CIE Nov 2016 v3 Paper 4 Q6

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PMT Ibuprofen and paracetamol are pain-relief drugs. 14 OH N H OH ibuprofen paracetamol (a) Ibuprofen and paracetamol both contain the aryl (benzene) functional group. Name the other functional groups present in each molecule. ibuprofenparacetamol[2] (b) Ibuprofen contains a chiral centre and shows stereoisomerism. (i) State what is meant by the term chiral centre.[1] (ii) Draw the two stereoisomers of ibuprofen. [2]UCLES 2016 9701/43/O/N/16<br /> (c) Draw the structures of the organic products when ibuprofen and paracetamol react separately with LiAl H4. 15 PMT product with ibuprofen product with paracetamol [2] (d) A student carried out some reactions with solutions of ibuprofen and paracetamol using reagents D and E and the following results were obtained. ( means a reaction took place.) reagent ibuprofen paracetamol D E (i) Suggest a possible identity for each reagent D and E. DE[2] (ii) Give the structure of the organic product formed when reagent D reacted with ibuprofen. product with ibuprofen [1] (iii) Give the structure of the organic product formed when reagent E reacted with paracetamol. product with paracetamolUCLES 2016 9701/43/O/N/16 [1] [Turn over<br /> (e) One of the steps in the manufacture of ibuprofen is shown. 16 PMT CH3COCl Al Cl 3 (i) Write an equation for the reaction between CH3COCl and Al Cl 3.[1] (ii) Complete the mechanism for the conversion of X into Y. Include all necessary curly arrows, any relevant dipoles and charges. (iii) Name the mechanism in (ii).[1] [Total: 16] [3]UCLES 2016 9701/43/O/N/16<br /> 17 PMT Question 7 starts on the next page.UCLES 2016 9701/43/O/N/16 [Turn over<br />

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