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In the boxes, draw the structures of compounds $A$, $B$, $C$, $D$, $E$ and $F$.
Chemistry 9701 · AS & A Level · Organic synthesis
Organic synthesis — practice question
The $^{13}\text{C}$ NMR spectrum of compound $A$, $\text{C}_8\text{H}_8\text{O}_2$, shows six peaks. Compound $A$ is treated with excess bromine water to produce compound $B$, $\text{C}_8\text{H}_6\text{Br}_2\text{O}_2$. When compound $A$ is reacted with alkaline aqueous iodine, a yellow precipitate $C$ and compound $D$ are formed. Compound $D$ then reacts with $\text{PCl}_5$ to give compound $E$, $\text{C}_7\text{H}_5\text{O}_2\text{Cl}$. Compound $E$ reacts with propan-2-ol to form compound $F$.