Question
An unknown hydrocarbon A with the formula C₆H₁₂ reacts with 1 molar equivalent of H₂ over a palladium catalyst. Hydrocarbon A also reacts with OsO₄ to give diol B. When oxidized with KMnO₄ in acidic solution, A gives two fragments. One fragment is propanoic acid, CH₃CH₂CO₂H, and the other fragment is ketone C. What are the structures of A, B, and C? Write all reactions.
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Evidence boundary
This answer identifies A, B, C and the hydrogenation product from the formula and the three reactions given in the prompt. It does not report measured yields, reaction rates or stereochemical ratios, and it does not treat alternative structures that the stated data exclude.