OCR A Jan 2010 Paper 4 Q5

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5 Aspirin and paracetamol are commonly available painkillers. 12 COOH H3C H3C OH aspirin paracetamol Aspirin and paracetamol can be prepared using ethanoic anhydride, (CH3CO)2O. Some examples of the reactions of ethanoic anhydride are shown below. reaction 1 reaction 2 reaction 3 (CH3CO)2O + CH3OH (CH3CO)2O + CH3NH2 (CH3CO)2O + C6H5OH CH3COOCH3 + CH3COOH CH3CONHCH3+ CH3COOH CH3COOC6H5 + CH3COOH (a) Draw the structure of a compound that could react with ethanoic anhydride to form aspirin. [1]OCR 2010<br />
 (b) Ethanoic anhydride can react with 4-aminophenol to produce paracetamol. (i) Write an equation, showing structural formulae, for this formation of paracetamol. 13 (ii) An impurity with molecular formula C10H11NO3 is also formed. Draw the structure of this impurity. [2] [1] (iii) Explain why it is necessary for pharmaceutical companies to ensure that drugs and medicines are pure.[1] (c) Name the functional groups in aspirin and in paracetamol. aspirinparacetamol[2]OCR 2010 Turn over<br />
 (d) A student carried out some reactions with samples of aspirin and paracetamol in the laboratory. Their structures are repeated below. 14 COOH H3C H3C OH aspirin paracetamol The student tried to react each of the reagents A, B and C with aspirin and paracetamol.Reagent A reacted with aspirin and with paracetamol.Reagent B reacted only with aspirin.Reagent C reacted only with paracetamol. Suggest possible identities of reagents A, B and C and the organic products that would be formed. (i) Reagent A:Organic product with aspirin: Organic product with paracetamol: [3]OCR 2010<br />
 (ii) Reagent B:15 Organic product with aspirin: (iii) Reagent C:Organic product with paracetamol: [2] [2] [Total: 14] END OF QUESTION PAPEROCR 2010<br />

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