CIE Jun 2017 v2 Paper 4 Q7

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16 Compounds W, X, Y and Z are isomers of each other with the molecular formula C8H7Cl O. All four isomers contain a benzene ring. Only one of the isomers contains a chiral centre. The results of six tests carried out on W, X, Y and Z are shown in the table. PMT test observations with each isomer add cold AgNO3(aq) white ppt. forms immediately none white ppt. forms very slowly none heat with NaOH(aq), then add dilute HNO3 + AgNO3(aq) add NaOH(aq) + I2(aq) 3 4 warm with Fehlings solution add cold, dilute, acidified KMnO4(aq) add Br2(aq) white ppt. none white ppt. none none pale yellow ppt. none none red ppt. none none none no change no change no change decolourises no change no change no change decolourises and forms white ppt. (a) Use the experimental results in the table above to determine the group(s), in addition to the benzene ring, present in the four isomers W, X, Y and Z. Complete the table below, identifying the group(s) present in each isomer. group(s) in compound[5]UCLES 2017 9701/42/M/J/17<br /> 17 (b) Isomers W, X, Y and Z all have the molecular formula C8H7Cl O. (i) Use the information in (a) to suggest a structure for each of these isomers and draw these in the boxes. PMT (ii) Draw a circle around the chiral centre in one of the above structures. [4] [1] [Total: 10]UCLES 2017 9701/42/M/J/17 [Turn over<br />

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