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DP IB Chemistry: HL

Revision Notes

Home / IB / Chemistry: HL / DP / Revision Notes / 10. Organic Chemistry / 10.2 Functional Group Chemistry / 10.2.2 Alkanes - Halogenation


10.2.2 Alkanes - Halogenation


Halogenation of Alkanes

 Free-radical substitution of alkanes

  • Alkanes can undergo free-radical substitution in which a hydrogen atom gets substituted by a halogen (chlorine/bromine)
  • Since alkanes are very unreactive, ultraviolet light (sunlight) is needed for this substitution reaction to occur
  • The free-radical substitution reaction consists of three steps:
    • In the initiation step, the halogen bond (Cl-Cl or Br-Br) is broken by UV energy to form two radicals
    • These radicals create further radicals in a chain type reaction called the propagation step
    • The reaction is terminated when two radicals collide with each other in a termination step

Hydrocarbons Colour Change of Solution, downloadable AS & A Level Chemistry revision notes

The fact that the bromine colour has disappeared only when mixed with an alkane and placed in sunlight suggests that the ultraviolet light is essential for the free radical substitution reaction to take place

Initiation step

  • In the initiation step the Cl-Cl or Br-Br is broken by energy from the UV light
  • This produces two radicals in a homolytic fission reaction

Hydrocarbons Initiation Step, downloadable AS & A Level Chemistry revision notes

The first step of the free-radical substitution reaction is the initiation step in which two free radicals are formed by sunlight

Propagation step

  • The propagation step refers to the progression (growing) of the substitution reaction in a chain type reaction
    • Free radicals are very reactive and will attack the unreactive alkanes
    • A C-H bond breaks homolytically (each atom gets an electron from the covalent bond)
    • An alkyl free radical is produced
    • This can attack another chlorine/bromine molecule to form the halogenoalkane and regenerate the chlorine/bromine free radical
    • This free radical can then repeat the cycle

Hydrocarbons Propagation Step, downloadable AS & A Level Chemistry revision notes

The second step of the free-radical substitution reaction is the propagation step in which the reaction grows in a chain type reaction

    • This reaction is not very suitable for preparing specific halogenoalkanes as a mixture of substitution products are formed
    • If there is enough chlorine/bromine present, all the hydrogens in the alkane will eventually get substituted (eg. ethane will become C2Cl6/C2Br6)

Hydrocarbons Side-Products, downloadable AS & A Level Chemistry revision notes

The free-radical substitution reaction gives a variety of products and not a pure halogenoalkane

Termination step

  • The termination step is when the chain reaction terminates (stops) due to two free radicals reacting together and forming a single unreactive molecule
    • Multiple products are possible
 Hydrocarbons Termination Step, downloadable AS & A Level Chemistry revision notes

The final step in the substitution reaction to form a single unreactive molecule

Exam Tip

Make sure you practice and are able to write out these equations, especially the propagation steps which students frequently get wrong.It is quite common for students to incorrectly show a hydrogen radical produced in propagation, which does not happen:

CH3CH3+ Cl· →   CH3CH2 Cl    +   H·

Do not fall into this trap!


