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Surname For Examiner’s Use Other Names Centre Number Candidate Number Candidate Signature General Certificate of Education June 2009 Advanced Subsidiary Examination CHEMISTRY Unit 3(a) Introduction to Organic Chemistry Wednesday 3 June 2009 CHM3/W 9.00 am to 10.00 am For this paper you must have ● the Periodic Table/Data Sheet provided as an insert (enclosed) ● a calculator. For Examiner’s Use Question Mark Question Mark 1 Time allowed: 1 hour 2 Instructions ● Use black ink or black ball-point pen. ● Fill in the boxes at the top of this page. ● Answer all questions. ● Answer the questions in Section A and Section B in the spaces provided. Answers written in margins or on blank pages will not be marked. ● Your answers to Section B should be on the pages indicated. ● All working must be shown. ● Do all rough work in this book. Cross through any work you do not want to be marked. ● The Periodic Table/Data Sheet is provided as an insert. 3 Information ● The maximum mark for this paper is 60. ● The marks for questions are shown in brackets. ● You are expected to use a calculator where appropriate. ● Write your answer to the questions in Section B in continuous prose, where appropriate. ● You will be assessed on your ability to use good English, to organise information clearly and to use specialist vocabulary, where appropriate. 4 5 6 7 8 Total (Column 1) → Total (Column 2) → TOTAL Examiner’s Initials Advice ● You are advised to spend about 45 minutes on Section A and about 15 minutes on Section B. (JUN09CHM3W01) APW/Jun09/CHM3/W CHM3/W 2 Areas outside the box will not be scanned for marking SECTION A Answer all questions in the spaces provided. 1 Crude oil is a mixture which can be separated into fractions. These fractions contain saturated hydrocarbons that belong to the homologous series of alkanes. 1 (a) (i) Name the process by which crude oil can be separated into fractions. ................................................................................................................................... (1 mark) 1 (a) (ii) State what is meant by the term saturated, as applied to a hydrocarbon. ................................................................................................................................... ................................................................................................................................... (1 mark) 1 (b) Each homologous series can be represented by a general formula. State two other characteristics of homologous series. Characteristic 1 ................................................................................................................. ............................................................................................................................................. Characteristic 2 ................................................................................................................. ............................................................................................................................................. (2 marks) 1 (c) Fractions from crude oil can be converted into different substances by catalytic cracking or by thermal cracking. 1 (c) (i) Explain what is meant by the term cracking. ................................................................................................................................... ................................................................................................................................... ................................................................................................................................... (2 marks) (02) APW/Jun09/CHM3/W 3 1 (c) Areas outside the box will not be scanned for marking (ii) Apart from the use of a catalyst, state how one of the conditions for catalytic cracking differs from that used for thermal cracking. ................................................................................................................................... ................................................................................................................................... (1 mark) 1 (c) (iii) State one way in which the products formed by catalytic cracking differ from those formed by thermal cracking. ................................................................................................................................... ................................................................................................................................... (1 mark) 8 Turn over for the next question Turn over (03) APW/Jun09/CHM3/W 4 There are no questions printed on this page DO NOT WRITE ON THIS PAGE ANSWER IN THE SPACES PROVIDED (04) APW/Jun09/CHM3/W 5 Areas outside the box will not be scanned for marking 2 The alkanes are used mainly as fuels. 