Problem

Compound A(C5H8) is not optically active and cannot be separated into enantiomers. It re...

Compound A(C5H8) 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(C5H8Br2). When Compound A is treated with H2 in the presence of a transition metal catalyst, it is converted to compound C(C5H10). When treated with HCl, compound A is converted to compound D(C5H9Cl). 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.

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