Hydrocarbon A, C10H14 absorbs 3 equiv. of hydrogen to give B, C10H20 when hydrogenated over a Pd/C catalyst. Treatment of A with aqueous H2SO4 and Hg(II) gives a single ketone, C, C10H16O. Oxidation of A with KMnO4 gives CO2 and the tricarboxylic acid D shown below. Propose a structure for A.
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