UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS Cambridge International Level 3 Pre-U Certificate Principal Subject

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1 UNIVERSITY OF MRIGE INTERNTIONL EXMINTIONS ambridge International Level 3 Pre-U ertificate Principal Subject HEMISTRY 9791/01 Paper 1 Part Multiple hoice May/June hour * * dditional Materials: RE THESE INSTRUTIONS FIRST Multiple hoice nswer Sheet Soft clean eraser Soft pencil (type or H is recommended) ata ooklet Write in soft pencil. o not use staples, paper clips, highlighters, glue or correction 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. For each question there are four possible answers,, and. hoose the one you consider correct and record your choice in soft pencil on the separate nswer Sheet. Read the instructions on the nswer Sheet very carefully. Each correct answer will score one mark. mark will not be deducted for a wrong answer. ny working should be done in this booklet. This document consists of 14 printed pages and 2 blank pages. I12 06_9791_01/5RP ULES 2012 [Turn over

2 2 1 Which element in period 3 is not correctly described? element bonding structure chlorine covalent simple magnesium metallic giant phosphorus covalent simple silicon covalent simple 2 n exciting chemical demonstration is the barking dog. n equation which describes the reaction is shown. 6NO + 2S 2 3N 2 + 2O + 2SO S 8 arbon disulfide, S 2, is a liquid with a density of 1.26 g cm 3. Which mass of sulfur would be formed from 5.00 cm 3 of S 2 if the reaction proceeded with 100 % yield? g 1.67 g 2.65 g 5.31 g 3 n ion of manganese has an electronic configuration of [r]3d 4. Which compound contains this ion? Mnl 2 MnO Mn 2 O 3 MnO 2 4 n ionic compound Q has an empirical formula NH 2 O, reacts with NaOH(aq) to produce ammonia gas. How many electrons are present in the anion of Q? ULES /01/M/J/12

3 3 5 Oxygen reacts with platinum(vi) fluoride, PtF 6, as shown. O 2 + PtF 6 O 2 + PtF 6 When the first noble gas compound was produced in 1962, it was suggested that xenon should react similarly. Xe + PtF 6 Xe + PtF 6 What is the most likely reason for this suggestion being made? O and Xe have similar electron affinities. O and Xe have similar ionic radii. O 2 and Xe have similar electron configurations. O 2 and Xe have similar first ionisation energies. 6 Which statement about antibonding is not correct? Filling an antibonding orbital lowers the bond order of a molecule by 1. For a given orbital overlap, the antibonding orbital is always higher in energy than the bonding orbital. Stable molecules cannot have any electrons in antibonding orbitals. The antibonding orbitals are found outside the region of space between the two bonding nuclei. 7 The shape of the Pl 5 molecule in the gas phase is trigonal bipyramidal. The chlorine atoms can be replaced one at a time by fluorine atoms, the axial chlorine atoms being replaced first, then the equatorial atoms. Which molecule does not have a dipole moment? Pl F 4 Pl 2F 3 Pl 3F 2 Pl 4F ULES /01/M/J/12 [Turn over

4 8 The diagram shows the energy profile for a simple reaction. 4 energy / kj mol reaction coordinate Which statement about the reaction is correct? The reaction is endothermic and the enthalpy change of reaction ( r H) is +292 kj mol 1. The reaction is endothermic and the enthalpy change of reaction ( r H) is +504 kj mol 1. The reaction is exothermic and the enthalpy change of reaction ( r H) is 292 kj mol 1. The reaction is exothermic and the enthalpy change of reaction ( r H) is 504 kj mol 1. 9 t room temperature, hydrogen peroxide decomposes slowly according to the equation. 2H 2 O 2 (aq) O 2 (g) + 2H 2 O(l) Which statement correctly explains the result of carrying out this decomposition in the presence of a catalyst such as MnO 2? The reaction rate increases because the collision frequency increases due to a decrease in the activation energy. The reaction rate increases because the collision frequency increases due to an increase in the average energy of the molecules. The reaction rate increases because the proportion of successful collisions increases due to a decrease in the activation energy. The reaction rate increases because the proportion of successful collisions increases due to an increase in the average energy of the molecules. ULES /01/M/J/12

5 5 10 n energy change accompanies the reaction shown. K(s) K + (g) + e What is equal to the value of this energy change? the enthalpy change of vaporisation of potassium the first ionisation energy of potassium the sum of the enthalpy change of atomisation and the electron affinity of potassium the sum of the enthalpy change of atomisation and the first ionisation energy of potassium 11 Hot concentrated nitric acid, HNO 3, is a powerful oxidising agent. In its reaction with carbon, the oxidation number of carbon increases by 4 and the oxidation number of nitrogen decreases by 1. How many moles of nitric acid are needed to oxidise one mole of carbon in this reaction? Which compound is not a product of the reaction between an oxide of a period 3 element and water? Mg(OH) 2 H 2 SiO 3 H 3 PO 4 H 2 SO 3 13 When anhydrous sodium carbonate, a white solid, is heated in a roaring unsen flame, it turns into a colourless liquid. Which statement explains this change? It has absorbed water from the atmosphere. It has melted to form liquid sodium carbonate. It has reacted with the air, with water as one of the products. It has thermally decomposed to sodium oxide. ULES /01/M/J/12 [Turn over

