1. Practical Skills Assessed in a Written Examination1.1 Planning0/01.1.1 Experimental Aims and Design Fundamentals1.1.2 Selecting Apparatus and Techniques1.1.3 Identifying Variables and Controls1.1.4 Evaluating Methods Against Outcomes1.1.5 Applying Prior Chemical Knowledge1.2 Implementing0/01.2.1 Using Practical Apparatus and Techniques Correctly1.2.2 Choosing and Using Appropriate Units1.2.3 Recording Observations and Data1.3 Analysis0/01.3.1 Processing Qualitative and Quantitative Results1.3.2 Mathematical Skills in Data Analysis1.3.3 Significant Figures and Numerical Uncertainty1.3.4 Graph Plotting: Axes, Scales, Quantities and Units1.3.5 Gradients and Intercepts from Graphs1.3.6 Interpreting Trends and Drawing Conclusions1.4 Evaluation0/01.4.1 Evaluating Results and Conclusions1.4.2 Identifying Anomalies1.4.3 Recognising Procedural Limitations1.4.4 Precision, Accuracy and Measurement Error1.4.5 Improving Experimental Design1.4.6 Reliability, Repeatability and Reproducibility1. Practical Skills Assessed in a Written Examination1.1 Planning0/01.1.1 Experimental Aims and Design Fundamentals1.1.2 Selecting Apparatus and Techniques1.1.3 Identifying Variables and Controls1.1.4 Evaluating Methods Against Outcomes1.1.5 Applying Prior Chemical Knowledge1.2 Implementing0/01.2.1 Using Practical Apparatus and Techniques Correctly1.2.2 Choosing and Using Appropriate Units1.2.3 Recording Observations and Data1.3 Analysis0/01.3.1 Processing Qualitative and Quantitative Results1.3.2 Mathematical Skills in Data Analysis1.3.3 Significant Figures and Numerical Uncertainty1.3.4 Graph Plotting: Axes, Scales, Quantities and Units1.3.5 Gradients and Intercepts from Graphs1.3.6 Interpreting Trends and Drawing Conclusions1.4 Evaluation0/01.4.1 Evaluating Results and Conclusions1.4.2 Identifying Anomalies1.4.3 Recognising Procedural Limitations1.4.4 Precision, Accuracy and Measurement Error1.4.5 Improving Experimental Design1.4.6 Reliability, Repeatability and Reproducibility2. Practical Skills Assessed in the Practical Endorsement2.1 Practical skills0/02.1.1 Investigative Approaches and Independent Thinking2.1.2 Safe and Correct Use of Equipment and Materials2.1.3 Following Instructions and Recording Data2.1.4 Presenting Data and Using Digital Tools2.1.5 Research Skills and Referencing2.1.6 Using a Wide Range of Instruments and Techniques2.2 Use of Apparatus and Techniques0/02.2.1 Core Measurements and Heating Methods2.2.2 Measuring and Controlling pH2.2.3 Volumetric Analysis and Solution Preparation2.2.4 Separation, Purification and Reaction Setups2.2.5 Analytical Identification Techniques2.2.6 Electrochemical Cells, Safe Handling and Rates2. Practical Skills Assessed in the Practical Endorsement2.1 Practical skills0/02.1.1 Investigative Approaches and Independent Thinking2.1.2 Safe and Correct Use of Equipment and Materials2.1.3 Following Instructions and Recording Data2.1.4 Presenting Data and Using Digital Tools2.1.5 Research Skills and Referencing2.1.6 Using a Wide Range of Instruments and Techniques2.2 Use of