Hydrocarbon A, C10H14 absorbs 3 equiv. of hydrogen to give B, C10H20 when hydrogenated over a Pd/C catalyst. Treatment of A with aqueous H,SO4 and Hg(II) gives a single ketone, C, C1,H160. Oxidation of A with KMNO4 gives CO2 and the tricarboxylic acid D shown below. Propose a structure for A. ÇO2H „CO2H A CO2 HO;C H3C CH3 Oxidation products

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I cannot figure out structure A?

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.
ÇO2H
.CO2H
А
CO2
HO2C
CH3
H3C
D
Oxidation products
Transcribed Image Text: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. ÇO2H .CO2H А CO2 HO2C CH3 H3C D Oxidation products
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