9701_s09_qp_4
A paper of Chemistry, 9701
Questions:
9
Year:
2009
Paper:
4
Variant:
0

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For Examiner’s Use In the following boxes draw the structural formulae of three alcohols having straight (i.e. unbranched) chains, with the molecular formula C5H12O. A B C Use the letters A, B or C as appropriate when answering the following questions. Each letter may be used once, more than once or not at all. Which of the alcohols are chiral? Which of these alcohols react with alkaline aqueous iodine? Describe the observation you would make during this reaction. Draw the structural formulae of the products of this reaction. Draw the structural formula of the product obtained when each of the alcohols A, B and C is heated with an excess of acidified K2Cr2O7. A B C For Examiner’s Use One of the many suggestions for converting biomass into liquid fuel for motor transport is the pyrolysis (i.e. heating in the absence of air) of cellulose waste, followed by the synthesis of alkanes. In the first reaction, cellulose, (C6H10O5)n, is converted into a mixture of carbon monoxide and hydrogen. Some carbon is also produced. Complete and balance the equation for this reaction. (C6H10O5)n ————————— + ————————— + ————————— The second reaction involves the combination of CO and H2 to produce alkanes such as heptane. 7CO + 15H2 C7H16 + 7H2O heptane Using the value of 1080 kJ mol−1 as the value for the CO bond energy in CO, and other relevant bond energies from the Data Booklet, calculate the ∆H for this reaction. ∆H = kJ mol−1
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For Examiner’s Use A large number of organic compounds are soluble in both water and non-aqueous solvents such as hexane. If such a compound is shaken with a mixture of water and the non-aqueous solvent, it will dissolve in both solvents depending on the solubility in each. State what is meant by the term partition coefficient. When 100 cm3 of an aqueous solution containing 0.50 g of an organic compound X was shaken with 20 cm3 of hexane, it was found that 0.40 g of X was extracted into the hexane. Calculate the partition coefficient of X between hexane and water. If two 10 cm3 portions of hexane were used instead of a single 20 cm3 portion, calculate the total amount of X extracted and compare this with the amount extracted using one 20 cm3 portion. For Examiner’s Use PCBs are highly toxic compounds released into the atmosphere when some plastics are burned at insufficiently high temperatures. In recent years PCB residues have been found in the breast milk of Inuit mothers in northern Canada. Foods, such as oily fish, seal and whale meat, which are high in fat, form an important part of the Inuit diet. Suggest why berries and drinking water are not contaminated by PCBs in the same way that oily fish, seal and whale meat are. Based on the information provided, what can you say about the partition coefficient between fat and water for PCB residues? For Examiner’s Use The diagram shows the result of two-way paper chromatography. X starting point solvent 1 solvent How many spots were there after the first solvent had been used? Circle the spot that moved very little in solvent 2, but moved a greater distance in solvent 1. Draw a square around the spot that could be separated from the rest by using only solvent 1.
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For Examiner’s Use Spider silk is a natural polymer which has an exceptional strength for its weight. Kevlar is a man-made polymer designed to have similar properties. It has a wide variety of uses from sporting equipment to bullet-proof vests. C O H N H N O C N H C O O C N H O C Kevlar In Kevlar, the polymer strands line up to form strong sheets with bonds between the strands. On the diagram above, draw part of a second polymer chain showing how bonds could be formed between the chains. Suggest what type of bonds these are. Draw two possible monomer molecules for making the polymer Kevlar. The transport of oil by sea has resulted in a number of oil spills in recent years. As well as a waste of a valuable resource, these have caused major environmental problems. Traditional sorbent materials absorb water and sink. Researchers have developed new sorbent materials to help collect the spilled oil. The sorbent consists of a material called ‘hydrophobic aerogels’. This is a network of silicon(oxide with some of the silicon atoms attached to fluorine-containing groups. —O—Si—CH2—CF3 The introduction of these fluorine-containing groups allows the oil to be absorbed but not the water. Tests show that these materials can absorb more than 200 times their mass of oil without sinking. Suggest what the word hydrophobic means. Suggest why the fluorine-containing groups allow oil to pass through but not water molecules. Suggest another important fluorine-containing polymer that repels water-containing materials.