9701_w09_qp_42
A paper of Chemistry, 9701
Questions:
9
Year:
2009
Paper:
4
Variant:
2

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For Examiner’s Use All the carbon atoms in benzene lie in the same plane. This means that they are coplanar, but this is not the case with cyclohexane. benzene cyclohexane By rotating the molecule around its several C–C bonds, all the carbon atoms in butane can be made to lie in the same plane, but this is not the case with methylpropane. CH2 CH3 CH2 H3C CH3 H3C H3C H butane methylpropane By considering the 3-dimensional geometry of the following five molecules, and allowing rotations around C–C bonds, decide whether or not the carbon atoms in each molecule can be arranged in a coplanar fashion. Then place a tick in the appropriate column in the table below. A B C D E CH3 CH3 CH3CH(OH)CO2H CH3 H2N O O C C H3C H3C O C NO2 H C compound all carbon atoms can be coplanar not all carbon atoms can be coplanar A B C D E For Examiner’s Use Methylbenzene can react with chlorine under different conditions to give the monochloro derivatives F and G. F G CH3 CH3 I II CH2Cl Cl Suggest reagents and conditions for each reaction. reaction I reaction II For Examiner’s Use Benzyl benzoate is a constituent of many perfumery products, and has also been used in the treatment of the skin condition known as scabies. It can be made from methylbenzene by the following route, which uses one of the chlorination reactions from . CO2H CH2OH CH3 III IV V VI H C CH2 O O benzyl benzoate Draw the structural formula of the intermediate H in the box above. For Examiner’s Use Suggest reagents and conditions for each reaction. reaction Ill reaction V reaction VI State the type of reaction occurring during reaction Ill, reaction V.
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For Examiner’s Use The residues from organohalogen pesticides are known to be a major cause of the decline in numbers of different birds of prey in many countries. These residues are concentrated in birds at the top of food chains. Analysis of the bodies of birds of prey show that the pesticide residues accumulate in the fatty tissues of the birds. This is because of the high partition coefficient between the fat in the tissues and water found in blood. Explain what is meant by the term partition coefficient. A particular pesticide has a partition coefficient of 8.0 between the solvent hexane and water. If a 25 cm3 sample of water containing 0.0050 g of the pesticide is shaken with a 25 cm3 sample of hexane, calculate the mass of pesticide that will dissolve in the hexane layer. Compounds used as pesticides may contain bromine or chlorine. What would be the difference in the ratio of the M: M+2 peaks if the pesticide contained one chlorine rather than one bromine atom? If a given pesticide contains two chlorine atoms per molecule, deduce the relative heights of the M, M+2 and M+4 peaks. For Examiner’s Use The following graph shows the occurrence of pesticide residues in the eggs of fish-eating birds of prey upstream and downstream of a paper mill at Castlegar on the Columbia River in Canada. Columbia River Basin downstream of Castlegar TEQs parts per trillion upstream of Castlegar Furan 2378TCDF Dioxin 2378TCDD Other Dioxins / Furans PCBs PCBs, the dioxin 2378TCDD, and the furan 2378TCDF all come from chemicals containing chlorine. Suggest which compounds are present directly as a result of the paper mill. By studying the data for 1994, suggest which chemicalcome from sources other than the paper mill. Compare the downstream data for 1994 with that for 1997. Suggest what might be responsible for the change. A molecule of 2378TCDD contains four chlorine atoms. How many molecular ion peaks would this compound show in its mass spectrum?
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