Preface |
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xvii | |
Acknowledgements |
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xviii | |
Contributors |
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xix | |
About the companion website |
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xx | |
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1 | (1) |
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0.1 Introduction to chemistry |
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1 | (1) |
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0.2 Measurement in chemistry and science - SI units |
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2 | (2) |
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0.3 Expressing large and small numbers using scientific notation |
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4 | (2) |
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0.4 Using metric prefixes |
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6 | (4) |
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0.4.1 Units of mass and volume used in chemistry |
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7 | (3) |
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10 | (2) |
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0.6 Calculations using scientific notation |
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12 | (2) |
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0.6.1 Adding and subtracting |
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12 | (1) |
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0.6.2 Multiplying and dividing numbers |
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13 | (1) |
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0.7 Writing chemical formulae and equations |
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14 | (7) |
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0.7.1 Writing chemical formulae |
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14 | (1) |
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0.7.2 Writing and balancing chemical equations |
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15 | (2) |
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0.7.3 Indicating the physical state of reactants and products in chemical equations |
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17 | (1) |
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17 | (1) |
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18 | (3) |
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21 | (18) |
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21 | (4) |
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1.1.1 Subatomic particles |
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21 | (1) |
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1.1.2 Mass number (A) and atomic number (Z) |
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22 | (1) |
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23 | (1) |
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24 | (1) |
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25 | (14) |
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25 | (1) |
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1.2.2 Electron energy levels |
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26 | (1) |
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1.2.3 Simple electronic configurations |
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27 | (2) |
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1.2.4 Sub-shells and atomic orbitals |
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29 | (2) |
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1.2.5 Describing electronic configurations |
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31 | (2) |
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1.2.6 Electronic structures and the periodic table |
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33 | (4) |
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37 | (1) |
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37 | (2) |
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39 | (32) |
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39 | (10) |
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2.1.1 Atoms and molecules |
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39 | (1) |
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40 | (1) |
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41 | (4) |
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45 | (4) |
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2.2 Valence Shell Electron Pair Repulsion Theory (VSEPR) |
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49 | (8) |
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2.2.1 How to determine the number of areas of electron density around a central atom |
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50 | (1) |
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2.2.2 Two electron centres around the central atom: linear molecules |
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50 | (1) |
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2.2.3 Three electron centres around the central atom: trigonal planar molecules |
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51 | (1) |
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2.2.4 Four electron centres around the central atom: tetrahedral, pyramidal, and bent molecules |
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52 | (1) |
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2.2.5 Five electron centres around the central atom: trigonal bipyramidal molecules |
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53 | (1) |
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2.2.6 Six electron centres around the central atom: octahedral molecules |
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54 | (3) |
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2.3 Polar bonds and polar molecules |
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57 | (4) |
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57 | (2) |
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59 | (1) |
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60 | (1) |
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2.4 Intermolecular forces |
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61 | (10) |
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2.4.1 Permanent dipole-permanent dipole interactions |
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63 | (1) |
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2.4.2 London dispersion forces (instantaneous dipole-induced dipole) |
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63 | (1) |
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64 | (1) |
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2.4.4 Summary of strengths of intermolecular forces |
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65 | (2) |
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2.4.5 A special case: ion-dipole intermolecular forces |
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67 | (1) |
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67 | (1) |
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68 | (3) |
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71 | (30) |
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3.1 Masses of atoms and molecules |
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72 | (2) |
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3.1.1 Relative atomic mass, Ar |
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72 | (1) |
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3.1.2 Relative molecular mass, Mr |
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72 | (1) |
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3.1.3 Relative formula mass |
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73 | (1) |
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74 | (2) |
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74 | (1) |
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3.2.2 Converting between moles and masses of substances - molar mass |
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75 | (1) |
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3.3 Calculations with moles |
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76 | (10) |
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77 | (2) |
