CIE Jun 2013 v3 Paper 4 Q5

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Examiners For Use 10 (a) A series of experiments is carried out in which the reagent shown at the top of the column of the table is mixed, in turn, with each of the reagents at the side. Complete the following table by writing in each box the formula of any gas produced. Write x in the box if no gas is produced. Therst column has been completed as an illustration. OH CO2H OH H2O H2 x x Na KOH(aq) Na2CO3(aq) (b) Compound C is responsible for the pleasant aroma of apples. It can be prepared from phenol by the following 3-step synthesis. [5] OH step step CH3 H3C OH CH3 H3C OH CH3 step CH3 H3C CH3 CH3 CH3 (i) The only by-product of step 1 is HCl. Suggest the reagent that was used to react with phenol to produce compound A.(ii) What type of reaction is occurring in step 2?(iii) What reagents and conditions are required for step 3?(iv) State the reagent and conditions needed to convert C back to B, the reverse of step 3.[5]UCLES 2013 9701/43/M/J/13<br /> Examiners For Use 11 (c) (i) Either compound A or compound B, or both, react with the following reagents. For each reagent draw the structure of the organic product formed with A, and with B. If no reaction occurs, write no reaction in the relevant box. reagent and conditions product with A product with B an excess of Br2(aq) heat with HBr pass vapour over heated Al 2O3 heat with acidi ed K2Cr2O7 (ii) Choose one of the above reactions to enable you to distinguish between A and B. State below the observations you would make with each compound. reagent observation with A observation with B [7] [Total: 17]UCLES 2013 9701/43/M/J/13 [Turn over<br />

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