  • 1. Stoichiometric Relationships
    • 1.1 Matter, Chemical Change & the Mole Concept
      • 1.1.1 Elements, Compounds & Mixtures
        • 1.1.2 Equations
          • 1.1.3 State Changes
            • 1.1.4 The Mole Concept
              • 1.1.5 Moles-Mass Problems
                • 1.1.6 Empirical Formulae
                • 1.2 Reacting Masses & Volumes
                  • 1.2.1 Reacting Masses
                    • 1.2.2 Reaction Yields
                      • 1.2.3 Avogadro's Law & Molar Gas Volume
                        • 1.2.4 The Ideal Gas Equation
                          • 1.2.5 Gas Law Relationships
                            • 1.2.6 Real Gases
                              • 1.2.7 Standard Solutions
                                • 1.2.8 Concentration Calculations
                                  • 1.2.9 Titrations
                                • 2. Atomic Structure
                                  • 2.1 Atomic & Electronic Structure
                                    • 2.1.1 The Nuclear Atom
                                      • 2.1.2 Deducing Subatomic Particles
                                        • 2.1.3 Relative Atomic Mass Calculations
                                          • 2.1.4 The Electromagnetic Spectrum
                                            • 2.1.5 Emission Spectra
                                              • 2.1.6 Energy Levels & Sublevels
                                                • 2.1.7 Sublevels & Orbitals
                                                  • 2.1.8 Writing Electron Configurations
                                                • 3. Periodicity
                                                  • 3.1 The Periodic Table & Periodic Trends
                                                    • 3.1.1 The Periodic Table
                                                      • 3.1.2 Periodic Trends: Physical - Atomic & Ionic Radius
                                                        • 3.1.3 Periodic Trends: Physical - Ionisation Energy
                                                          • 3.1.4 Periodic Trends: Physical - Electron Affinity
                                                            • 3.1.5 Periodic Trends: Physical - Electronegativity
                                                              • 3.1.6 Periodic Trends: Chemical
                                                              • 3.2 Oxides, Group 1 & Group 17
                                                                • 3.2.1 Periodic Trends: Oxides Across a Period
                                                                  • 3.2.2 Periodic Trends: Group 1 - The Alkali Metals
                                                                    • 3.2.3 Periodic Trends: Group 17 - The Halogens
                                                                  • 4. Chemical Bonding & Structure
                                                                    • 4.1 Ionic & Covalent Bonding
                                                                      • 4.1.1 Forming Ions
                                                                        • 4.1.2 Ionic Compounds
                                                                          • 4.1.3 Formulae & Names of Ionic Compounds
                                                                            • 4.1.4 Covalent Bonds
                                                                              • 4.1.5 Bond Polarity
                                                                                • 4.1.6 Lewis Structures
                                                                                • 4.2 Resonance, Shapes & Giant Structures
                                                                                  • 4.2.1 Resonance Structures
                                                                                    • 4.2.2 Shapes of Molecules
                                                                                      • 4.2.3 Predicting Molecular Shapes
                                                                                        • 4.2.4 Molecular Polarity
                                                                                          • 4.2.5 Giant Covalent Structures
                                                                                          • 4.3 Intermolecular Forces & Metallic Bonding
                                                                                            • 4.3.1 Types of Intermolecular Forces
                                                                                              • 4.3.2 Deducing Intermolecular Forces
                                                                                                • 4.3.3 Properties of Covalent Compounds
                                                                                                  • 4.3.4 Metallic Bonding
                                                                                                    • 4.3.5 Trends in Melting Points of Metals
                                                                                                      • 4.3.6 Alloys & their Properties
                                                                                                    • 5. Energetics/ Thermochemistry
                                                                                                      • 5.1 Energetics
                                                                                                        • 5.1.1 Energy Changes in Reactions
                                                                                                          • 5.1.2 Standard Enthalpy Change
                                                                                                            • 5.1.3 Calorimetry
                                                                                                              • 5.1.4 Calorimetry Experiments
                                                                                                              • 5.2 Hess's Law
                                                                                                                • 5.2.1 Hess's Law
                                                                                                                  • 5.2.2 Using Hess's Law - Cycles
                                                                                                                    • 5.2.3 Using Hess's Law - Equations
                                                                                                                      • 5.2.4 Using ∆Hf° to Find Enthalpy Changes
                                                                                                                      • 5.3 Bond Enthalpy
                                                                                                                        • 5.3.1 Bond Enthalpy
                                                                                                                          • 5.3.2 Bond Enthalpy Calculations
                                                                                                                            • 5.3.3 Energy Profiles
                                                                                                                              • 5.3.4 Case Study: Ozone
                                                                                                                            • 6. Chemical Kinetics
                                                                                                                              • 6.1 Chemical Kinetics
                                                                                                                                • 6.1.1 Collision Theory
                                                                                                                                  • 6.1.2 Rate of Reaction
                                                                                                                                    • 6.1.3 Measuring Rates
                                                                                                                                      • 6.1.4 Activation Energy
                                                                                                                                        • 6.1.5 Rate Experiments
                                                                                                                                          • 6.1.6 Explaining Rates
                                                                                                                                            • 6.1.7 Maxwell-Boltzmann Curves
                                                                                                                                              • 6.1.8 Energy Profiles & Catalysis
                                                                                                                                            • 7. Equilibrium
                                                                                                                                              • 7.1 Equilibrium
                                                                                                                                                • 7.1.1 The State of Equilibrium
                                                                                                                                                  • 7.1.2 The Equilibrium Law
                                                                                                                                                    • 7.1.3 Equilibrium Constant Relationships
                                                                                                                                                      • 7.1.4 The Reaction Quotient
                                                                                                                                                        • 7.1.5 Le Chatelier's Principle
                                                                                                                                                          • 7.1.6 Catalysts & Equilibrium
                                                                                                                                                        • 8. Acids & Bases
                                                                                                                                                          • 8.1 Theories & Reactions of Acids & Bases
                                                                                                                                                            • 8.1.1 Brønsted–Lowry Acids & Bases
                                                                                                                                                              • 8.1.2 Conjugate Acid-Base Pairs
                                                                                                                                                                • 8.1.3 Characteristic Reactions of Acids
                                                                                                                                                                  • 8.1.4 Neutralization
                                                                                                                                                                  • 8.2 More About Acids
                                                                                                                                                                    • 8.2.1 Acid-base Titrations
                                                                                                                                                                      • 8.2.2 pH & [H⁺]
