UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level

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1 UNIVERSITY O MRIGE INTERNTIONL EXMINTIONS General ertificate of Education dvanced Subsidiary Level and dvanced Level * * EMISTRY 971/1 Paper 1 Multiple hoice May/June 28 dditional Materials: RE TESE INSTRUTIONS IRST Multiple hoice nswer Sheet Soft lean Eraser Soft pencil (type or is recommended) ata ooklet 1 hour Write in soft pencil. o not use staples, paper clips, highlighters, glue or ion fluid. Write your name, entre number and candidate number on the nswer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. nswer all questions. or each question there are four possible answers,, and. hoose the one you consider and record your choice in soft pencil on the separate nswer Sheet. Read the instructions on the nswer Sheet very carefully. Each answer will score one mark. mark will not be deducted for a wrong answer. ny rough working should be done in this booklet. This document consists of 16 printed pages. I8 6_971_1/2RP ULES 28 [Turn over

2 2 Section or each question there are four possible answers,,,, and. hoose the one you consider to be. 1 In the asic Oxygen steel-making process the P 4 O 1 impurity is removed by reacting it with calcium oxide. The only product of this reaction is the salt calcium phosphate, a 3 (PO 4 ) 2. In this reaction, how many moles of calcium oxide react with one mole of P 4 O 1? Use of the ata ooklet is relevant to this question. typical solid fertiliser for use with household plants and shrubs contains the elements N, P, and K in the ratio of 15 g : 3 g :15 g per 1 g of fertiliser. The recommended usage of fertiliser is 14 g of fertiliser per 5 dm 3 of water. What is the concentration of nitrogen atoms in this solution?.3 mol dm 3.5 mol dm 3.42 mol dm 3.75 mol dm Skin cancer can be treated using a radioactive isotope of phosphorus, 15 P. compound containing the phosphide ion 32 P 3 15, wrapped in a plastic sheet, is strapped to the affected area. What is the composition of the phosphide ion, P? protons neutrons electrons ULES /1/M/J/8

3 4 When barium metal burns in oxygen, the ionic compound barium peroxide, ao 2, is formed. 3 Which dot-and-cross diagram represents the electronic structure of the peroxide anion in ao 2? key electron from first oxygen atom electron from second oxygen atom electron from barium atom 5 In this question, the methyl group, 3, is represented by. Trimethylamine, 3 N, reacts with boron trifluoride, 3, to form a compound of formula 3 N. 3. ow may this reaction be written in terms of the shapes of the reactants and products? + N N N + N + N N N + N ULES /1/M/J/8 [Turn over

4 4 6 The density of ice is 1. g cm 3. What is the volume of steam produced when 1. cm 3 of ice is heated to 323 (596 K) at a pressure of one atmosphere (11 kpa)? [1 mol of a gas occupies 24. dm 3 at 25 (298 K) and one atmosphere.].267 dm dm dm dm 3 7 Which pair of elements have bonds of the same type between their atoms in the solid state? aluminium and phosphorus chlorine and argon magnesium and silicon sulphur and chlorine 8 Which diagram ly describes the behaviour of a fixed mass of an ideal gas? (T is measured in K.) constant T constant T constant T constant p p pv pv V V p V T 9 or which equation does the enthalpy change correspond to the enthalpy change of atomisation of iodine? ½ I 2 (s) I(s) ½ I 2 (s) I(g) I 2 (g) 2I(g) I 2 (s) 2I(g) ULES /1/M/J/8

5 5 1 Titanium occurs naturally as the mineral rutile, TiO 2. One possible method of extraction of titanium is to reduce the rutile by heating with carbon. TiO 2 (s) + 2(s) Ti(s) + 2O(g) The standard enthalpy changes of formation of TiO 2 (s) and O(g) are 94 kj mol 1 11 kj mol 1 respectively. and What is the standard enthalpy change of this reaction? 83 kj mol 1 72 kj mol kj mol kj mol 1 11 or the reaction W(aq) + 2X(aq) 2Y(aq) + 3Z(aq) what are the units for the equilibrium constant K c? mol dm 3 mol 2 dm 6 mol 1 dm 3 mol 2 dm 6 ULES /1/M/J/8 [Turn over

6 6 12 The molecular energy distribution curve represents the variation in energy of the molecules of a gas at room temperature. proportion of molecules energy Which curve applies for the same gas at a lower temperature? proportion of molecules proportion of molecules energy energy proportion of molecules proportion of molecules energy energy 13 In an experiment,.1 g samples of Na 2 O, MgO, P 4 O 1 and SO 2 are added to separate 1 cm 3 volumes of water. or which oxide is the resulting mixture most alkaline? Na 2 O MgO P 4 O 1 SO 2 ULES /1/M/J/8

