Question

Hydrocarbon A has the formula C9H12 and absorbs 8 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 (CH3CO2H) and the tricarboxylic acid E.

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

Hydrocarbon A has the formula C3H12 and absorbs 8 equivalents of H2 to yield B, (C,H18), 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 (CH3CO2H) and the tricarboxylic acid E. Propose structures for compounds A-D, and write the reactions. CH2CO2H HO2CCH2CHCH2CO2H E