                                                                                                                                                                        • 8.2.3 Interpreting pH
                                                                                                                                                                          • 8.2.4 The Ionic Product of Water
                                                                                                                                                                            • 8.2.5 Acid-Base Calculations
                                                                                                                                                                              • 8.2.6 pH Meters & Universal Indicator
                                                                                                                                                                                • 8.2.7 Strong & Weak Acids & Bases
                                                                                                                                                                                  • 8.2.8 Comparing Strong & Weak Acids
                                                                                                                                                                                  • 8.3 Acid Deposition
                                                                                                                                                                                    • 8.3.1 Acid Deposition
                                                                                                                                                                                      • 8.3.2 Effects of Acid Deposition
                                                                                                                                                                                        • 8.3.3 Reducing Sulfur Oxide Emissions
                                                                                                                                                                                      • 9. Redox Processes
                                                                                                                                                                                        • 9.1 Redox Processes
                                                                                                                                                                                          • 9.1.1 Oxidation & reduction
                                                                                                                                                                                            • 9.1.2 Deducing Oxidation Numbers
                                                                                                                                                                                              • 9.1.3 Oxidizing & Reducing agents
                                                                                                                                                                                                • 9.1.4 Naming Transition Metal Compounds
                                                                                                                                                                                                  • 9.1.5 Half Equations
                                                                                                                                                                                                    • 9.1.6 The Activity Series
                                                                                                                                                                                                      • 9.1.7 Redox Titrations
                                                                                                                                                                                                        • 9.1.8 The Winkler Method
                                                                                                                                                                                                          • 9.1.9 Voltaic Cells
                                                                                                                                                                                                            • 9.1.10 Electrolytic Cells
                                                                                                                                                                                                          • 10. Organic Chemistry
                                                                                                                                                                                                            • 10.1 Fundamentals of Organic Chemistry
                                                                                                                                                                                                              • 10.1.1 Homologous Series
                                                                                                                                                                                                                • 10.1.2 Understanding Organic Molecules
                                                                                                                                                                                                                  • 10.1.3 Nomenclature
                                                                                                                                                                                                                    • 10.1.4 Organic Families - Hydrocarbons
                                                                                                                                                                                                                      • 10.1.5 Organic Families - Halogenoalkanes
                                                                                                                                                                                                                        • 10.1.6 Organic Families - Alcohols & Ethers
                                                                                                                                                                                                                          • 10.1.7 Organic Families - Carbonyls
                                                                                                                                                                                                                            • 10.1.8 Organic Families - Carboxylic Acids & Esters
                                                                                                                                                                                                                              • 10.1.9 Organic Families - Organic Nitrogen Compounds
                                                                                                                                                                                                                                • 10.1.10 3-D modelling
                                                                                                                                                                                                                                  • 10.1.11 Primary, Secondary & Tertiary atoms
                                                                                                                                                                                                                                    • 10.1.12 Benzene
                                                                                                                                                                                                                                    • 10.2 Functional Group Chemistry
                                                                                                                                                                                                                                      • 10.2.1 Alkanes - Combustion
                                                                                                                                                                                                                                        • 10.2.2 Alkanes - Halogenation
                                                                                                                                                                                                                                          • 10.2.3 Alkenes - Reactivity
                                                                                                                                                                                                                                            • 10.2.4 Alkenes - Hydrogenation
                                                                                                                                                                                                                                              • 10.2.5 Alkenes - Halogenation
                                                                                                                                                                                                                                                • 10.2.6 Alkenes - Hydrohalogenation
                                                                                                                                                                                                                                                  • 10.2.7 Alkenes - Hydration
                                                                                                                                                                                                                                                    • 10.2.8 Addition Polymers
                                                                                                                                                                                                                                                      • 10.2.9 Alcohols - Combustion
                                                                                                                                                                                                                                                        • 10.2.10 Alcohols - Oxidation
                                                                                                                                                                                                                                                          • 10.2.11 Alcohols - Esterification
                                                                                                                                                                                                                                                            • 10.2.12 Halogenoalkanes
                                                                                                                                                                                                                                                              • 10.2.13 Reactions of Benzene