Apparatus and Techniques0/02.2.1 Core Measurements and Heating Methods2.2.2 Measuring and Controlling pH2.2.3 Volumetric Analysis and Solution Preparation2.2.4 Separation, Purification and Reaction Setups2.2.5 Analytical Identification Techniques2.2.6 Electrochemical Cells, Safe Handling and Rates3. Atoms and Reactions3.1 Atomic Structure and Isotopes0/03.1.1 Isotopes and Atomic Structure Basics3.1.2 Atoms and Ions: Protons, Neutrons, Electrons3.1.3 Relative Isotopic Mass and Relative Atomic Mass3.1.4 Mass Spectrometry and Calculating Ar3.1.5 Mr and Relative Formula Mass3.2 Compounds, Formulae and Equations0/03.2.1 Predicting Ionic Charges from the Periodic Table3.2.2 Common Polyatomic Ions to Remember3.2.3 Writing Formulae of Ionic Compounds3.2.4 Balancing Equations with State Symbols3.2.5 Ionic Equations and Spectator Ions3.3 Amount of Substance0/03.3.1 The Mole, Avogadro Constant and Key Terms3.3.2 Empirical and Molecular Formulae3.3.3 Hydrated Salts and Water of Crystallisation3.3.4 Using Moles in Mass, Gases and Solutions3.3.5 Ideal Gas Equation in SI Units3.3.6 Stoichiometry, Yield, Atom Economy and Techniques3.4 Acids0/03.4.1 Common Acids, Alkalis and Ion Definitions3.4.2 Strong and Weak Acids3.4.3 Neutralisation and Salt Formation3.4.4 Preparing a Standard Solution and Titration Technique3.4.5 Titration Calculations3.5 Redox0/03.5.1 Assigning Oxidation Numbers3.5.2 Using Oxidation Numbers in Names and Formulae3.5.3 Redox in Terms of Electrons and Oxidation Numbers3.5.4 Metals with Acids: Equations and Products3.5.5 Interpreting and Predicting Redox Reactions3. Atoms and Reactions3.1 Atomic Structure and Isotopes0/03.1.1 Isotopes and Atomic Structure Basics3.1.2 Atoms and Ions: Protons, Neutrons, Electrons3.1.3 Relative Isotopic Mass and Relative Atomic Mass3.1.4 Mass Spectrometry and Calculating Ar3.1.5 Mr and Relative Formula Mass3.2 Compounds, Formulae and Equations0/03.2.1 Predicting Ionic Charges from the Periodic Table3.2.2 Common Polyatomic Ions to Remember3.2.3 Writing Formulae of Ionic Compounds3.2.4 Balancing Equations with State Symbols3.2.5 Ionic Equations and Spectator Ions3.3 Amount of Substance0/03.3.1 The Mole, Avogadro Constant and Key Terms3.3.2 Empirical and Molecular Formulae3.3.3 Hydrated Salts and Water of Crystallisation3.3.4 Using Moles in Mass, Gases and Solutions3.3.5 Ideal Gas Equation in SI Units3.3.6 Stoichiometry, Yield, Atom Economy and Techniques3.4 Acids0/03.4.1 Common Acids, Alkalis and Ion Definitions3.4.2 Strong and Weak Acids3.4.3 Neutralisation and Salt Formation3.4.4 Preparing a Standard Solution and Titration Technique3.4.5 Titration Calculations3.5 Redox0/03.5.1 Assigning Oxidation Numbers3.5.2 Using Oxidation Numbers in Names and Formulae3.5.3 Redox in Terms of Electrons and Oxidation Numbers3.5.4 Metals with Acids: Equations and Products3.5.5 Interpreting and Predicting Redox Reactions4. Electrons, Bonding and Structure4.1 Electron Structure0/04.1.1 Electron Shells and Capacities4.1.2 Atomic Orbitals and Their Shapes4.1.3 Sub-Shells and Electron