A friend of yours, who is a graduate student attempting to establish the structure of a chemical species from field clover, isolated an alcohol that was found to have an optical rotation of +49.5°. Chemical analysis gave a molecular formula of C5H10O. It was also observed that this alcohol readily decolorized Br2–CH2Cl2 solution. On this basis, the alcohol was subjected to catalytic hydrogenation and it was found to absorb 1 mol equivalent of hydrogen gas. The product of the reduction gave a positive ceric nitrate test, indicating that it, too, was an alcohol. However, the reduced compound was optically inactive. Your friend has come to you for assistance in determining the structures of the two alcohols. What do you believe the structures are?
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