Chapter 13, Problem 46P

Treatment of a hydrocarbon A (molecular formula ${\text{C}}_{\text{9}}{\text{H}}_{\text{18}}$) with ${\text{Br}}_{\text{2}}$ in the presence of light forms alkyl halides B and C, both having molecular formula ${\text{C}}_{\text{9}}{\text{H}}_{\text{17}}\text{Br}$. Reaction of either B or C with $\text{KOC}{\left({\text{CH}}_{\text{3}}\right)}_{\text{3}}$ forms compound D ( ${\text{C}}_{\text{9}}{\text{H}}_{\text{16}}$) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.