Counts4.1.4 Filling Order and Hund’s Rule4.1.5 Electron Configurations of Atoms (Z ≤ 36)4.1.6 Electron Configurations of Ions (S- and P-block)4.2 Bonding and Structure0/04.2.1 Ionic Bonding, Lattices and Properties4.2.2 Covalent Bonding and Bond Strength4.2.3 Molecular Shapes and Bond Angles (VSEPR)4.2.4 Electronegativity, Polar Bonds and Dipoles4.2.5 Intermolecular Forces: Permanent and Induced Dipoles4.2.6 Hydrogen Bonding, Water Anomalies and Simple Lattices4. Electrons, Bonding and Structure4.1 Electron Structure0/04.1.1 Electron Shells and Capacities4.1.2 Atomic Orbitals and Their Shapes4.1.3 Sub-Shells and Electron Counts4.1.4 Filling Order and Hund’s Rule4.1.5 Electron Configurations of Atoms (Z ≤ 36)4.1.6 Electron Configurations of Ions (S- and P-block)4.2 Bonding and Structure0/04.2.1 Ionic Bonding, Lattices and Properties4.2.2 Covalent Bonding and Bond Strength4.2.3 Molecular Shapes and Bond Angles (VSEPR)4.2.4 Electronegativity, Polar Bonds and Dipoles4.2.5 Intermolecular Forces: Permanent and Induced Dipoles4.2.6 Hydrogen Bonding, Water Anomalies and Simple Lattices5. The Periodic Table5.1 Periodicity0/05.1.1 Structure of the Periodic Table5.1.2 Electron Configuration and Block Classification5.1.3 First Ionisation Energy: Definition and Trends5.1.4 Successive Ionisation Energies and Deducing Groups5.1.5 Metallic Bonding and Giant Metallic Lattices5.1.6 Giant Covalent Lattices and Melting Point Variations5.2 Group 20/05.2.1 s2 Configurations and Formation of 2+ Ions5.2.2 Reactions with Oxygen5.2.3 Reactions with Water and Dilute Acids5.2.4 Explaining Reactivity Trends Using Ionisation Energies5.2.5 Hydroxides, Alkalinity Trend and Uses as Bases5.3 The Halogens0/05.3.1 Physical Properties and Boiling-Point Trends5.3.2 Electron Configuration and Redox Behaviour5.3.3 Displacement Reactions and Reactivity Order5.3.4 Explaining Halogen Reactivity Trends5.3.5 Chlorine Disproportionation and Uses5.3.6 Water Treatment: Benefits, Risks and Testing Halides5.4 Qualitative Analysis0/05.4.1 Test Sequence and Rationale5.4.2 Test for Carbonate Ions5.4.3 Test for Sulfate Ions5.4.4 Tests for Halide Ions5.4.5 Test for Ammonium Ions5. The Periodic Table5.1 Periodicity0/05.1.1 Structure of the Periodic Table5.1.2 Electron Configuration and Block Classification5.1.3 First Ionisation Energy: Definition and Trends5.1.4 Successive Ionisation Energies and Deducing Groups5.1.5 Metallic Bonding and Giant Metallic Lattices5.1.6 Giant Covalent Lattices and Melting Point Variations5.2 Group 20/05.2.1 s2 Configurations and Formation of 2+ Ions5.2.2 Reactions with Oxygen5.2.3 Reactions with Water and Dilute Acids5.2.4 Explaining Reactivity Trends Using Ionisation Energies5.2.5 Hydroxides, Alkalinity Trend and Uses as Bases5.3 The Halogens0/05.3.1 Physical Properties and Boiling-Point Trends5.3.2 Electron Configuration and Redox Behaviour5.3.3 Displacement Reactions and Reactivity Order5.3.4 Explaining Halogen Reactivity Trends5.3.5 Chlorine Disproportionation and Uses5.3.6 Water Treatment: Benefits, Risks and Testing