CIE Mar 2017 v2 Paper 4 Q7

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The compound Advantame is a sweetener that tastes approximately 25 000 times sweeter than sucrose. 16 PMT RO HO N H H N OH Advantame CH3 (a) Advantame is optically active. On the diagram of Advantame, circle all the chiral carbon atoms. [1] (b) The decomposition of Advantame produces three molecules, J, K and L. The RO group in Advantame is unreactive. RO HO H N OH OH H2N OH O K (i) Suggest possible reagents and conditions for this decomposition.[1] (ii) Name the type of reaction occurring.[1] (iii) Draw the structure of L in the box above. [1]UCLES 2017 9701/42/F/M/17<br /> PMT 17 (c) (i) Aqueous bromine was added dropwise to a solution of J until the bromine was in excess. State what you would observe.[1] (ii) J has the molecular formula C14H19O6N. Use this formula to write an equation for the reaction of excess aqueous sodium hydroxide with one mole of J.[2] (d) (i) State what you would observe when an excess of aqueous bromine is added to a solution of K.[1] (ii) K can be polymerised. Draw the structure of the polymer showing two repeat units. The linkage between the monomer units should be fully displayed. [2]UCLES 2017 9701/42/F/M/17 [Turn over<br /> 18 (e) Use the Data Booklet to help you answer this question. The carbon-13 NMR spectrum of K was recorded. PMT OH H2N (i) State how many different carbon environments are present in K.[1] (ii) The chemical shifts, , due to two of the carbon atoms x and y present in K are given in the table. carbon atom x y/ ppm 130 170 On the structure of K, circle and label two carbon atoms which could correspond to x and y. [1] [Total: 12]UCLES 2017 9701/42/F/M/17<br /> 19 PMT Question 8 starts on the next page.UCLES 2017 9701/42/F/M/17 [Turn over<br />

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