Chapter 14, Problem 37P

15-41 Compound A(C₅H_h, is not optically active and cannot be separated into enantiomers. It reacts with bromine in carbon tetrachloride to discharge the purple color of bromine and form Compound B( C.FL Br,). When Compound A is treated with H., in the presence of a transition metal catalyst, it is converted to compound C(C₅H₁₀). When treated with HC1, compound A is converted to compound DtC.HyCl). Given this information, propose structural formulas for compounds A B, C, and D. Hint: There are at least three possibilities for Compound A and, in turn, three possibilities for Compounds B. C, and D.