Halides5.4 Qualitative Analysis0/05.4.1 Test Sequence and Rationale5.4.2 Test for Carbonate Ions5.4.3 Test for Sulfate Ions5.4.4 Tests for Halide Ions5.4.5 Test for Ammonium Ions6. Physical Chemistry6.1 Enthalpy Changes0/06.1.1 Exothermic and Endothermic Changes; Profiles6.1.2 Activation Energy and Energy Profiles6.1.3 Standard Conditions, States and Key Definitions6.1.4 Determining Enthalpy Changes Experimentally6.1.5 Average Bond Enthalpies and Calculations6.1.6 Hess’ Law and Enthalpy Cycles6.2 Reaction Rates0/06.2.1 Collision Theory and Concentration/Pressure Effects6.2.2 Catalysts and Alternative Pathways6.2.3 Catalysis and Sustainability Considerations6.2.4 Measuring Rates: Techniques and Procedures6.2.5 Boltzmann Distribution and Effects on Rate6.3 Chemical Equilibrium0/06.3.1 Dynamic Equilibrium in Closed Systems6.3.2 Le Chatelier’s Principle: Qualitative Predictions6.3.3 Catalysts and Equilibrium Position6.3.4 Investigating Equilibrium Changes6.3.5 Industrial Compromises: Equilibrium and Rate6.3.6 Equilibrium Constant KC: Expressions and Uses6. Physical Chemistry6.1 Enthalpy Changes0/06.1.1 Exothermic and Endothermic Changes; Profiles6.1.2 Activation Energy and Energy Profiles6.1.3 Standard Conditions, States and Key Definitions6.1.4 Determining Enthalpy Changes Experimentally6.1.5 Average Bond Enthalpies and Calculations6.1.6 Hess’ Law and Enthalpy Cycles6.2 Reaction Rates0/06.2.1 Collision Theory and Concentration/Pressure Effects6.2.2 Catalysts and Alternative Pathways6.2.3 Catalysis and Sustainability Considerations6.2.4 Measuring Rates: Techniques and Procedures6.2.5 Boltzmann Distribution and Effects on Rate6.3 Chemical Equilibrium0/06.3.1 Dynamic Equilibrium in Closed Systems6.3.2 Le Chatelier’s Principle: Qualitative Predictions6.3.3 Catalysts and Equilibrium Position6.3.4 Investigating Equilibrium Changes6.3.5 Industrial Compromises: Equilibrium and Rate6.3.6 Equilibrium Constant KC: Expressions and Uses7. Basic Concepts and Hydrocarbons7.1 Basic Concepts of Organic Chemistry0/07.1.1 IUPAC Nomenclature Essentials7.1.2 Representing Organic Formulae7.1.3 Homologous Series and General Formulae7.1.4 Functional-Group and Structural Terms7.1.5 Structural Isomerism7.1.6 Bond Fission, Radicals and Curly Arrows7.2 Alkanes0/07.2.1 σ-bonds and Free Rotation in Alkanes7.2.2 Shapes and Bond Angles7.2.3 Boiling Point Trends7.2.4 Low Reactivity Explained7.2.5 Combustion of Alkanes7.2.6 Radical Substitution and its Limitations7.3 Alkenes0/07.3.1 π-Bonds, σ-Bonds and Restricted Rotation7.3.2 Stereoisomerism: E/Z and Cis–Trans7.3.3 Identifying Possible Stereoisomers7.3.4 Reactivity and Key Additions7.3.5 Electrophiles and Electrophilic Addition7.3.6 Polymers and Sustainability7. Basic Concepts and Hydrocarbons7.1 Basic Concepts of Organic Chemistry0/07.1.1 IUPAC Nomenclature Essentials7.1.2 Representing Organic Formulae7.1.3 Homologous Series and General Formulae7.1.4 Functional-Group and Structural Terms7.1.5 Structural Isomerism7.1.6 Bond Fission, Radicals and Curly Arrows7.2 Alkanes0/07.2.1 