Explain treatment of a with aqueous h2so4

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Hydrocarbon A, C10H14 absorbs 4 equiv. of hydrogen to give B, C10H22 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 keto carboxylic acid D shown below. Propose a structure for A.

Reference no: EM13337798

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