Name any three functional groups in lawsone.
Describe a reaction, with reagent and conditions, that would let you tell lawsone from compound A. Describe the observations you would make with both compounds.
Suggest a reagent that could be used in the laboratory to turn lawsone into compound A.
Draw the structural formula for the compound obtained when lawsone reacts with $\text{Br}_2(aq)$.
Compound A can be oxidised to lawsone by acidified $\text{K}_2\text{Cr}_2\text{O}_7$. Using the Data Booklet, Calculate the $E^\circ_{\text{cell}}$ for this reaction.
Construct an equation for this reaction, using the molecular formulae of lawsone, $\text{C}_{10}\text{H}_6\text{O}_3$, and compound A, $\text{C}_{10}\text{H}_8\text{O}_3$, in your equation.
A $20.0\ \text{cm}^3$ sample of compound A was acidified and titrated with $0.0500\ \text{mol dm}^{-3}$ $\text{K}_2\text{Cr}_2\text{O}_7$, and $7.50\ \text{cm}^3$ of the $\text{K}_2\text{Cr}_2\text{O}_7$ solution was required to reach the end-point. Calculate $[A]$ in the solution.
Suggest the identity of compound C, then draw its structure in the box above.
A second compound, D, is also formed in the reaction above. D is an isomer of C and has the same functional groups as C, but positioned differently. Suggest one possible structure for D.
Suggest a mechanism for forming D from B and ethanoyl chloride by drawing the relevant structures and curly arrows in the scheme below.