σ-bonds and Free Rotation in Alkanes7.2.2 Shapes and Bond Angles7.2.3 Boiling Point Trends7.2.4 Low Reactivity Explained7.2.5 Combustion of Alkanes7.2.6 Radical Substitution and its Limitations7.3 Alkenes0/07.3.1 π-Bonds, σ-Bonds and Restricted Rotation7.3.2 Stereoisomerism: E/Z and Cis–Trans7.3.3 Identifying Possible Stereoisomers7.3.4 Reactivity and Key Additions7.3.5 Electrophiles and Electrophilic Addition7.3.6 Polymers and Sustainability8. Alcohols, Haloalkanes and Analysis8.1 Alcohols0/08.1.1 Polarity, H-Bonding and Properties8.1.2 Primary, Secondary and Tertiary8.1.3 Combustion of Alcohols8.1.4 Oxidation: Aldehydes, Ketones and Acids8.1.5 Dehydration to Alkenes8.1.6 Substitution to Haloalkanes8.2 Haloalkanes0/08.2.1 Hydrolysis with Aqueous Alkali8.2.2 Hydrolysis with Water and AgNO38.2.3 Nucleophiles and Substitution Mechanism8.2.4 Rates and Bond Enthalpy Trend8.2.5 CFCs, Radicals and Ozone depletion8.2.6 Environmental Considerations8.3 Organic Synthesis0/08.3.1 Quickfit Apparatus and Reflux/Distillation8.3.2 Preparation and Purification of Liquids8.3.3 Identifying Functional Groups8.3.4 Predicting Properties and Reactions8.3.5 Devising Two‑Stage Routes8.3.6 Applying a Reaction Toolkit8.4 Analytical Techniques0/08.4.1 Infrared: Bond Vibrations and Peaks8.4.2 IR, Gases and Global Warming8.4.3 Using IR to Identify Functional Groups8.4.4 Interpreting Unfamiliar IR Spectra8.4.5 Mass Spectrometry: M+ and Fragments8.4.6 Combining Data to Deduce Structures8. Alcohols, Haloalkanes and Analysis8.1 Alcohols0/08.1.1 Polarity, H-Bonding and Properties8.1.2 Primary, Secondary and Tertiary8.1.3 Combustion of Alcohols8.1.4 Oxidation: Aldehydes, Ketones and Acids8.1.5 Dehydration to Alkenes8.1.6 Substitution to Haloalkanes8.2 Haloalkanes0/08.2.1 Hydrolysis with Aqueous Alkali8.2.2 Hydrolysis with Water and AgNO38.2.3 Nucleophiles and Substitution Mechanism8.2.4 Rates and Bond Enthalpy Trend8.2.5 CFCs, Radicals and Ozone depletion8.2.6 Environmental Considerations8.3 Organic Synthesis0/08.3.1 Quickfit Apparatus and Reflux/Distillation8.3.2 Preparation and Purification of Liquids8.3.3 Identifying Functional Groups8.3.4 Predicting Properties and Reactions8.3.5 Devising Two‑Stage Routes8.3.6 Applying a Reaction Toolkit8.4 Analytical Techniques0/08.4.1 Infrared: Bond Vibrations and Peaks8.4.2 IR, Gases and Global Warming8.4.3 Using IR to Identify Functional Groups8.4.4 Interpreting Unfamiliar IR Spectra8.4.5 Mass Spectrometry: M+ and Fragments8.4.6 Combining Data to Deduce Structures9. Rates, Equilibrium and pH9.1 How Fast?0/09.1.1 Rate Terms, Orders and Rate Equations9.1.2 Concentration–Time Graphs and Half-Life9.1.3 Rate–Concentration Graphs and Initial Rates9.1.4 Practical Methods for Measuring Rates9.1.5 Rate-Determining Step and Mechanisms9.1.6 Temperature and the Arrhenius Equation9.2 How Far?0/09.2.1 Mole Fraction and Partial Pressure9.2.2 Quantities at Equilibrium and Techniques9.2.3 Kc and Kp Expressions9.2.4 Calculating Kc, Kp and Units9.2.5 Effects on Equilibrium Constants9.2.6 Equilibrium Position