A water-insoluble hydrocarbon A decolorizes a solution of Br₂ in CH₂Cl₂. The base peak in the EI mass spectrum of A occurs at m/z = 67. The proton NMR of A is complex, but integration shows that about 30% of the protons have chemical shifts in the δ1.8–2.2 region of the spectrum.

Treatment of A successively with OsO₄, then periodic acid, and finally with Ag₂O, gives a single dicarboxylic acid B that can be resolved into enantiomers. Neutralization of a solution containing 100 mg of B requires 13.7 mL of 0.1 M NaOH solution. Compound B, when treated with POCl₃, forms a cyclic anhydride. Give the structures of A and B.