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A certain saturated hydrocarbon A is transformed by a catalytic oxidation partly into a secondary alcohol B,and partly into a ketone C.The ketone when oxidised with nitric acid in the presence of catalyst yields a compound D with a formula of C6H10O4.From compound D when heated in the presence of acetic anhydride,a ketone E is formed, its formation being accompanied by evolution of CO2 and H2O. Compounds E and C have similar structures but compound E contains one methylene group less than ketone C. Compound D is one of the starting materials in the production of an important polycondensation synthetic fibre. Problem: 

Write the structural formulas of compounds A, B, C, D, and E. 

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C6H10O4 = C4H8(COOH)2 = HOOC-(CH2)4-COOH 

Product D is adipic acid which is a basic material in the production of nylon. 

Compound C is cyclohexanone, because: 

Compound E: cyclopentanone

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