and Control9.3 Acids, Bases and Buffers0/09.3.1 Brønsted–Lowry Acids, Bases and Conjugates9.3.2 Reactions of Acids with Metals and Bases9.3.3 Ka, pKa, pH and Kw Expressions9.3.4 pH Calculations: Strong Acids/Bases and Weak Acids9.3.5 Limits of Weak-Acid Approximations9.3.6 Buffers, Blood pH, Titration Curves and pH Meters9. Rates, Equilibrium and pH9.1 How Fast?0/09.1.1 Rate Terms, Orders and Rate Equations9.1.2 Concentration–Time Graphs and Half-Life9.1.3 Rate–Concentration Graphs and Initial Rates9.1.4 Practical Methods for Measuring Rates9.1.5 Rate-Determining Step and Mechanisms9.1.6 Temperature and the Arrhenius Equation9.2 How Far?0/09.2.1 Mole Fraction and Partial Pressure9.2.2 Quantities at Equilibrium and Techniques9.2.3 Kc and Kp Expressions9.2.4 Calculating Kc, Kp and Units9.2.5 Effects on Equilibrium Constants9.2.6 Equilibrium Position and Control9.3 Acids, Bases and Buffers0/09.3.1 Brønsted–Lowry Acids, Bases and Conjugates9.3.2 Reactions of Acids with Metals and Bases9.3.3 Ka, pKa, pH and Kw Expressions9.3.4 pH Calculations: Strong Acids/Bases and Weak Acids9.3.5 Limits of Weak-Acid Approximations9.3.6 Buffers, Blood pH, Titration Curves and pH Meters10. Energy10.1 Lattice Enthalpy0/010.1.1 Defining Lattice Enthalpy and Ionic Strength10.1.2 Born–Haber Cycles and Calculations10.1.3 Solution and Hydration Enthalpy Definitions10.1.4 Dissolving Cycles and Calculations10.1.5 Trends in Lattice and Hydration Enthalpies10.2 Enthalpy and Entropy0/010.2.1 Entropy as Energy Dispersal and Disorder10.2.2 Comparing Entropies of States and Gases10.2.3 Calculating Entropy Change for Reactions10.2.4 Free Energy and Feasibility10.2.5 Kinetic Limitations of ΔG Predictions10.3 Redox and Electrode Potentials0/010.3.1 Redox Terms and Balancing10.3.2 Predicting Electron-Transfer Reactions10.3.3 Redox Titration Techniques10.3.4 Redox Titration Calculations10.3.5 Standard Electrode Potentials and Cells10.3.6 Cell Potentials, Feasibility and Limitations10.3.7 Storage Cells and Fuel Cells10. Energy10.1 Lattice Enthalpy0/010.1.1 Defining Lattice Enthalpy and Ionic Strength10.1.2 Born–Haber Cycles and Calculations10.1.3 Solution and Hydration Enthalpy Definitions10.1.4 Dissolving Cycles and Calculations10.1.5 Trends in Lattice and Hydration Enthalpies10.2 Enthalpy and Entropy0/010.2.1 Entropy as Energy Dispersal and Disorder10.2.2 Comparing Entropies of States and Gases10.2.3 Calculating Entropy Change for Reactions10.2.4 Free Energy and Feasibility10.2.5 Kinetic Limitations of ΔG Predictions10.3 Redox and Electrode Potentials0/010.3.1 Redox Terms and Balancing10.3.2 Predicting Electron-Transfer Reactions10.3.3 Redox Titration Techniques10.3.4 Redox Titration Calculations10.3.5 Standard Electrode Potentials and Cells10.3.6 Cell Potentials, Feasibility and Limitations10.3.7 Storage Cells and Fuel Cells11. Transition Elements11.1 Transition Elements0/011.1.1 Electron Configurations of D-Block Elements11.1.2 What Makes a Transition Element?11.1.3 Characteristic Properties and Examples11.1.4 Ligands, Complexes and