2 (a) The empirical formula and the molecular formula of undecane are both C11H24 2 (a) (i) State what is meant by the term empirical formula. ................................................................................................................................... ................................................................................................................................... (1 mark) 2 (a) (ii) Give the molecular formula of an alkane with 15 carbon atoms. ................................................................................................................................... (1 mark) 2 (a) (iii) State what is meant by the term fuel. ................................................................................................................................... ................................................................................................................................... (1 mark) 2 (a) (iv) Write an equation for the complete combustion of undecane (C11H24). ................................................................................................................................... (1 mark) 2 (b) Ethanol can also be used as a fuel in the engine of a motor car. Write an equation for the incomplete combustion of ethanol to form carbon monoxide and water only. ............................................................................................................................................. (1 mark) 5 Turn over (05) APW/Jun09/CHM3/W 6 Areas outside the box will not be scanned for marking 3 The mechanism for the reaction of fluorine with difluoromethane (CH2F2) is a free-radical substitution similar to the reaction of chlorine with methane. 3 (a) Write an equation for each of the following steps in the mechanism for the reaction of fluorine with difluoromethane to form trifluoromethane (CHF3). Initiation step ............................................................................................................................................. First propagation step ............................................................................................................................................. Second propagation step ............................................................................................................................................. A termination step in which C2H2F4 is formed ............................................................................................................................................. (4 marks) 3 (b) Heptafluoropropane (C3HF7) is used to extinguish fires that occur in electrical equipment. 3 (b) (i) Balance the following equation. C3H8 + …… F2 3 (b) C3HF7 + …… HF (1 mark) (ii) Draw the structure of one of the possible isomers of C3HF7 (1 mark) (06) APW/Jun09/CHM3/W 7 3 Areas outside the box will not be scanned for marking (c) Halon 1301 was used in fire extinguishers before the introduction of heptafluoropropane. Halon 1301 is a compound which contains 8.1 % carbon and 53.7 % bromine by mass. The remainder of the compound is fluorine. Calculate the empirical formula of Halon 1301. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. (3 marks) 9 Turn over for the next question Turn over (07) APW/Jun09/CHM3/W 8 Areas outside the box will not be scanned for marking 4 The table shows five structural isomers. Structure Isomer 1 Name CH2 H2C CH2 H2C CH2 CH2 Isomer 2 H CH3CH2CH2 C C CH3 hex-2-ene H 2-methylpent-1-ene H Isomer 3 CH3 CH3CH2CH2 C C H Isomer 4 CH3 CH3CH2 C C CH3 3-methylpent-2-ene H Isomer 5 CH3 CH3 C C CH3 CH3 4 (a) Complete the table by naming Isomer 1 and Isomer 5. 4 (b) State what is meant by the term structural isomers. (2 marks) ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. (2 marks) (08) APW/Jun09/CHM3/W 9 4 (c) Areas outside the box will not be scanned for marking (i) State the type of structural isomerism shown by Isomer 1 when it is compared to the other four isomers in the table. ................................................................................................................................... (1 mark) 4 (c) (ii) Identify the isomers from the table that exist as stereoisomers. ................................................................................................................................... ................................................................................................................................... (2 marks) 4 (c) (iii) Draw the structure of a position isomer of hex-2-ene. (1 mark) 4 (d) Name and outline a mechanism for the reaction of bromine with Isomer 5. Name of mechanism ........................................................................................................... Mechanism (5 marks) 13 Turn over (09) APW/Jun09/CHM3/W 10 Areas outside the box will not be scanned for marking 5 Consider the following two reaction sequences. KOH(aq) CH3CHBrCH3 CH3CH(OH)CH3 2-bromopropane K2Cr2O7/H2SO4 O CH3 C P KOH(aq) CH3CH2CH2Br CH3CH2CH2OH 1-bromopropane Q CH3 R K2Cr2O7/H2SO4 O CH3CH2 C H S K2Cr2O7/H2SO4 compound T 5 (a) Name and outline a mechanism for the conversion of 2-bromopropane into compound P. Name of mechanism ........................................................................................................... Mechanism (3 marks) 5 (b) State the class of alcohols to which compound P belongs and give the name of compound R. Class of alcohols ................................................................................................................ Name of R .......................................................................................................................... (2 marks) (10) APW/Jun09/CHM3/W 11 5 Areas outside the box will not be scanned for marking (c) A simple chemical test can be used to distinguish between separate samples of R and S. Suggest a suitable test reagent and state what you would observe in each case. Test reagent ........................................................................................................................ Observation with R ............................................................................................................ Observation with S ............................................................................................................ (3 marks) 5 (d) (i) Draw the structure of T. (1 mark) 5 (d) (ii) State the type of reaction that occurs in the conversion of S into T. ................................................................................................................................... (1 mark) 10 Turn over for the next question Turn over (11) APW/Jun09/CHM3/W 12 Areas outside the box will not be scanned for marking SECTION B Answer each question in the space provided. 