12188 15 Methyl red is a dye and can be used as an indicator. It is synthesised by the reaction of dimethylaniline with the diazonium salt of anthranilic acid. O NH2 HO O N N + HO O N HO N N N methyl red (a) Name the reagents used to produce the diazonium ion and the condition under which they are used. [2] (b) (i) Explain why methyl red is a coloured compound. [4] 12188 [Turn over (ii) Methyl red is red in its acidic form and yellow in its basic form. N H3C CH3 N N COO− H H3C CH3 COO− N N N + +H+ −H+ ⇌ basic form acidic form Suggest why the two forms have different colours. [2] (c) Methyl red is insoluble in water. It forms a sodium salt which has a solubility of 800 mg in 1 cm3 of water. Explain why methyl red is insoluble in water but the sodium salt is soluble in water. [2] 12188 (d) The synthesis of anthranilic acid may be carried out as follows. CH3 CH3 NO2 COOH NO2 COOH NH2 (i) Name the reagents used to carry out the nitration of methylbenzene. [2] (ii) The reagent used to oxidise the 2-methylnitrobenzene is acidified potassium manganate(VII). State the colour change observed. [2] 12188 (e) The reduction of the nitrobenzoic acid is carried out using tin and concentrated hydrochloric acid. (i) Write the equation for the reaction of tin with hydrochloric acid. [2] (ii) The anthranilic acid is obtained as the phenylammonium salt. Draw the structure of the salt and explain why the addition of sodium hydroxide solution liberates the amino group but does not produce anthranilic acid. [3] THIS IS THE END OF THE QUESTION PAPER 12188 BLANK PAGE DO NOT WRITE ON THIS PAGE 12188 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. 243678 DO NOT WRITE ON THIS PAGE Data Leaflet 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 New Specification © CCEA 2017 For first teaching from September 2016 For first award of AS Level in Summer 2017 For first award of A Level in Summer 2018 Subject Code: 1110 General Information 1 tonne = 106 g 1 metre = 109nm One mole of any gas at 293K and a pressure of 1 atmosphere (105Pa) occupies a volume of 24 dm3 Avogadro Constant = 6.02 × 1023 mol–1 Planck Constant = 6.63 × 10–34 Js Specific Heat Capacity of water = 4.2 J g–1K–1 Speed of Light = 3 × 108 ms–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 C6H5–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. 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)