Coordination11.1.5 Stereoisomerism and Cis-Platin11.1.6 Ligand Substitution and Haemoglobin11.1.7 Precipitation Reactions and Complex Formation11.1.8 Redox Interconversions and Unfamiliar Reactions11.2 Qualitative Analysis0/011.2.1 Tests for Common Anions11.2.2 Tests for Ammonium and Transition-Metal Cations11. Transition Elements11.1 Transition Elements0/011.1.1 Electron Configurations of D-Block Elements11.1.2 What Makes a Transition Element?11.1.3 Characteristic Properties and Examples11.1.4 Ligands, Complexes and Coordination11.1.5 Stereoisomerism and Cis-Platin11.1.6 Ligand Substitution and Haemoglobin11.1.7 Precipitation Reactions and Complex Formation11.1.8 Redox Interconversions and Unfamiliar Reactions11.2 Qualitative Analysis0/011.2.1 Tests for Common Anions11.2.2 Tests for Ammonium and Transition-Metal Cations12. Aromatic Compounds, Carbonyls and Acids12.1 Aromatic Compounds0/012.1.1 Structure and Models of Benzene12.1.2 Experimental Evidence for Delocalisation12.1.3 Naming Substituted Aromatic Compounds12.1.4 Electrophilic Substitution Reactions of Arenes12.1.5 Mechanisms: Nitration and Halogenation12.1.6 Phenol: Acidity, Reactivity and Directing Effects12.2 Carbonyl Compounds0/012.2.1 Oxidation of Aldehydes12.2.2 Nucleophilic Addition: NaBH4 Reductions12.2.3 Nucleophilic Addition: HCN to Hydroxynitriles12.2.4 2,4‑DNP Test for Carbonyls12.2.5 Tollens’ Reagent and the Silver Mirror12.3 Carboxylic Acids and Esters0/012.3.1 Carboxylic Acids: Hydrogen Bonding and Solubility12.3.2 Reactions with Metals and Bases12.3.3 Making Esters: Acids and Anhydrides12.3.4 Hydrolysis of Esters: Acid Versus Alkali12.3.5 Preparing Acyl Chlorides from Acids12.3.6 Using Acyl Chlorides in Synthesis12. Aromatic Compounds, Carbonyls and Acids12.1 Aromatic Compounds0/012.1.1 Structure and Models of Benzene12.1.2 Experimental Evidence for Delocalisation12.1.3 Naming Substituted Aromatic Compounds12.1.4 Electrophilic Substitution Reactions of Arenes12.1.5 Mechanisms: Nitration and Halogenation12.1.6 Phenol: Acidity, Reactivity and Directing Effects12.2 Carbonyl Compounds0/012.2.1 Oxidation of Aldehydes12.2.2 Nucleophilic Addition: NaBH4 Reductions12.2.3 Nucleophilic Addition: HCN to Hydroxynitriles12.2.4 2,4‑DNP Test for Carbonyls12.2.5 Tollens’ Reagent and the Silver Mirror12.3 Carboxylic Acids and Esters0/012.3.1 Carboxylic Acids: Hydrogen Bonding and Solubility12.3.2 Reactions with Metals and Bases12.3.3 Making Esters: Acids and Anhydrides12.3.4 Hydrolysis of Esters: Acid Versus Alkali12.3.5 Preparing Acyl Chlorides from Acids12.3.6 Using Acyl Chlorides in Synthesis13. Nitrogen Compounds, Polymers and Synthesis13.1 Amines0/013.1.1 Basicity and Salt Formation13.1.2 Making Aliphatic Amines from Haloalkanes13.1.3 Making Aromatic Amines from Nitroarenes13.2 Amino Acids, Amides and Chirality0/013.2.1 α‑Amino Acid Functional Groups and Reactions13.2.2 Primary and Secondary Amides13.2.3 Optical Isomerism and Chiral Centres13.3 Polyesters and Polyamides0/013.3.1 Making Polyesters by Condensation13.3.2 Making Polyamides