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Edexcel A Level Chemistry

Revision Notes

Home / A Level / Chemistry / Edexcel / Revision Notes / 7. Advanced Organic Chemistry (A Level Only) / 7.4 Organic Chemistry III: Aromatic Chemistry / 7.4.1 Benzene Structure


7.4.1 Benzene Structure


Models of Benzene

Structure of Benzene

  • The structure of benzene was determined many years ago, by a chemist called Kekule
  • The structure consists of 6 carbon atoms in a hexagonal ring, with alternating single and double carbon-carbon bonds
    • This suggests that benzene should react in the same way that an unsaturated alkene does
    • However, this is not the case

Structure of benzene, downloadable AS & A Level Chemistry revision notes

Like other aromatic compounds, benzene has a planar structure due to the sp2 hybridisation of carbon atoms and the conjugated π system in the ring

  • Each carbon atom in the ring forms three σ bonds using the sp2 orbitals
  • The remaining p orbitals overlap laterally with p orbitals of neighbouring carbon atoms to form a π system
  • This extensive sideways overlap of p orbitals results in the electrons being delocalised and able to freely spread over the entire ring causing a π system
    • The π system is made up of two ring shaped clouds of electron density - one above the plane and one below it

  • Benzene and other aromatic compounds are regular and planar compounds with bond angles of 120 o
  • The delocalisation of electrons means that all of the carbon-carbon bonds in these compounds are identical and have both single and double bond character
  • The bonds all being the same length is evidence for the delocalised ring structure of benzene

Evidence for delocalisation

  • This evidence of the bonding in benzene is provided by data from enthalpy changes of hydrogenation and carbon-carbon bond lengths
  • Hydrogenation of cyclohexene
    • Each molecule has one C=C double bond
    • The enthalpy change for the reaction of cyclohexene is -120 kJ mol-1

C6H10 + H2 → C6H12   ΔHΘ = -120 kJ mol-1

  • Hydrogenation of beznene
    • The Kekule structure of benzene as cyclohexa-1,3,5-triene has three double C=C bonds
    • It would be expected that the enthalpy change for the hydrogenation of this structure would be three times the enthalpy change for the one C=C bond in cyclohexene 

C6H6 + 3H2 → C6H12   ΔHΘ = 3 x -120 kJ mol-1 = -360 kJ mol-1

  • When benzene is reacted with hydrogen, the enthalpy change obtained is actually far less exothermic, ΔHΘ = -208 kJ mol-1

Resistance to Bromination

  • Alkenes tend to undergo bromination easily which can be observed in cyclohexene

C6H10 + Br2 → C6H10Br2 

  • As the π bond contains localised electrons, it produces an area of high electron density allowing it to repel the electron in the bromine molecule
  • Therefore a dipole is introduced making one bromine atom δ+ and one δ- bromine atom 
  • The δ+ bromine is attracted to the π bond in the cyclohexane 
  • This then leaves a carbocation in the intermediate molecule which the negative bromide ion is attracted to, hence forming 1,2-dibromocyclohexane by electrophilic addition
  • In benzene, there are no localised areas of high electron density, preventing it from being able to polarise the bromine moelcule 
  • In order for benzene to undergo electrophilic substitution with bromine, a halogen carrier must be present in the reaction e.g. AlBr3