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79 | (2) |
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3.3.3 Percentage composition by mass |
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81 | (2) |
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83 | (3) |
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3.4 Solutions; concentrations, and dilutions |
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86 | (5) |
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3.4.1 Measuring and expressing concentrations |
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86 | (2) |
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3.4.2 Solutions and dilutions |
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88 | (2) |
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3.4.3 Alternative units of concentration |
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90 | (1) |
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3.5 Titration calculations |
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91 | (5) |
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94 | (2) |
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3.6 Calculations with gas volumes |
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96 | (5) |
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98 | (1) |
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99 | (2) |
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101 | (30) |
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101 | (2) |
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103 | (4) |
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103 | (1) |
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104 | (1) |
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4.2.3 Simple molecular solids and giant molecular structures |
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105 | (2) |
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107 | (13) |
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4.3.1 Evaporation and condensation, vapour pressure, and boiling |
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108 | (1) |
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4.3.2 Effect of intermolecular forces on melting and boiling points |
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109 | (4) |
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4.3.3 The effect of hydrogen bonding on melting and boiling points of covalent compounds |
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113 | (7) |
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120 | (11) |
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120 | (1) |
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4.4.2 The ideal gas equation |
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120 | (5) |
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4.4.3 The molar gas volume, Vm |
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125 | (1) |
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126 | (1) |
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127 | (4) |
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5 Oxidation-reduction (redox) reactions |
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131 | (18) |
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131 | (11) |
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5.1.1 Electron transfer in redox reactions |
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131 | (2) |
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133 | (2) |
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5.1.3 Naming compounds based on the oxidation state of elements in the compound |
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135 | (2) |
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5.1.4 Redox half-equations |
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137 | (3) |
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5.1.5 Oxidising agents and reducing agents |
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140 | (2) |
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5.2 Disproportionate reactions |
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142 | (1) |
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143 | (6) |
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146 | (1) |
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146 | (3) |
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6 Energy, enthalpy, and entropy |
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149 | (54) |
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150 | (36) |
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6.1.1 Energy and enthalpy |
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150 | (1) |
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6.1.2 Exothermic and endothermic reactions |
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151 | (1) |
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6.1.3 Reaction pathway diagrams |
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152 | (1) |
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6.1.4 Measuring enthalpy changes |
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153 | (1) |
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6.1.5 Measuring enthalpy changes using calorimetry |
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154 | (10) |
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164 | (5) |
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6.1.7 Bond energies and enthalpy changes |
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169 | (5) |
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174 | (10) |
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6.1.9 Factors affecting the size of the lattice enthalpy |
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184 | (2) |
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6.2 Entropy and Gibbs free energy |
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186 | (17) |
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187 | (3) |
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6.2.2 Spontaneous processes and the second law of thermodynamics |
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190 | (4) |
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6.2.3 Gibbs free energy and spontaneous reactions |
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194 | (4) |
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198 | (1) |
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199 | (4) |
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7 Chemical equilibrium and acid-base equilibrium |
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203 | (52) |
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204 | (1) |
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7.2 Equilibrium and reversible reactions |
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204 | (20) |
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7.2.1 Characteristics of an equilibrium |
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205 | (1) |
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7.2.2 The equilibrium mixture and the equilibrium constant, Kc |
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205 | (9) |
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7.2.3 The effects of changing the reaction conditions on the position of equilibrium |
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214 | (6) |
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7.2.4 Heterogeneous and homogeneous equilibria |
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220 | (1) |
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7.2.5 The equilibrium constant, Kp |
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221 | (3) |
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224 | (31) |
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7.3.1 The Brensted-Lowry theory of acids and bases |
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224 | (5) |
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229 | (2) |
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7.3.3 Strong and weak acids and bases |
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231 | (3) |
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7.3.4 The ionisation of water |
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234 | (2) |
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7.3.5 Acid-base reactions |
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236 | (1) |