7 14 Which element is expected to show the greatest tendency to form some covalent compounds? 7 aluminium calcium magnesium sodium 15 Use of the ata ooklet is relevant to this question. The combustion of fossil fuels is a major source of increasing atmospheric carbon dioxide, with a consequential rise in global warming. nother significant contribution to carbon dioxide levels comes from the thermal decomposition of limestone, in the manufacture of cement and of lime for agricultural purposes. ement works roast 1 million tonnes of limestone per year and a further 2 million tonnes is roasted in kilns to make lime. What is the total annual mass output of carbon dioxide (in million tonnes) from these two processes? Properties of chlorine, iodine and their compounds are compared. Property Q for chlorine is smaller than for iodine. What is property Q? oxidising ability of the element solubility of the silver halide in N 3 (aq) strength of van der Waals forces between the molecules of the element thermal stability of the hydrogen halide 17 Which reagent, when mixed and heated with ammonium sulphate, liberates ammonia? aqueous bromine dilute hydrochloric acid limewater acidified potassium dichromate(vi) ULES /1/M/J/8 [Turn over

8 8 18 The diagram represents the aber process for the manufacture of ammonia from nitrogen and hydrogen. N heat exchanger catalytic converter condenser N 3 What is the purpose of the heat exchanger? to cool the incoming gas mixture to avoid overheating the catalyst to cool the reaction products and separate the N 3 from unused N 2 and 2 to warm the incoming gas mixture and shift the equilibrium to give more N 3 to warm the incoming gas mixture and speed up the reaction 19 Total elimination of the pollutant sulphur dioxide, SO 2, is difficult, both for economic and technical reasons. Its emission can be reduced in furnace chimneys using desulphurisation plants, where the gases are scrubbed (washed) with calcium hydroxide to remove the SO 2. What is the main product formed initially? ao a(o) 2 aso 3 aso 4 2 Which pair of reaction types is illustrated by the reaction sequence below? I in 3 O 2 NaO(aq) 3 = I (O) 3 electrophilic addition and electrophilic substitution electrophilic addition and nucleophilic substitution nucleophilic addition and electrophilic substitution nucleophilic addition and nucleophilic substitution ULES /1/M/J/8

9 21 Trichloroethene is widely used as a dry-cleaning agent. 9 l l l With which of the following does trichloroethene react to give a chiral product? r 2 l NaN(aq) NaO(aq) 22 hloroethene, 2 =l, is the monomer of PV. What are the bond angles along the polymeric chain in PV? They are all alf are 19.5 and half are 12. They are all 12. They are all Which hydrocarbon would not be collected in the inverted tube by heating pentane, 3 ( 2 ) 3 3, in the apparatus shown? pentane on mineral fibre aluminium oxide hydrocarbons very strong heat water = 2 3 ( 2 ) 8 3 ULES /1/M/J/8 [Turn over

10 1 24 valonic acid, 3,5-dihydroxy-3-methylpentanoic acid, is involved in cholesterol formation in the body. It is an oil that occurs as a mixture of the two interchanging molecules shown in the diagram. O 3 I O O 2 II O O O What names are used to describe the pair of interchanging reactions I and II? condensation and addition dehydrogenation and hydrogenation esterification and hydrolysis neutralisation and acidification 25 alogenoalkanes are important molecules in organic synthetic reactions. In particular they undergo a range of nucleophilic reactions. Which reaction proceeds only by an S N 1 mechanism? 3 2 r + N I + O 3 r 3 + N 3 ( 3 ) 3 I + O 26 n alcohol of molecular formula 4 1 O 2 contains two O groups and has an unbranched carbon atom chain. On reaction with an excess of hot molecular formula 4 6 O 4. MnO 4 / + this alcohol is converted into a compound of To which two carbon atoms in the chain of the alcohol are the two O groups attached? 1st and 2nd 1st and 3rd 1st and 4th 2nd and 3rd ULES /1/M/J/8

11 11 27 ompound X has the molecular formula 1 14 O; is unreactive towards mild oxidising agents. What is the structure of the compound formed by dehydration of X? Ethanal, 3 O, can be reduced using an aqueous methanolic solution of Na 4 as the reducing agent. This is a nucleophilic addition reaction. What could be the first step of this mechanism? attack of an + ion at the carbon atom of the carbonyl group attack of an + ion at the oxygen atom of the carbonyl group attack of an ion at the carbon atom of the carbonyl group attack of an ion at the oxygen atom of the carbonyl group 29 Which compound is both chiral and acidic? O 2 3 O 2 r O 2 (O)O 2 2 O 2 3 O 2 ULES /1/M/J/8 [Turn over

