A certain saturated hydrocarbon A is transformed by a catalytic oxidation partly into a secondary al — Physical Chemistry — Thermodynamics Chemistry Question
Transformation of a Saturated Hydrocarbon
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.
Write the structural formulas of compounds A, B, C, D, and E.
Model Answer
In general: oxidationketone carboxylic acid→
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:
D:
oxidation
cyclohexanone adipic acid
A: cyclohexane
C: cyclohexanone
B: cyclohexanol
acetic anhydride HOOC - (CH2)n - COOH if n = 2, 3
if n > 3
CO2 + H2O
Compound E: cyclopentanone