Question
Compound $\mathrm{A}, \mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}_{5}$, given a tetraacetate with $\mathrm{Ac}_{2} \mathrm{O}$ and oxidation of $\mathrm{A}$ with $\mathrm{Br}_{2}-\mathrm{H}_{2} \mathrm{O}$ gives an acid, $\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}_{6}$. Reduction of $\mathrm{A}$ with $\mathrm{HI}$ gives isopentane. The possible structure of $\mathrm{A}$ is