Chapter 12, Problem 12.54P

An unknown compound A of molecular formula ${\text{C}}_{\text{10}}{\text{H}}_{\text{18}}\text{O}$ reacts with ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ to form two compounds (B and C) of molecular formula ${\text{C}}_{\text{10}}{\text{H}}_{\text{16}}$. B and C both react with ${\text{H}}_{\text{2}}$ in presence of $\text{Pd}$ catalyst to form decalin. Ozonolysis of B forms D, and ozonolysis of C forms a diketone E of molecular formula ${\text{C}}_{\text{10}}{\text{H}}_{\text{16}}{\text{O}}_2$. Identify the structures of compounds A, B, C, and E.