Challenging Organic Question (O Level)
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Challenging Organic Question (O Level)A has the following composition by mass. C : 40.00%, H : 6.67%, O : 53.33%. 3.6g of A reacts completely with 20.00 c m3 of 1.00 mol d m−3 aqueous N a2CO3 in the molar ratio of 2 : 1, liberating an unknown gas B. A also reacts with aqueous NaOH to form C. When acidified potassium dichromate (VI) is added to A, the orange solution decolourises to form a green solution, forming D in the process. D reacts with NaHCO3 in a 1 : 2 molar ratio. (a) Compute the empirical formula for A, the M r of A and hence state the molecular formula of A.[3 or 4](b) Suggest a test to identify gas B. [1](c) Based on the above information, suggest the full structural formulas for A, C and D. Explain the reactions that occur.[5 or 6](d) Write balanced equations for:(i) A to C(ii) A to D. [2](e) A can form a sweet smelling liquid E, C3H 4O2, when heated with someconcentrated H 2SO 4.(i) Suggest a formula for E.(ii) In this process, another compound, F, a polymer, was isolated. Suggest a structure for F, showing 2 repeat units.[3]