6 Consider the following reaction sequence. CH3 CH3 CH3 C C Br Br CH3 CH3 Reaction 1 CH3 CH3 KOH(ethanol) C C CH2 Br Reaction 2 CH3 CH3 CH3 C C H H CH3 CH3 Reaction 3 CH3 H2C C C CH2 Outline a mechanism for the elimination reaction shown in Reaction 1. Give a reagent and catalyst for Reaction 3. ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... (5 marks) 5 (12) APW/Jun09/CHM3/W 13 Areas outside the box will not be scanned for marking 7 Ethanol can be manufactured by two different processes. One process uses ethene and the other uses glucose. Process 1 H2C CH2 + H2O CH3CH2OH ethene Process 2 C6H12O6 2CH3CH2OH + 2CO2 glucose For each process, name the type of reaction and give a suitable catalyst. Give one advantage that each process has over the other. ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... (6 marks) 6 Turn over (13) APW/Jun09/CHM3/W 14 Areas outside the box will not be scanned for marking 8 Write an equation for the reaction in which epoxyethane is manufactured on an industrial scale. Identify the catalyst used and show clearly the structure of epoxyethane. Write an equation for the reaction of one molecule of epoxyethane with one molecule of water. ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... ...................................................................................................................................................... (4 marks) 4 END OF QUESTIONS (14) APW/Jun09/CHM3/W 15 There are no questions printed on this page DO NOT WRITE ON THIS PAGE ANSWER IN THE SPACES PROVIDED (15) APW/Jun09/CHM3/W 16 There are no questions printed on this page DO NOT WRITE ON THIS PAGE ANSWER IN THE SPACES PROVIDED Copyright © 2009 AQA and its licensors. All rights reserved. (16) APW/Jun09/CHM3/W General Certificate of Education June 2009 Advanced Subsidiary Examination CHEMISTRY Unit 3(a) Introduction to Organic Chemistry CHM3/W Gas constant R = 8.31 J K–1 mol–1 Table 1 Proton n.m.r. chemical shift data Type of proton δ/ppm RCH3 0.7–1.2 R2CH2 1.2–1.4 R3CH 1.4–1.6 RCOCH3 2.1–2.6 ROCH3 3.1–3.9 RCOOCH3 3.7–4.1 ROH 0.5–5.0 Table 2 Infra-red absorption data Insert to APW/Jun09/CHM3/W Bond Wavenumber/cm–1 C—H 2850–3300 C—C 750–1100 C C 1620–1680 C O 1680–1750 C—O 1000–1300 O—H (alcohols) 3230–3550 O—H (acids) 2500–3000 Insert to APW/Jun09/CHM3/W H * 89 † 90 – 103 Actinides † Actinium Ac 227 57 Lanthanum La 138.9 39 Yttrium Y 88.9 21 Scandium Sc 45.0 Lanthanides 88 * 58 – 71 87 Ra Radium Fr 223.0 Francium 56 226.0 55 Ba Barium 132.9 Cs 38 137.3 37 Caesium Sr Strontium Rb 85.5 Rubidium 20 87.6 19 Ca Calcium K 40.1 39.1 Potassium 12 11 Mg Magnesium Na 23.0 Sodium 4 24.3 3 Be Beryllium Li 9.0 II 72 Hafnium Hf 178.5 40 Zirconium Zr 91.2 22 Titanium Ti 47.9 24 25 Tc 98.9 26 Ru 101.1 Iron Fe 55.8 43 44 45 Sm 150.4 77 Iridium Ir 192.2 46 Eu 152.0 78 Platinum Pt 195.1 Protactinium Th Thorium 91 Pa 59 231.0 92 Uranium U 238.0 60 93 Neptunium Np 237.0 61 94 Plutonium Pu 239.1 62 95 Americium Am 243.1 63 Pm 144.9 76 Osmium Os 190.2 Palladium Pd 106.4 28 Nickel Ni 58.7 Europium Nd 144.2 75 Rhenium Re 186.2 Rhodium Rh 102.9 27 Cobalt Co 58.9 Praseodymium Neodymium Promethium Samarium Pr 140.9 74 Tungsten W 183.9 42 Molybdenum Technetium Ruthenium Mo 95.9 58 90 Mn 54.9 3 Li Lithium 6.9 Chromium Manganese Cr 52.0 232.0 Cerium Ce 140.1 73 Tantalum Ta 180.9 41 Niobium Nb 92.9 23 Vanadium V 50.9 atomic number relative atomic mass Key 47 96 Curium Cm 247.1 64 Gadolinium Gd 157.3 79 Gold Au 197.0 Silver Ag 107.9 29 Copper Cu 63.5 30 Al Cf 252.1 66 Dysprosium Dy 162.5 81 Thallium Tl 204.4 49 Indium In 114.8 31 Gallium Ga 13 69.7 Aluminium 6 50 Es (252) 67 Holmium Ho 164.9 82 Lead Pb 207.2 Tin Sn 118.7 32 Germanium Ge 14 72.6 Silicon Si 28.1 Carbon C 12.0 IV 97 98 99 Berkelium Californium Einsteinium Bk 247.1 65 Terbium Tb 158.9 80 Mercury Hg 200.6 48 Cadmium Cd 112.4 Zinc Zn 65.4 5 27.0 Boron B 10.8 III 7 100 Fermium Fm (257) 68 Erbium Er 167.3 83 Bismuth Bi 209.0 51 Antimony Sb 121.8 33 Arsenic As 15 74.9 Phosphorus P 31.0 Nitrogen N 14.0 V The atomic numbers and approximate relative atomic masses shown in the table are for use in the examination unless stated otherwise in an individual question. Lithium 1 6.9 Hydrogen 1.0 I ■ The Periodic Table of the Elements 8 101 Mendelevium Md (258) 69 Thulium Tm 168.9 84 Polonium Po 210.0 52 Tellurium Te 127.6 34 Selenium Se 16 79.0 Sulphur S 32.1 Oxygen O 16.0 VI 9 102 Nobelium No (259) 70 Ytterbium Yb 173.0 85 Astatine At 210.0 53 Iodine I 126.9 35 Bromine Br 17 79.9 Chlorine Cl 35.5 Fluorine F 19.0 VII He 10 103 Lawrencium Lr (260) 71 Lutetium Lu 175.0 86 Radon Rn 222.0 54 Xenon Xe 131.3 36 Krypton Kr 18 83.8 Argon Ar 39.9 Neon Ne 2 20.2 Helium 4.0 0