                                                                                                                                                                                                                                                            • 11. Measurements & Data Processes
                                                                                                                                                                                                                                                              • 11.1 Spectroscopic Identification
                                                                                                                                                                                                                                                                • 11.1.1 Index of Hydrogen Deficiency
                                                                                                                                                                                                                                                                  • 11.1.2 Mass Spectrometry
                                                                                                                                                                                                                                                                    • 11.1.3 Nuclear Magnetic Resonance Spectroscopy
                                                                                                                                                                                                                                                                      • 11.1.4 Infrared Spectroscopy
                                                                                                                                                                                                                                                                      • 11.2 Synoptic Data Handling & Graphical Skills
                                                                                                                                                                                                                                                                        • 11.2.1 Recording Data
                                                                                                                                                                                                                                                                          • 11.2.2 Processing Errors
                                                                                                                                                                                                                                                                            • 11.2.3 Reducing the Impact of Errors
                                                                                                                                                                                                                                                                              • 11.2.4 Percentage Error
                                                                                                                                                                                                                                                                                • 11.2.5 Drawing Graphs
                                                                                                                                                                                                                                                                                  • 11.2.6 Analysing Graphs
                                                                                                                                                                                                                                                                                • 12. HL Atomic Structure
                                                                                                                                                                                                                                                                                  • 12.1 Electrons in Atoms
                                                                                                                                                                                                                                                                                    • 12.1.1 Emission Spectra & First Ionisation Energy
                                                                                                                                                                                                                                                                                      • 12.1.2 Ionisation Energy Trends
                                                                                                                                                                                                                                                                                    • 13. HL The Periodic Table- Transition Metals
                                                                                                                                                                                                                                                                                      • 13.1 Transition Metals
                                                                                                                                                                                                                                                                                        • 13.1.1 Transition Elements
                                                                                                                                                                                                                                                                                          • 13.1.2 Variable Oxidation States
                                                                                                                                                                                                                                                                                            • 13.1.3 Complex Ions
                                                                                                                                                                                                                                                                                              • 13.1.4 Catalytic & Magnetic Properties
                                                                                                                                                                                                                                                                                                • 13.1.5 Colour in Transition Metals
                                                                                                                                                                                                                                                                                                  • 13.1.6 Factors Affecting Colour
                                                                                                                                                                                                                                                                                                • 14. HL Chemical Bonding & Structure
                                                                                                                                                                                                                                                                                                  • 14.1 More Structures & Shapes
                                                                                                                                                                                                                                                                                                    • 14.1.1 Covalent Bonds
                                                                                                                                                                                                                                                                                                      • 14.1.2 More Lewis Structures
                                                                                                                                                                                                                                                                                                        • 14.1.3 Further VSEPR Theory
                                                                                                                                                                                                                                                                                                          • 14.1.4 Formal Charge
                                                                                                                                                                                                                                                                                                          • 14.2 Further Aspects of Bonding
                                                                                                                                                                                                                                                                                                            • 14.2.1 Delocalisation & Resonance
                                                                                                                                                                                                                                                                                                              • 14.2.2 Ozone Revisited
                                                                                                                                                                                                                                                                                                                • 14.2.3 Hybrid Orbitals
                                                                                                                                                                                                                                                                                                              • 15. HL Energetics / Thermochemistry
                                                                                                                                                                                                                                                                                                                • 15.1 Energy Cycles
                                                                                                                                                                                                                                                                                                                  • 15.1.1 Key Enthalpy Terms
                                                                                                                                                                                                                                                                                                                    • 15.1.2 Born-Haber Cycles
