Give the systematic IUPAC name of E.
The proton ($^1\text{H}$) NMR spectra for D and E are being compared. They are almost the same. Fig. 7.2 shows the proton ($^1\text{H}$) NMR spectrum of D.
Suggest a suitable solvent for recording the spectrum shown in Fig. 7.2.
The proton ($^1\text{H}$) NMR spectrum of E is recorded twice, once before shaking with $\text{D}_2\text{O}$ and once afterwards. Describe any differences between the two spectra. Explain your answer.
Complete Table 7.1 for D's proton ($^1\text{H}$) NMR spectrum.
Compounds D and E can be told apart using carbon-13 NMR spectroscopy. State the number of peaks in each spectrum. The carbon-13 NMR spectrum of D has ............... peaks. The carbon-13 NMR spectrum of E has ............... peaks.
As shown in Fig. 7.3, compound D can be oxidised to compound F using alkaline $\text{KMnO}_4$ and then dilute acid.
Write an equation for this reaction using the molecular formulae of D and F. This reaction gives F, water and carbon dioxide as products. Use $[O]$ to represent one atom of oxygen from the oxidising agent.
F reacts with excess $\text{SOCl}_2$ to produce compound G. G has molecular formula $\text{C}_8\text{H}_4\text{Cl}_2\text{O}_2$. When G reacts with ethane-1,2-diol, $\text{HOCH}_2\text{CH}_2\text{OH}$, a mixture of products is formed that includes J, with molecular formula $\text{C}_{10}\text{H}_8\text{O}_4$, and K, with molecular formula $\text{C}_{18}\text{H}_{12}\text{Cl}_2\text{O}_6$. Draw the structures of compounds G, J and K in Fig. 7.4.