6 6 14 The famous volcano chemical demonstration involves ammonium dichromate and can be summarised by the equation. In this reaction, the ammonium ion acts as (NH 4 ) 2 r 2 O 7 N 2 + r 2 O 3 + 4H 2 O an acid. a base. an oxidising agent. a reducing agent. 15 Which quantity is greater for fluorine than for chlorine? bond energy bond length melting point oxidising power 16 Iodine pentoxide, I 2 O 5, is a colourless crystalline solid. arbon monoxide, O, is a reducing agent. When an excess of O is reacted with I 2 O 5, there is no change in gaseous volume after cooling to the original temperature. grey-black solid is produced. When this solid is heated separately, it produces a purple vapour. In which molar ratio do O and I 2 O 5 react? 1 : 1 2 : 5 5 : 1 5 : 2 17 When sucrose, 12 H 22 O 11, is mixed with concentrated sulfuric acid under suitable conditions, a violent reaction occurs producing a black solid and one other product. How does the sulfuric acid behave in this reaction? as a dehydrating agent as a dehydrating agent and an oxidising agent as a strong involatile acid as an oxidising agent ULES /01/M/J/12

7 7 18 Halogenoalkanes and alcohols can be synthesised from each other using the appropriate reagents, as shown. 1-chlorobutane reagent S reagent T butan-1-ol What is the correct combination of reagents for the conversions? reagent S reagent T NaOH(aq) NH 4 l (aq) NaOH(aq) Pl 5 NaOH / ethanol NH 4 l (aq) NH 3 / ethanol Pl 5 19 Which statements about the reaction of butan-2-ol heated under reflux with acidified potassium dichromate(vi) are correct? 1 The organic product contains a π-bond in its molecule. 2 The organic product contains a chiral carbon atom in its molecule. 3 One carbon atom in butan-2-ol increases its functional group level by one. 1, 2 and 3 1 and 2 only 1 and 3 only 2 and 3 only ULES /01/M/J/12 [Turn over

8 8 20 The molecule 24-isopropylcholestane, which has been isolated from a class of sponge, can serve as a biomarker and has determined the first evolutionary appearances of some species. arbon atoms in a molecule are classified as primary, secondary, tertiary or quaternary, depending on whether they are directly bonded to one, two, three or four other carbon atoms. How many tertiary carbons and how many chiral carbons are there in this molecule? tertiary carbons chiral carbons compound of formula 5 H 6 l 2O has the following features. geometric isomers no optical isomers two carbon atoms at the carbonyl functional group level What is the compound? Hl 2OH HH 3 H 2 l OH HH 2 l H 3 Hl l HHO H 3 H 2 OH l 2 22 straight chain organic compound X, 4 H 8 r 2, undergoes hydrolysis with aqueous sodium hydroxide to produce a compound which reacts with Tollens reagent to form a silver mirror. In X, the bromine atoms are joined to carbon atoms numbered 1,1. 1,2. 1,4. 2,2. ULES /01/M/J/12

9 23 affeine is the stimulant found in tea and coffee. The structure of caffeine is shown. 9 H 3 O N O N H 3 N N H How many of its eight carbon atoms are at each of the functional group levels shown? H 3 alcohol carbonyl carboxylic acid carbon dioxide non-cyclic compound has the molecular formula 4 H 9 O 2 N. Which pair of functional groups could not both be present in this molecule? amide and alcohol amine and carboxylic acid amine and ester carboxylic acid and nitrile 25 Which isomer of bromobutanol, 4 H 9 Or, reacts with aqueous sodium hydroxide to give an organic product that has only two peaks in its 13 NMR spectrum? 1-bromobutan-1-ol 3-bromobutan-1-ol 2-bromobutan-2-ol 3-bromobutan-2-ol ULES /01/M/J/12 [Turn over

