT COPY) $$\begin{array}{ll} \text { Compound } & \text { 1 H NMR } \delta / \text { ppm (relative integral) } \\ \text { A } & 2.69(4 \mathrm{H}), 2.43(6 \mathrm{H}), 1.24(2 \mathrm{H}) \\ \text { B } & 2.30(2 \mathrm{H}), 2.22(6 \mathrm{H}), 1.06(3 \mathrm{H}) \\ \text { C } & 1.41(2 \mathrm{H}), 1.15(9 \mathrm{H}) \\ \hline \end{array}$$
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