  • 1. Physical Chemistry
    • 1.1 Atomic Structure
      • 1.1.1 Structure of the Atom
        • 1.1.2 Isotopes
          • 1.1.3 Relative Mass
            • 1.1.4 Mass Spectrometry
            • 1.2 Ions & Electrons
              • 1.2.1 Ionisation Energy
                • 1.2.2 Quantum Shells
                  • 1.2.3 Orbitals
                    • 1.2.4 Electronic Configurations
                    • 1.3 The Periodic Table
                      • 1.3.1 Periodicity
                      • 1.4 Bonding
                        • 1.4.1 Ionic Bonding Overview
                          • 1.4.2 Representing Ionic Bonding
                            • 1.4.3 Ionic Trends
                              • 1.4.4 Physical Properties of Ionic Compounds
                                • 1.4.5 Covalent Bonding Overview
                                  • 1.4.6 Covalent Dot-and-Cross Diagrams
                                    • 1.4.7 Bond Length & Bond Strength
                                      • 1.4.8 Shapes of Covalent Compounds
                                      • 1.5 Structure
                                        • 1.5.1 Electronegativity
                                          • 1.5.2 Intermolecular Forces
                                            • 1.5.3 Hydrogen Bonding
                                              • 1.5.4 Intermolecular Forces & Physical Properties
                                                • 1.5.5 Metallic Bonding
                                                  • 1.5.6 Giant Lattices
                                                    • 1.5.7 Covalent Structures
                                                      • 1.5.8 Predicting Structures
                                                      • 1.6 Formulae, Equations & Avogadro
                                                        • 1.6.1 Empirical & Molecular Formulae
                                                          • 1.6.2 Balanced Equations
                                                            • 1.6.3 Applying Equations
                                                              • 1.6.4 The Mole & the Avogadro Constant
                                                                • 1.6.5 Amount of Substance Calculations
                                                                • 1.7 Reaction Calculations
                                                                  • 1.7.1 Reacting Volume Calculations
                                                                    • 1.7.2 Titrations
                                                                      • 1.7.3 Error & Uncertainty
                                                                        • 1.7.4 Yield & Atom Economy
                                                                        • 1.8 Energetics I
                                                                          • 1.8.1 Enthalpy Changes
                                                                            • 1.8.2 Enthalpy Level Diagrams
                                                                              • 1.8.3 Calorimetry
                                                                                • 1.8.4 Hess Cycles
                                                                                  • 1.8.5 Bond Enthalpy
                                                                                  • 1.9 Kinetics I
                                                                                    • 1.9.1 Collision Theory & Rates
                                                                                      • 1.9.2 Calculating Rates of Reaction
                                                                                        • 1.9.3 Maxwell-Boltzmann Distributions
                                                                                          • 1.9.4 Catalysts in Industry
                                                                                          • 1.10 Equilibrium I
                                                                                            • 1.10.1 Dynamic Equilibrium
                                                                                              • 1.10.2 Le Chatelier's Principle
                                                                                                • 1.10.3 The Rate & Yield Compromise
                                                                                                  • 1.10.4 Deducing Kc Expressions
                                                                                                • 2. Inorganic Chemistry
                                                                                                  • 2.1 Redox I
                                                                                                    • 2.1.1 Oxidation Number
                                                                                                      • 2.1.2 Types of Reduction & Oxidation
                                                                                                        • 2.1.3 Redox & Disproportionation
                                                                                                          • 2.1.4 Ionic Equations
                                                                                                          • 2.2 Groups 1 & 2
                                                                                                            • 2.2.1 Explaining Group 2 Trends
                                                                                                              • 2.2.2 Reactions of Group 2
                                                                                                                • 2.2.3 Group 2 Hydroxides & Sulfates
                                                                                                                  • 2.2.4 Group 2 Carbonates & Nitrates
                                                                                                                    • 2.2.5 Flame Tests
                                                                                                                    • 2.3 Group 7
                                                                                                                      • 2.3.1 Group 7 Trends
                                                                                                                        • 2.3.2 Halogen Displacement Reactions
                                                                                                                          • 2.3.3 Halogen Redox Reactions
                                                                                                                            • 2.3.4 Halide Ion Reactions
                                                                                                                          • 3. Organic Chemistry
                                                                                                                            • 3.1 Introduction to Organic Chemistry
                                                                                                                              • 3.1.1 Formulae of Organic Compounds
                                                                                                                                • 3.1.2 Homologous Series & Functional Groups
                                                                                                                                  • 3.1.3 Nomenclature & Classification
                                                                                                                                    • 3.1.4 Structural Isomerism
                                                                                                                                      • 3.1.5 Stereoisomerism
                                                                                                                                      • 3.2 Alkanes
                                                                                                                                        • 3.2.1 Describing Alkanes
                                                                                                                                          • 3.2.2 Alkane Fuels
                                                                                                                                            • 3.2.3 Pollution from Combustion
                                                                                                                                              • 3.2.4 Reducing Pollution
                                                                                                                                                • 3.2.5 Free Radicals
                                                                                                                                                • 3.3 Alkenes
                                                                                                                                                  • 3.3.1 Describing Alkenes
                                                                                                                                                    • 3.3.2 Bonding in Alkenes
                                                                                                                                                      • 3.3.3 Electrophilic Addition
                                                                                                                                                        • 3.3.4 Electrophilic Addition Mechanism
                                                                                                                                                          • 3.3.5 Saturation Test
                                                                                                                                                            • 3.3.6 Addition Polymerisation
                                                                                                                                                              • 3.3.7 Waste Polymers
                                                                                                                                                              • 3.4 Halogenoalkanes
                                                                                                                                                                • 3.4.1 Classifying Halogenoalkanes
                                                                                                                                                                  • 3.4.2 Nucleophilic Substitution
                                                                                                                                                                    • 3.4.3 Nucleophilic Substitution Mechanism
                                                                                                                                                                      • 3.4.4 Hydrolysis of Halogenoalkanes
                                                                                                                                                                        • 3.4.5 Reactivity of Halogenoalkanes
                                                                                                                                                                        • 3.5 Alcohols
                                                                                                                                                                          • 3.5.1 Classifying Alcohols
                                                                                                                                                                            • 3.5.2 Reactions of Alcohols
                                                                                                                                                                              • 3.5.3 Organic Liquid Preparation & Purification
                                                                                                                                                                              • 3.6 Modern Analytical Techniques I
                                                                                                                                                                                • 3.6.1 Mass Spectrometry
                                                                                                                                                                                  • 3.6.2 Infrared (IR) Spectroscopy