10 10 26 X is HOH 2 H(OH)HO Y is HOH 2 OH 2 OH Which statement about X and Y is correct? X can be directly oxidised to Y. X and Y have different empirical formulae. X and Y both react with Tollens reagent. X and Y can both be reduced to HOH 2 H(OH)H 2 OH. 27 Grignard reagents react with compounds containing the carbonyl functional group. Which compound would react with Grignard reagent H 3 H 2 Mgr to produce an organic product with a chiral carbon atom? ethanal methanal propanal propanone 28 Elimination occurs when 2,4-dibromoheptane reacts with hot alcoholic sodium hydroxide, producing a mixture of dienes with the molecular formula 7 H 12. Which diene would not be produced in this reaction? H 2 HH 2 H HH 2 H 3 H 2 HH HH 2 H 2 H 3 H 3 H HH 2 H HH 3 H 3 H HH HH 2 H 3 29 In the Krebs cycle, fumaric acid is converted to oxaloacetic acid by a two step process involving an intermediate compound X. What is the identity of X? step 1 step 2 HO 2 H HO 2 H X HO 2 OH 2 O 2 H fumaric acid oxaloacetic acid HO 2 H 2 H 2 O 2 H HO 2 HrH 2 O 2 H HO 2 H(OH)H 2 O 2 H HO 2 H(OH)H(OH)O 2 H ULES /01/M/J/12

11 11 30 Patches used to administer drugs contain pressure-sensitive adhesives that stick to the skin. The diagram shows part of the structure of one such adhesive. H 3 H 3 H 3 H 2 H 2 H 2 H 3 H 3 H 3 Which monomer could be used to make this polymer? H 3 H HH 3 (H 3 ) 2 H(H 3 ) 3 (H 3 ) 2 H 2 (H 3 ) 2 H(H 3 ) 2 H 2 H 3 31 Which type of reaction must have the greatest atom economy? addition condensation elimination substitution 32 gravimetric analysis of a sample of an iron ore was carried out g of ore was dissolved in perchloric acid to oxidise the iron to Fe 3+. The resultant solution was filtered to remove solid impurities and made basic to precipitate the Fe 3+ as a hydrated hydroxide. The precipitate was filtered and heated to produce g of Fe 2 O 3. Which percentage of iron did the ore contain? % % % % 33 large excess of aqueous silver nitrate is added to aqueous barium chloride and the precipitate removed by filtration. What are the most abundant ions in the filtrate? g +, a 2+ and NO 3 g + and NO 3 only a 2+, NO 3 and l a 2+ and NO 3 only ULES /01/M/J/12 [Turn over

12 34 chemist has samples of solutions of aluminium nitrate and lead(ii) nitrate. 12 Which reagent will not be able to distinguish clearly between these two substances? (ll reagents are soluble in water.) Hl KI NaOH Na 2 SO 4 35 In a time-of-flight mass spectrometer, in which order do the fragments arrive at the detector? 1st 2nd 3rd + O 2 H 3 O + + H 3 H 2 NH 3 H 3 O + + O 2 + H 3 H 2 NH 3 + H 3 H 2 NH 3 H 3 O + + O 2 H 3 H 2 NH 3 + O 2 + H 3 O + 36 Which molecule gives large peaks in its mass spectrum at m / z = 29 and m / z = 43? H 2 HH(H 3 ) 2 H 3 H 2 H(H 3 ) 2 H 3 H 2 OOH 2 H 3 H 3 OOH 3 37 Which statement about electronic spectroscopy is not correct? Higher electron shells in hydrogen become closer together in energy. In the atomic emission line spectrum for hydrogen, the convergence limit represents the electron breaking free from the hydrogen atom. The energy of a transition is inversely proportional to the frequency of the photon that is absorbed or emitted. In the hydrogen atom, the subshells within each quantum shell all have the same energy. ULES /01/M/J/12

13 13 38 compound has the molecular formula 5 H 10 O. The diagram shows the infra-red spectrum of the compound. 100 percentage transmittance What is the structural formula of the compound? wavenumber / cm 1 (H 3 ) 2 HOHH 2 H 3 H 2 H 2 H 2 HO H 3 H 2 H 2 OH 3 H 3 (H 3 )HH 2 OH 39 Hexamine is a crystalline white solid that is used as an antibiotic and as solid fuel by campers. N N N N The four nitrogen atoms lie at the corners of a tetrahedron. How many signals are there in the 13 NMR spectrum of hexamine? ULES /01/M/J/12 [Turn over

14 14 40 The 13 NMR spectrum of a compound with formula 4 H 8 O 2 shows peaks at 15 ppm, 20 ppm, 60 ppm and 175 ppm. What is the structure of the compound? HOH 2 HHH 2 OH HOOH(H 3 ) 2 H 3 OOH 2 H 3 H H HO OH H H H H ULES /01/M/J/12

15 15 LNK PGE ULES /01/M/J/12

16 16 LNK PGE 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 /01/M/J/12

Cambridge International Examinations Cambridge International Advanced Subsidiary and Advanced Level

Cambridge International Examinations Cambridge International Advanced Subsidiary and Advanced Level *7608339960* ambridge International Examinations ambridge International dvanced Subsidiary and dvanced Level HEMISTRY 9701/13 Paper 1 Multiple hoice May/June 2017 dditional Materials: Multiple hoice nswer