                                                                                                                                                                                                                                                                                                                      • 15.1.3 Born-Haber Cycle Calculations
                                                                                                                                                                                                                                                                                                                        • 15.1.4 Dissolution Energy Cycles
                                                                                                                                                                                                                                                                                                                          • 15.1.5 Energy Changes in Aqueous Solutions
                                                                                                                                                                                                                                                                                                                          • 15.2 Entropy & Spontaneity
                                                                                                                                                                                                                                                                                                                            • 15.2.1 Entropy
                                                                                                                                                                                                                                                                                                                              • 15.2.2 Calculating Entropy Change
                                                                                                                                                                                                                                                                                                                                • 15.2.3 Gibbs Free Energy
                                                                                                                                                                                                                                                                                                                                  • 15.2.4 Spontaneous Reactions
                                                                                                                                                                                                                                                                                                                                    • 15.2.5 Free Energy & Equilibrium
                                                                                                                                                                                                                                                                                                                                  • 16. HL Chemical Kinetics
                                                                                                                                                                                                                                                                                                                                    • 16.1 Rate Expression & Reaction Mechanism
                                                                                                                                                                                                                                                                                                                                      • 16.1.1 Rate Equations
                                                                                                                                                                                                                                                                                                                                        • 16.1.2 Rate Constants
                                                                                                                                                                                                                                                                                                                                          • 16.1.3 Graphical Representations
                                                                                                                                                                                                                                                                                                                                            • 16.1.4 Rate Determining Step
                                                                                                                                                                                                                                                                                                                                              • 16.1.5 Mechanism Problems
                                                                                                                                                                                                                                                                                                                                              • 16.2 Activation Energy
                                                                                                                                                                                                                                                                                                                                                • 16.2.1 The Arrhenius Equation
                                                                                                                                                                                                                                                                                                                                                  • 16.2.2 Graphing the Arrhenius Equation
                                                                                                                                                                                                                                                                                                                                                    • 16.2.3 Activation Energy from Rate Constants
                                                                                                                                                                                                                                                                                                                                                  • 17. HL Equilibrium
                                                                                                                                                                                                                                                                                                                                                    • 17.1 The Equilibrium Law
                                                                                                                                                                                                                                                                                                                                                      • 17.1.1 Applying the Equilibrium Law
                                                                                                                                                                                                                                                                                                                                                        • 17.1.2 Gibbs Free Energy & the Equilibrium Constant
                                                                                                                                                                                                                                                                                                                                                      • 18. HL Acids & Bases
                                                                                                                                                                                                                                                                                                                                                        • 18.1 Further Aspects of Acids & Bases
                                                                                                                                                                                                                                                                                                                                                          • 18.1.1 Lewis Theory
                                                                                                                                                                                                                                                                                                                                                            • 18.1.2 pH Curves
                                                                                                                                                                                                                                                                                                                                                              • 18.1.3 Indicators
                                                                                                                                                                                                                                                                                                                                                                • 18.1.4 Buffers
                                                                                                                                                                                                                                                                                                                                                                  • 18.1.5 Salt Hydrolysis
                                                                                                                                                                                                                                                                                                                                                                  • 18.2 Calculations Involving Acids & Bases
                                                                                                                                                                                                                                                                                                                                                                    • 18.2.1 Acid & Base Dissociation Constants
