13619.06R 15 Propene (C3H6) is a raw material obtained from crude oil which can be used to produce many important chemicals. A reaction scheme is shown below. C3H6 C3H8 propene C3H7Br C3H7CI C3H8O C3H6O reaction A reaction D reaction B reaction C (a) State the name of the mechanism for reaction A and reaction B. A B [4] (b) (i) Write an equation for reaction A. [1] (ii) Two isomers of C3H7Br are produced in reaction A. State the IUPAC name of the isomer which is the major product. [1] (iii) Draw a mechanism to show the formation of the major product in reaction A. [3] 13619.06R [Turn over (c) (i) Write the formula of the reagent required in reaction B. [1] (ii) Describe the conditions required for reaction B. [2] (iii) The reagent required in reaction B can also be used, under different conditions, to convert C3H7Br back to C3H6. State the type of reaction which occurs when C3H7Br is converted to C3H6. [1] (d) (i) Draw the structural formulae of the two isomers of C3H6O which are produced in reaction C. [2] (ii) Name the reagent used to carry out reaction C. [1] 13619.06R (e) C3H8 reacts with Cl2 to form C3H7Cl in reaction D. One by-product in this reaction is C6H14. (i) Name the mechanism for this reaction. [1] (ii) Write an equation for the initiation step in this mechanism. [1] (iii) Write equations for the two propagation steps in this mechanism. [2] (iv) Write an equation for a termination step which produces C3H7Cl. [1] (v) Write an equation to show how C6H14 may be produced in this reaction. [1] 13619.06R (f) Pentane, C5H12, is also obtained from crude oil. It has the same relative formula mass as butanal, C4H8O, and a similar relative formula mass to butan-1-ol, C4H9OH. However, the three compounds have very different boiling points. Identify which compound (pentane, butanal or butan-1-ol) has the highest boiling point and which has the lowest boiling point. Explain the variation in boiling points of the three compounds with reference to intermolecular forces. In this question you will be assessed on your written communication skills including the use of specialist scientific terms. [6] THIS IS THE END OF THE QUESTION PAPER 13619.06R BLANK PAGE DO NOT WRITE ON THIS PAGE 13619.06R BLANK PAGE DO NOT WRITE ON THIS PAGE Permission to reproduce all copyright material has been applied for. In some cases, efforts to contact copyright holders may have been unsuccessful and CCEA will be happy to rectify any omissions of acknowledgement in future if notified. DO NOT WRITE ON THIS PAGE SCH24/8 276814 Sources Q7.....© Science Ready Data Leafl et Including the Periodic Table of the Elements For the use of candidates taking Advanced Subsidiary and Advanced Level Examinations Copies must be free from notes or additions of any kind. No other type of data booklet or information sheet is authorised for use in the examinations gce a/as examinations chemistry © CCEA 2017 General Information 1 tonne = 106 g 1 metre = 109 nm One mole of any gas at 293 K and a pressure of 1 atmosphere (105 Pa) occupies a volume of 24 dm3 Avogadro Constant = 6.02 × 1023 mol–1 Planck Constant = 6.63 × 10–34 J s Specifi c Heat Capacity of water = 4.2 J g–1 K–1 Speed of Light = 3 × 108 m s–1 Characteristic absorptions in IR spectroscopy Wavenumber/cm–1 Bond Compound 550–850 C–X (X = Cl, Br, I) Haloalkanes s p u o r g ly kla ,s e n a kl A C – C 0 0 1 1 – 0 5 7 s dic a cily x o b r a c ,sr e ts e ,slo h o cl A O – C 0 0 3 1 – 0 0 0 1 1450–1650 C ̿ s e n e r A C 1600–1700 C ̿ s e n e kl A C 1650–1800 C ̿ ,s e d y h e dla ,sr e ts e ,s dic a cily x o b r a C O s e dir olh c ly c a ,s e di m a ,s e n o t e k 2200–2300 C s elirti N N s dic a cily x o b r a C H – O 0 0 2 3 – 0 0 5 2 s e d y h e dl A H – C 0 5 8 2 – 0 5 7 2 s e n e r a ,s e n e kla ,s p u o r g ly kla ,s e n a kl A H – C 0 0 0 3 – 0 5 8 2 slo h o cl A H – O 0 0 6 3 – 0 0 2 3 s e di m a ,s e ni m A H – N 0 0 5 3 – 0 0 3 3 Proton Chemical Shifts in Nuclear Magnetic Resonance Spectroscopy (relative to TMS) Structure 0.5–2.0 –CH s e n a kla d e t a r u t a S 0.5–5.5 –OH slo h o cl A 1.0–3.0 –NH s e ni m A 2.0–3.0 –CO–CH Ketones C – N – H Amines C 6H5–CH c on ring) 2.0–4.0 X–CH X = Cl or Br (3.0–4.0) ) 0.3 – 0.2 ( I = X 4.5–6.0 –C ̿ CH Alkenes 5.5–8.5 RCONH Amides 6.0–8.0 –C6H5 Arenes (on ring) 9.0–10.0 –CHO Aldehydes 10.0–12.0 –COOH Carboxylic acids on and temperature dependent and may be outside the ranges indicated above. 11331.03 227 89 139 57 256 101 223 87 226 88 261 104 262 105 266 106 264 107 277 108 268 109 271 110 272 111 140 58 141 59 144 60 145 61 150 62 152 63 157 64 159 65 162 66 165 67 167 68 169 69 173 70 175 71 232 90 231 91 238 92 237 93 242 94 243 95 247 96 245 97 251 98 254 99 253 100 254 102 257 103 133 55 137 56 178 72 181 73 184 74 186 75 190 76 192 77 195 78 197 79 201 80 89 39 91 40 103 45 85 37 88 38 93 41 96 42 98 43 101 44 106 46 108 47 112 48 131 54 222 86 210 85 210 84 209 83 207 82 204 81 84 36 79 34 73 32 40 20 39 19 45 21 48 22 51 23 52 24 55 25 56 26 59 27 59 28 64 29 65 30 11 5 12 6 14 7 16 8 19 9 20 10 4 2 40 18 35.5 17 32 16 31 15 28 14 27 13 70 31 75 33 80 35 115 49 119 50 122 51 128 52 127 53 23 11 24 12 7 3 9 4 THE PERIODIC TABLE OF ELEMENTS Group * † 1 1 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 II I III IV VI VII 0 V 285 112 Copernicium * 58 – 71 Lanthanum series † 90 – 103 Actinium series a = relative atomic mass x = atomic symbol b = atomic number a bx (approx) 11331.03