12 3 ompound X, 6 12 O, is oxidised by acidified sodium dichromate(vi) to compound Y. 12 ompound Y reacts with ethanol in the presence of a little concentrated sulphuric acid to give liquid Z. What is the formula of Z? 3 ( 2 ) 2 =O 2 3 ( 2 ) 4 2 O ( 2 ) 4 O O 2 ( 2 ) 4 3 ULES /1/M/J/8

13 13 Section or each of the questions in this section, one or more of the three numbered statements 1 to 3 may be. ecide whether each of the statements is or is not (you may find it helpful to put a tick against the statements that you consider to be ). The responses to should be selected on the basis of 1, 2 and 3 are 1 and 2 only are 2 and 3 only are 1 only is No other combination of statements is used as a response. 31 or complete combustion, 1 mol of an organic compound X was found to require 2.5 mol of molecular oxygen. Which compounds could be X? O O 32 atalysts are used in many reversible reactions in the chemical industry. Vanadium(V) oxide is used in this way in the ontact process for the formation of SO 3. 2SO 2 (g) + O 2 (g) 2SO 3 (g) What effect does vanadium(v) oxide have on this equilibrium? 1 It speeds up the forward reaction. 2 It increases the value of K p. 3 It increases the value of E a for the reverse reaction. 33 Which statements about the properties of a catalyst are? 1 catalyst increases the average kinetic energy of the reacting particles. 2 catalyst increases the rate of the reverse reaction. 3 catalyst has no effect on the enthalpy change of the reaction. ULES /1/M/J/8 [Turn over

14 14 The responses to should be selected on the basis of 1, 2 and 3 are 1 and 2 only are 2 and 3 only are 1 only is No other combination of statements is used as a response. 34 Water is added to anhydrous aluminium chloride to make a.1 mol dm -3 solution. Which observations are? 1 The reaction is endothermic. 2 The solution is acidic. 3 The solution contains the ion [l( 2 O) 6 ] The electronic structure of the outer shell of the element radium is 7s 2. Which statements will be for radium within its group? 1 The element will decompose water, liberating hydrogen. 2 The element will show an oxidation number of +2 in all its compounds. 3 Radium has the highest first ionisation energy. 36 When the yellow liquid Nl 3 is stirred into aqueous sodium hydroxide, the reaction that occurs can be represented by the following equation. 2Nl 3 (l) + 6NaO(aq) N 2 (g) + 3Nal (aq) + 3NaOl (aq) O(l) What will be the result of this reaction? 1 The nitrogen is oxidised. 2 bleaching solution remains after the reaction. 3 The final solution gives a precipitate with acidified silver nitrate. ULES /1/M/J/8

15 15 37 spirin is a widely-available pain-killer, whose properties have been known for centuries. The structure of aspirin is shown. O O O Which functional groups are present in aspirin? 1 alcohol 2 carboxylic acid 3 ester O 3 38 The structure of monosodium glutamate, a flavour enhancer, is shown. Na + O 2 2 O 2 O N 2 It may be prepared starting from the following compound. l 2 2 O 2 N 2 Which set of reagents and reaction conditions could be used to prepare monosodium glutamate? 1 eat under reflux with ethanolic KN followed by hydrolysis with NaO(aq). 2 eat with sodium methanoate, O2 Na +. 3 eat under reflux with NaO(aq). ULES /1/M/J/8 [Turn over

16 16 The responses to should be selected on the basis of 1, 2 and 3 are 1 and 2 only are 2 and 3 only are 1 only is No other combination of statements is used as a response. 39 The compound cholesterol has the following structure O 2 Which statements are? 1 holesterol reacts with a mixture of ethanoic acid and concentrated sulphuric acid. 2 holesterol reacts with bromine to form a compound which has two new chiral centres. 3 holesterol is oxidised by acidified sodium dichromate(vi) to form an aldehyde. 4 erulic acid is an antioxidant that occurs widely in plants. O =O 2 3 O ferulic acid Which reagents can react with the =O 2 part of the molecule? 1 NaO(aq) 2 acidified KMnO 4 3 r Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (ULES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of ambridge International Examinations is part of the ambridge ssessment Group. ambridge ssessment is the brand name of University of ambridge Local Examinations Syndicate (ULES), which is itself a department of the University of ambridge. ULES /1/M/J/8

Cambridge International Examinations Cambridge International Advanced Subsidiary and Advanced Level

Cambridge International Examinations Cambridge International Advanced Subsidiary and Advanced Level *2230209778* ambridge International Examinations ambridge International dvanced Subsidiary and dvanced Level EMISTRY 9701/13 Paper 1 Multiple hoice ctober/november 2018 dditional Materials: Multiple hoice