Chapter 12, Problem 12.18P

Draw the products formed when both cis- and trans-but-2-ene are treated with ${\text{OsO}}_{\text{4}}$,

followed by hydrolysis with ${\text{NaHSO}}_{\text{3}}+{\text{H}}_{\text{2}}\text{O}$. Explain how these reactions illustrate that

syn dihydroxylation is stereospecific.