                                                                                                                                                                                • 4. Core Chemistry Practicals
                                                                                                                                                                                  • 4.1 Physical Chemistry Core Practicals
                                                                                                                                                                                    • 4.1.1 Molar Volume of a Gas
                                                                                                                                                                                      • 4.1.2 Standard Solutions
                                                                                                                                                                                        • 4.1.3 Determining Concentrations
                                                                                                                                                                                          • 4.1.4 Determining Enthalpy Change of Reaction
                                                                                                                                                                                          • 4.2 Inorganic & Organic Chemistry Core Practicals
                                                                                                                                                                                            • 4.2.1 Hydrolysis of Halogenoalkanes
                                                                                                                                                                                              • 4.2.2 Ethanol Oxidation
                                                                                                                                                                                                • 4.2.3 Chlorination of 2-Methylpropan-2-ol
                                                                                                                                                                                                  • 4.2.4 Qualitative Analysis
                                                                                                                                                                                                • 5. Advanced Physical Chemistry (A Level Only)
                                                                                                                                                                                                  • 5.1 Equilibrium II
                                                                                                                                                                                                    • 5.1.1 Deducing Kp Expressions
                                                                                                                                                                                                      • 5.1.2 Equilbrium Constant Calculations
                                                                                                                                                                                                        • 5.1.3 Reaction Conditions & The Equilibrium Constant
                                                                                                                                                                                                        • 5.2 Acid-base Equilibria
                                                                                                                                                                                                          • 5.2.1 Brønsted–Lowry Acids & Bases
                                                                                                                                                                                                            • 5.2.2 pH
                                                                                                                                                                                                              • 5.2.3 Acid Strength
                                                                                                                                                                                                                • 5.2.4 Ionic Product of Water
                                                                                                                                                                                                                  • 5.2.5 Measuring and Comparing pH
                                                                                                                                                                                                                    • 5.2.6 Titration Curves
                                                                                                                                                                                                                      • 5.2.7 Buffers
                                                                                                                                                                                                                        • 5.2.8 Weak Acid - Strong Base Titration
                                                                                                                                                                                                                        • 5.3 Energetics II: Born-Haber
                                                                                                                                                                                                                          • 5.3.1 Lattice Energy
                                                                                                                                                                                                                            • 5.3.2 Born-Haber Cycles
                                                                                                                                                                                                                              • 5.3.3 Polarising Power
                                                                                                                                                                                                                                • 5.3.4 Enthalpy of Solution
                                                                                                                                                                                                                                • 5.4 Energetics II: Entropy
                                                                                                                                                                                                                                  • 5.4.1 Introducing Entropy
                                                                                                                                                                                                                                    • 5.4.2 Entropy Calculations
                                                                                                                                                                                                                                      • 5.4.3 Gibbs Free Energy
                                                                                                                                                                                                                                        • 5.4.4 Feasible Reactions
                                                                                                                                                                                                                                        • 5.5 Kinetics II
                                                                                                                                                                                                                                          • 5.5.1 Rates of Reaction
                                                                                                                                                                                                                                            • 5.5.2 Rate Equations
                                                                                                                                                                                                                                              • 5.5.3 Rates - Experimental Techniques
                                                                                                                                                                                                                                                • 5.5.4 Initial Rates Method
                                                                                                                                                                                                                                                  • 5.5.5 Continuous Monitoring Method
                                                                                                                                                                                                                                                    • 5.5.6 Reaction Order Graphs
                                                                                                                                                                                                                                                      • 5.5.7 Rate-Determining Steps
                                                                                                                                                                                                                                                        • 5.5.8 Rates & Reaction Mechanisms
                                                                                                                                                                                                                                                          • 5.5.9 Arrhenius & Activation Energy
                                                                                                                                                                                                                                                        • 6. Advanced Inorganic Chemistry (A Level Only)
                                                                                                                                                                                                                                                          • 6.1 Redox II
                                                                                                                                                                                                                                                            • 6.1.1 Reduction & Oxidation
                                                                                                                                                                                                                                                              • 6.1.2 Standard Electrode Potential
                                                                                                                                                                                                                                                                • 6.1.3 Measuring Standard Electrode Potential
                                                                                                                                                                                                                                                                  • 6.1.4 Conventional Cell Representation
                                                                                                                                                                                                                                                                    • 6.1.5 Thermodynamics & Electrode Potential