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7.3.6 Carrying out a titration |
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237 | (1) |
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238 | (2) |
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7.3.8 Acid-base titrations |
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240 | (3) |
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243 | (3) |
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7.3.10 Calculating the pH of a buffer solution |
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246 | (3) |
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7.3.11 Lewis acids and bases |
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249 | (1) |
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250 | (1) |
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251 | (4) |
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8 Chemical kinetics -- the rates of chemical reactions |
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255 | (44) |
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256 | (1) |
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256 | (9) |
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8.2.1 Defining the rate of a chemical reaction |
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256 | (3) |
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259 | (1) |
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8.2.3 Factors that affect the rate of a reaction |
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260 | (5) |
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8.3 Determining the rate of a chemical reaction |
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265 | (3) |
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8.3.1 Methods of monitoring the rate of a chemical reaction |
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265 | (1) |
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8.3.2 The instantaneous rate of reaction |
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265 | (2) |
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8.3.3 An example of measuring rate of reaction at any time |
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267 | (1) |
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268 | (11) |
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8.4.1 Determining the rate expression using instantaneous rates |
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270 | (1) |
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8.4.2 Determining the rate expression using the initial rates method |
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270 | (3) |
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8.4.3 Determining the rate expression by inspection |
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273 | (2) |
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8.4.4 Determining the rate expression using the integrated rate expression |
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275 | (4) |
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8.5 The half-life of a reaction |
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279 | (7) |
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8.5.1 Half-life of first-order reactions |
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280 | (1) |
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8.5.2 Half-life of zero-order reactions |
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281 | (1) |
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8.5.3 Half-life of second-order reactions |
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282 | (4) |
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286 | (4) |
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8.6.1 Reaction mechanisms and the rate-determining step |
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286 | (1) |
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8.6.2 Using the rate expression to determine the mechanism of a reaction |
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287 | (3) |
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8.7 Effect of temperature on reaction rate |
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290 | (9) |
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8.7.1 The distribution of the energies of molecules with temperature |
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290 | (1) |
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8.7.2 The Arrhenius equation |
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290 | (3) |
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293 | (1) |
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294 | (5) |
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299 | (30) |
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300 | (1) |
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9.2 Using redox reactions |
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300 | (17) |
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9.2.1 Redox Reactions and electrochemical cells |
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301 | (1) |
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9.2.2 Electrochemical cells and half-cells |
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301 | (5) |
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9.2.3 Standard electrode potentials, Eθ |
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306 | (1) |
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9.2.4 The standard hydrogen electrode |
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306 | (3) |
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9.2.5 Half-cells involving non-metals and non-metal ions |
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309 | (1) |
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310 | (2) |
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9.2.7 Using Ee values to obtain voltages of electrochemical cells |
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312 | (3) |
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9.2.8 Using standard reduction potentials to predict the outcome of redox reactions |
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315 | (1) |
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9.2.9 Relation between Eθ and Gibbs energy |
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316 | (1) |
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9.2.10 The effect of non-standard conditions on cell potential -- the Nernst equation |
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317 | (1) |
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9.3 Using redox reactions -- galvanic cells |
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317 | (4) |
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9.3.1 Galvanic (voltaic) cells |
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317 | (1) |
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9.3.2 The variety of cells |
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318 | (1) |
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9.3.3 Disposable batteries |
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318 | (1) |
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319 | (1) |
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320 | (1) |
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9.4 Using redox reactions - electrolytic cells |
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321 | (8) |
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321 | (1) |
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9.4.2 Electrolysis of molten substances |
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322 | (1) |
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9.4.3 Electrolysis of aqueous solutions |
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323 | (1) |
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9.4.4 Calculating the amount of substance deposited during electrolysis |
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323 | (1) |
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324 | (2) |
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326 | (3) |
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10 Group trends and periodicity |
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329 | (22) |
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10.1 The periodic table: periods, groups, and periodicity |
