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In the boxes, sketch the structures of compounds $A$, $B$, $C$, $D$, $E$ and $F$.
Chemistry 9701 · AS & A Level · States of matter
States of matter — practice question
The $^{13}\text{C}$ carbon-13 NMR spectrum for compound $A$, $\text{C}_8\text{H}_8\text{O}_2$, shows six peaks. When compound $A$ is treated with an excess of bromine water, compound $B$ is produced, with formula $\text{C}_8\text{H}_6\text{Br}_2\text{O}_2$. Compound $A$ also reacts with alkaline aqueous iodine to give a yellow precipitate $C$ together with compound $D$. On reaction with $\text{PCl}_5$, compound $D$ forms compound $E$, $\text{C}_7\text{H}_5\text{O}_2\text{Cl}$. Compound $E$ then reacts with propan-2-ol to produce compound $F$.