                                                                                                                                                                                                                                                                      • 6.1.6 Disproportionation & Electrode Potential
                                                                                                                                                                                                                                                                        • 6.1.7 Storage Cells
                                                                                                                                                                                                                                                                          • 6.1.8 Fuel Cells
                                                                                                                                                                                                                                                                            • 6.1.9 Redox Titration Calculations
                                                                                                                                                                                                                                                                            • 6.2 Principles of Transition Metal Chemistry
                                                                                                                                                                                                                                                                              • 6.2.1 Transition Metals
                                                                                                                                                                                                                                                                                • 6.2.2 Transition Metal Complexes
                                                                                                                                                                                                                                                                                  • 6.2.3 Coloured Ions
                                                                                                                                                                                                                                                                                    • 6.2.4 Ligands
                                                                                                                                                                                                                                                                                      • 6.2.5 Octahedral Complexes
                                                                                                                                                                                                                                                                                        • 6.2.6 Tetrahedral Complexes
                                                                                                                                                                                                                                                                                          • 6.2.7 Cis-platin
                                                                                                                                                                                                                                                                                            • 6.2.8 Haemoglobin
                                                                                                                                                                                                                                                                                              • 6.2.9 Catalysis
                                                                                                                                                                                                                                                                                                • 6.2.10 Heterogeneous Catalysis
                                                                                                                                                                                                                                                                                                  • 6.2.11 Homogeneous Catalysis
                                                                                                                                                                                                                                                                                                    • 6.2.12 Autocatalysis
                                                                                                                                                                                                                                                                                                    • 6.3 Reactions of Transition Metal Elements
                                                                                                                                                                                                                                                                                                      • 6.3.1 Vanadium
                                                                                                                                                                                                                                                                                                        • 6.3.2 Chromium
                                                                                                                                                                                                                                                                                                          • 6.3.3 Reactions of Ions in Aqueous Solution
                                                                                                                                                                                                                                                                                                            • 6.3.4 Ligand Exchange
                                                                                                                                                                                                                                                                                                          • 7. Advanced Organic Chemistry (A Level Only)
                                                                                                                                                                                                                                                                                                            • 7.1 Organic Chemistry II: Chirality
                                                                                                                                                                                                                                                                                                              • 7.1.1 Chirality
                                                                                                                                                                                                                                                                                                              • 7.2 Organic Chemistry II: Carbonyl Chemistry
                                                                                                                                                                                                                                                                                                                • 7.2.1 Carbonyl Compounds
                                                                                                                                                                                                                                                                                                                  • 7.2.2 Testing for Carbonyls
                                                                                                                                                                                                                                                                                                                  • 7.3 Organic Chemistry II: Carboxylic Acids
                                                                                                                                                                                                                                                                                                                    • 7.3.1 Physical Properties of Carboxylic Acids
                                                                                                                                                                                                                                                                                                                      • 7.3.2 Preparation of Carboxylic Acids
                                                                                                                                                                                                                                                                                                                        • 7.3.3 Reactions of Carboxylic Acids
                                                                                                                                                                                                                                                                                                                          • 7.3.4 Acyl Chlorides & Esters
                                                                                                                                                                                                                                                                                                                          • 7.4 Organic Chemistry III: Aromatic Chemistry
                                                                                                                                                                                                                                                                                                                            • 7.4.1 Benzene Structure
                                                                                                                                                                                                                                                                                                                              • 7.4.2 Reactions of Benzene
                                                                                                                                                                                                                                                                                                                                • 7.4.3 Electrophilic Substitution
                                                                                                                                                                                                                                                                                                                                  • 7.4.4 Phenol
                                                                                                                                                                                                                                                                                                                                  • 7.5 Organic Chemistry III: Nitrogen Chemistry
                                                                                                                                                                                                                                                                                                                                    • 7.5.1 Amines, Amides, Amino Acids & Proteins