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329 | (1) |
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10.2 Trends in properties of elements in the same vertical group of the periodic table |
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330 | (7) |
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10.2.1 Electron configuration |
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331 | (1) |
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10.2.2 Effective nuclear charge, Zeff |
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331 | (1) |
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332 | (1) |
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10.2.4 Ionisation energies |
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333 | (1) |
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334 | (1) |
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10.2.6 Electron affinity (electron gain enthalpy) |
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334 | (3) |
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10.3 Trends in properties of elements in the same horizontal period |
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337 | (14) |
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10.3.1 Electron configuration |
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337 | (1) |
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338 | (1) |
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339 | (2) |
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341 | (1) |
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10.3.5 Electron affinity, ΔEAHθ |
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342 | (2) |
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344 | (2) |
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10.3.7 Melting point and boiling point |
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346 | (1) |
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10.3.8 Trends in chemical properties across a period |
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346 | (1) |
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347 | (1) |
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348 | (3) |
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11 The periodic table - chemistry of Groups 1, 2, 7 (17), and transition elements |
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351 | (52) |
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352 | (1) |
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11.2 Group 1 -- the alkali metals |
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352 | (6) |
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11.2.1 Physical properties of Group 1 elements |
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354 | (2) |
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11.2.2 Chemical properties of Group 1 elements |
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356 | (2) |
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11.3 Group 2 -- the alkaline earth metals |
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358 | (12) |
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11.3.1 Physical properties of Group 2 elements |
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359 | (3) |
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11.3.2 Chemical properties of Group 2 elements |
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362 | (1) |
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11.3.3 Some s block compounds and their properties |
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363 | (7) |
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11.4 Group 7 (17) -- the halogens |
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370 | (9) |
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11.4.1 Physical properties of Group 7 (17) elements |
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370 | (3) |
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11.4.2 Reactions of Group 7 (17) elements |
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373 | (6) |
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11.5 The transition elements |
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379 | (24) |
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11.5.1 Physical properties of transition elements |
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380 | (4) |
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11.5.2 Complexes of transition elements |
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384 | (3) |
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387 | (3) |
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11.5.4 Origin of colour in transition metal complexes |
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390 | (2) |
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11.5.5 Isomerism in coordination complexes |
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392 | (1) |
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11.5.6 Ligand substitution in transition metal complexes |
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393 | (2) |
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395 | (2) |
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397 | (6) |
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12 Core concepts and ideas within organic chemistry |
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403 | (28) |
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12.1 Types of molecular formulae |
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403 | (4) |
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12.1.1 Empirical and molecular formulae |
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404 | (1) |
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404 | (2) |
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406 | (1) |
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12.2 Nomenclature of simple alkanes |
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407 | (6) |
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12.2.1 Nomenclature for esters |
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412 | (1) |
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413 | (9) |
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413 | (1) |
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12.3.2 Positional isomerism |
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414 | (1) |
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12.3.3 Functional group isomerism |
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414 | (1) |
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12.3.4 Z and E isomerism (alkenes only) |
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415 | (3) |
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418 | (4) |
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12.3.6 Summary of isomerism |
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422 | (1) |
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12.4 Drawing reaction mechanisms |
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422 | (3) |
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423 | (1) |
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12.4.2 Electrophiles, nucleophiles, and radicals |
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424 | (1) |
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425 | (6) |
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12.5.1 Electrophilic addition (to an alkene) |
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425 | (1) |
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12.5.2 Nucleophilic addition (to a carbonyl group) |
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426 | (1) |
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12.5.3 Electrophilic aromatic substitution |
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426 | (1) |
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12.5.4 Nucleophilic substitution |
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426 | (1) |
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427 | (1) |
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427 | (1) |
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427 | (1) |
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428 | (3) |
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13 Alkanes, alkenes, and alkynes |
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431 | (18) |
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431 | (8) |
