Hydrocarbon A has the formula C9H12 and absorbs 3 equivalents of H2 to yield B, C9H18, when hydrogenated over a Pd/C catalyst. On treatment of A with aqueous H2SO4 in the presence of mercury(II), two isomeric ketones, C and D, are produced . Oxidation of A with KMnO4 gives a mixture of acetic acid (CH3COOH) and the tricarboxylic acid E. Propose structures for compounds A-D, and write the reactions.

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Hydrocarbon A has the formula C9H12 and absorbs 3 equivalents of H2 to yield B,

C9H18, when hydrogenated over a Pd/C catalyst. On treatment of A with aqueous

H2SO4 in the presence of mercury(II), two isomeric ketones, C and D, are produced .

Oxidation of A with KMnO4 gives a mixture of acetic acid (CH3COOH) and the

tricarboxylic acid E. Propose structures for compounds A-D, and write the reactions.

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