                                                                                                                                                                                                                                                                                                                                      • 7.5.2 Primary Aliphatic Amines
                                                                                                                                                                                                                                                                                                                                        • 7.5.3 Amine Basicity
                                                                                                                                                                                                                                                                                                                                          • 7.5.4 Aromatic Amine Formation
                                                                                                                                                                                                                                                                                                                                            • 7.5.5 Amide Chemistry
                                                                                                                                                                                                                                                                                                                                              • 7.5.6 Condensation Polymerisation
                                                                                                                                                                                                                                                                                                                                                • 7.5.7 Amino Acids & Proteins
                                                                                                                                                                                                                                                                                                                                                • 7.6 Organic Chemistry III: Organic Synthesis
                                                                                                                                                                                                                                                                                                                                                  • 7.6.1 Deducing Organic Structures
                                                                                                                                                                                                                                                                                                                                                    • 7.6.2 Planning Reaction Schemes
                                                                                                                                                                                                                                                                                                                                                      • 7.6.3 Increasing Chain Length
                                                                                                                                                                                                                                                                                                                                                        • 7.6.4 Organic Techniques - Preparation
                                                                                                                                                                                                                                                                                                                                                          • 7.6.5 Organic Techniques - Purification
                                                                                                                                                                                                                                                                                                                                                            • 7.6.6 Organic Techniques - Purity
                                                                                                                                                                                                                                                                                                                                                            • 7.7 Modern Analytical Techniques II
                                                                                                                                                                                                                                                                                                                                                              • 7.7.1 Mass Spectrometry
                                                                                                                                                                                                                                                                                                                                                                • 7.7.2 Carbon-13 NMR
                                                                                                                                                                                                                                                                                                                                                                  • 7.7.3 Proton NMR
                                                                                                                                                                                                                                                                                                                                                                    • 7.7.4 Thin-Layer Chromatography
                                                                                                                                                                                                                                                                                                                                                                      • 7.7.5 Other Chromatography
                                                                                                                                                                                                                                                                                                                                                                    • 8. Advanced Core Practicals (A Level Only)
                                                                                                                                                                                                                                                                                                                                                                      • 8.1 Advanced Physical Chemistry Core Practicals
                                                                                                                                                                                                                                                                                                                                                                        • 8.1.1 Finding Ka Values
                                                                                                                                                                                                                                                                                                                                                                          • 8.1.2 Electrochemical Cells
                                                                                                                                                                                                                                                                                                                                                                            • 8.1.3 Rates of Reaction
                                                                                                                                                                                                                                                                                                                                                                              • 8.1.4 Activation Energy
                                                                                                                                                                                                                                                                                                                                                                              • 8.2 Advanced Inorganic & Organic Chemistry Core Practicals
                                                                                                                                                                                                                                                                                                                                                                                • 8.2.1 Redox Titration
                                                                                                                                                                                                                                                                                                                                                                                  • 8.2.2 Transition Metal Complexes
                                                                                                                                                                                                                                                                                                                                                                                    • 8.2.3 A-Level Qualitative Analysis
                                                                                                                                                                                                                                                                                                                                                                                      • 8.2.4 Aspirin Preparation


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                                                                                                                                                                                                                                                                                                                                                                                    Author: Philippa

                                                                                                                                                                                                                                                                                                                                                                                    Philippa has worked as a GCSE and A level Chemistry teacher and tutor for over thirteen years. She studied Chemistry and Sport Science at Loughborough University graduating in 2007 having also completed her PGCE in science. Throughout her time as a teacher she was in charge of a boarding house for five years and coached many teams in a variety of sports. When not producing resources with the chemistry team, Philippa enjoys gardening with her two young daughters and going to CrossFit sessions at her local gym.


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