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13.1.1 Alkanes and crude oil |
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432 | (1) |
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13.1.2 Combustion of alkanes |
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433 | (1) |
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434 | (2) |
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13.1.4 Reactions of alkanes: radicals |
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436 | (3) |
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439 | (7) |
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13.2.1 Bonding in alkenes |
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439 | (1) |
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440 | (1) |
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440 | (2) |
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13.2.4 Testing for alkenes |
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442 | (1) |
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13.2.5 Reaction of alkenes with electrophiles |
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443 | (2) |
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13.2.6 General reactions of alkenes |
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445 | (1) |
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446 | (3) |
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13.3.1 General reactions of alkynes |
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446 | (1) |
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447 | (1) |
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448 | (1) |
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14 Reactivity of selected homologous series |
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449 | (20) |
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449 | (5) |
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450 | (1) |
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14.1.2 Secondary alcohols |
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450 | (1) |
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451 | (1) |
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14.1.4 Combustion of alcohols |
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451 | (1) |
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14.1.5 Oxidation of alcohols |
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451 | (3) |
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14.2 Aldehydes and ketones |
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454 | (2) |
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14.2.1 Nucleophilic addition |
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454 | (1) |
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14.2.2 Tests for aldehydes and ketones |
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455 | (1) |
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456 | (2) |
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14.3.1 Preparation and properties of carboxylic acids |
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456 | (1) |
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14.3.2 Deprotonation of carboxylic acids |
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457 | (1) |
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14.3.3 Reduction of carboxylic acids |
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458 | (1) |
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458 | (2) |
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14.4.1 Properties of esters |
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458 | (1) |
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14.4.2 Hydrolysis of esters |
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459 | (1) |
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460 | (2) |
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14.5.1 Preparation and properties of amides |
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460 | (1) |
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14.5.2 Hydrolysis of amides |
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461 | (1) |
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462 | (2) |
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462 | (2) |
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464 | (1) |
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14.6.3 Preparation of alkyl amines |
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464 | (1) |
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464 | (5) |
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465 | (1) |
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465 | (1) |
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466 | (3) |
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15 The chemistry of aromatic compounds |
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469 | (18) |
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469 | (8) |
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15.1.1 The structure of benzene |
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469 | (2) |
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471 | (2) |
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15.1.3 The reactivity of benzene |
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473 | (1) |
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15.1.4 Resonance in benzene |
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474 | (2) |
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15.1.5 Substituent effects on reactivity |
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476 | (1) |
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15.2 Reactions of benzene with electrophiles |
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477 | (6) |
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477 | (1) |
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15.2.2 Friedel--Crafts alkylation |
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478 | (1) |
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15.2.3 Friedel--Crafts acylation |
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479 | (1) |
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479 | (1) |
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15.2.5 Substituent effects on position of substitution |
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480 | (1) |
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15.2.6 Reaction of phenol with electrophiles |
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480 | (2) |
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15.2.7 Reaction of toluene with electrophiles |
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482 | (1) |
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15.2.8 Reaction of nitrobenzene with electrophiles |
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482 | (1) |
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483 | (4) |
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484 | (1) |
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485 | (2) |
|
16 Substitution and elimination reactions |
|
|
487 | (12) |
|
16.1 Substitution reactions |
|
|
487 | (5) |
|
|
487 | (2) |
|
|
489 | (3) |
|
16.2 Elimination reactions |
|
|
492 | (3) |
|
|
492 | (1) |
|
|
493 | (2) |
|
16.2.3 Zaitsev and Hofmann alkenes |
|
|
495 | (1) |
|
16.3 Comparison of substitution and elimination reactions |
|
|
495 | (4) |
|
|
495 | (1) |
|
|
496 | (3) |
|
17 Bringing it all together |
|
|
499 | (8) |
|
17.1 Functional group interconversion |
|
|
499 | (1) |
|
17.2 Bringing it all together |
|
|
499 | (8) |
|
|
504 | (1) |
|
|
504 | (3) |
|
|
507 | (8) |
|
|
507 | (8) |
|
18.1.1 Addition polymerisation |
|
|
507 | (2) |
|
|
509 | (1) |
|
18.1.3 Condensation polymerisation |
|
|
509 | (3) |
|
|
512 | (1) |
|
|
512 | (3) |
|
|
515 | (34) |
|
|
515 | (4) |
|
19.1.1 How a mass spectrometer works |
|
|
515 | (1) |
|
19.1.2 Using the data from the mass spectrum |
|
|
516 | (1) |
|
19.1.3 Mass spectrometry in organic chemistry |
|
|
517 | (2) |
|
19.2 Infrared spectroscopy (IR) |
|
|
519 | (4) |
|
19.3 Nuclear magnetic resonance spectroscopy (NMR) |
|
|
523 | (14) |
|
|
523 | (14) |
|
19.3.2 Confirming the identity of O---H and N---H peaks |
|
|
537 | (1) |
|
19.4 Bringing it all together |
|
|
537 | (12) |
|
|
541 | (1) |
|
|
541 | (8) |
Appendix |
|
549 | (2) |
Short end-of-chapter answers |
|
551 | (14) |
Index |
|
565 | |