                                                                                                                                                                                                                                                                                                                                                                      • 18.2.2 Acid & Base Problem Solving
                                                                                                                                                                                                                                                                                                                                                                    • 19. HL Redox Processes
                                                                                                                                                                                                                                                                                                                                                                      • 19.1 Electrochemical Cells
                                                                                                                                                                                                                                                                                                                                                                        • 19.1.1 Electrochemical Cells
                                                                                                                                                                                                                                                                                                                                                                          • 19.1.2 The Standard Hydrogen Electrode
                                                                                                                                                                                                                                                                                                                                                                            • 19.1.3 Electrolysis of Aqueous Solutions
                                                                                                                                                                                                                                                                                                                                                                              • 19.1.4 Quantitative Electrolysis
                                                                                                                                                                                                                                                                                                                                                                                • 19.1.5 Free Energy & Eº
                                                                                                                                                                                                                                                                                                                                                                                  • 19.1.6 Electroplating
                                                                                                                                                                                                                                                                                                                                                                                • 20. HL Organic Chemistry
                                                                                                                                                                                                                                                                                                                                                                                  • 20.1 Types of Organic Reactions
                                                                                                                                                                                                                                                                                                                                                                                    • 20.1.1 Nucleophilic Substitution Reactions
                                                                                                                                                                                                                                                                                                                                                                                      • 20.1.2 Electrophilic Addition Reactions
                                                                                                                                                                                                                                                                                                                                                                                        • 20.1.3 Electrophilic Substitution Reactions
                                                                                                                                                                                                                                                                                                                                                                                          • 20.1.4 Reduction Reactions
                                                                                                                                                                                                                                                                                                                                                                                          • 20.2 Synthetic Routes
                                                                                                                                                                                                                                                                                                                                                                                            • 20.2.1 Synthesis
                                                                                                                                                                                                                                                                                                                                                                                            • 20.3 Stereoisomerism
                                                                                                                                                                                                                                                                                                                                                                                              • 20.3.1 Stereoisomers
                                                                                                                                                                                                                                                                                                                                                                                                • 20.3.2 Cis-Trans & E/Z Isomers
                                                                                                                                                                                                                                                                                                                                                                                                  • 20.3.3 Optical Isomers
                                                                                                                                                                                                                                                                                                                                                                                                • 21. Measurement & Analysis
                                                                                                                                                                                                                                                                                                                                                                                                  • 21.1 Spectroscopic Identification of Organic compounds
                                                                                                                                                                                                                                                                                                                                                                                                    • 21.1.1 High Resolution NMR
                                                                                                                                                                                                                                                                                                                                                                                                      • 21.1.2 X-Ray Crystallography
                                                                                                                                                                                                                                                                                                                                                                                                        • 21.1.3 Structure Identification Problems
                                                                                                                                                                                                                                                                                                                                                                                                      Stewart Hird

                                                                                                                                                                                                                                                                                                                                                                                                      Author: Stewart

                                                                                                                                                                                                                                                                                                                                                                                                      Stewart has been an enthusiastic GCSE, A Level and IB Chemistry teacher for more than 30 years in the UK as well as overseas, and has been an examiner for IB and A Level, also. As a long-standing Head of Department, Stewart brings a wealth of experience to creating Topic Questions and revision materials for Save My Exams.


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