by Condensation13.3.3 Hydrolysing Polyesters13.3.4 Hydrolysing Polyamides13.3.5 Predicting Repeat Units from Monomers13.3.6 Finding Monomers from Polymer Structure13.4 Carbon–Carbon Bond Formation0/013.4.1 Extending Carbon Chains by C–C bond Formation13.4.2 Haloalkanes with Cyanide: Substitution Mechanism13.4.3 Carbonyls with HCN: Addition Mechanism13.4.4 Transforming Nitriles: Reduction to Amines13.4.5 Transforming Nitriles: Acid Hydrolysis to Acids13.4.6 Friedel–Crafts Alkylation and Acylation13.5 Organic Synthesis0/013.5.1 Organic Preparation Techniques13.5.2 Purifying Organic Solids13.5.3 Identifying Functional Groups and Properties13.5.4 Designing Multi‑Stage Synthetic Routes13. Nitrogen Compounds, Polymers and Synthesis13.1 Amines0/013.1.1 Basicity and Salt Formation13.1.2 Making Aliphatic Amines from Haloalkanes13.1.3 Making Aromatic Amines from Nitroarenes13.2 Amino Acids, Amides and Chirality0/013.2.1 α‑Amino Acid Functional Groups and Reactions13.2.2 Primary and Secondary Amides13.2.3 Optical Isomerism and Chiral Centres13.3 Polyesters and Polyamides0/013.3.1 Making Polyesters by Condensation13.3.2 Making Polyamides by Condensation13.3.3 Hydrolysing Polyesters13.3.4 Hydrolysing Polyamides13.3.5 Predicting Repeat Units from Monomers13.3.6 Finding Monomers from Polymer Structure13.4 Carbon–Carbon Bond Formation0/013.4.1 Extending Carbon Chains by C–C bond Formation13.4.2 Haloalkanes with Cyanide: Substitution Mechanism13.4.3 Carbonyls with HCN: Addition Mechanism13.4.4 Transforming Nitriles: Reduction to Amines13.4.5 Transforming Nitriles: Acid Hydrolysis to Acids13.4.6 Friedel–Crafts Alkylation and Acylation13.5 Organic Synthesis0/013.5.1 Organic Preparation Techniques13.5.2 Purifying Organic Solids13.5.3 Identifying Functional Groups and Properties13.5.4 Designing Multi‑Stage Synthetic Routes14. Analysis14.1 Chromatography and Qualitative Analysis0/014.1.1 Thin-Layer Chromatography and Rf Values14.1.2 Gas Chromatography: Retention Times14.1.3 Gas Chromatography: Quantification14.1.4 Test‑Tube Reactions: Alkenes and Haloalkanes14.1.5 Test‑Tube Reactions: Phenols and Carboxylic Acids14.1.6 Test‑Tube Reactions: Carbonyls and Alcohols/Aldehydes14.2 Spectroscopy0/014.2.1 Carbon‑13 NMR Analysis14.2.2 Proton NMR: Environments and Integration14.2.3 Proton NMR: Splitting and Aromatic Protons14.2.4 Predicting NMR Spectra14.2.5 NMR Standards and Solvents14.2.6 Combining Evidence to Deduce Structures14. Analysis14.1 Chromatography and Qualitative Analysis0/014.1.1 Thin-Layer Chromatography and Rf Values14.1.2 Gas Chromatography: Retention Times14.1.3 Gas Chromatography: Quantification14.1.4 Test‑Tube Reactions: Alkenes and Haloalkanes14.1.5 Test‑Tube Reactions: Phenols and Carboxylic Acids14.1.6 Test‑Tube Reactions: Carbonyls and Alcohols/Aldehydes14.2 Spectroscopy0/014.2.1 Carbon‑13 NMR Analysis14.2.2 Proton NMR: Environments and Integration14.2.3 Proton NMR: Splitting and Aromatic Protons14.2.4 Predicting NMR Spectra14.2.5 NMR Standards and Solvents14.2.6 Combining Evidence to Deduce Structures