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DP IB Chemistry: HL

Revision Notes

Home / IB / Chemistry: HL / DP / Revision Notes / 4. Chemical Bonding & Structure / 4.2 Resonance, Shapes & Giant Structures / 4.2.1 Resonance Structures


4.2.1 Resonance Structures


Resonance Structures

  • The delocalization of electrons can explain the structures of some species that don’t seem to fit with a Lewis structure
  • Delocalized electrons are electrons in a molecule, ion or solid metal that are not associated with a single atom or one covalent bond
  • The Lewis diagram for the nitrate (V) ion gives a molecule with a double and two single bonds
  • There are three possible Lewis Structures
  • These structures are called resonance structures
  • However, studies of the electron density and bond length in the nitrate (V) ion indicate all the bonds are equal in length and the electron density is spread evenly between the three oxygen atoms
    • The bond length is intermediate between a single and a double bond
    • The actual structure is something in between the resonance structures and is known as a resonance hybrid

Resonance structures of the nitrate (V) ion

  • To determine the Lewis structure of the nitrate (V) ion first count the number of valence electrons and then add one electron for the negative charge on the ion

Number of valence electrons  = N + 3O +1

            = 5 + ( 3 x 6) + 1 = 24 electrons

  • Three structures are possible, consisting of a double bond and two singles:

Resonance structures in the nitrate ion

  • Dotted lines are used to show the position of the delocalised electrons

Resonance hybrid nitrate (V) ion

  • The criteria for forming resonance hybrids structures is that molecules must have a double bond (pi bond) that is capable of migrating from one part of a molecule to another
  • This usually arises when there are adjacent atoms with equal electronegativity and lone pairs of electrons that can re-arrange themselves and allow the double bonds to be in different positions
  • Other examples that you should know about are the carbonate ion, benzene, ozone and the carboxylate anion

Resonance Hybrids Table

  • Below are some other resonance structures and hybrids that you should know:


  • 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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