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DP IB Chemistry: HL

Revision Notes

Home / IB / Chemistry: HL / DP / Revision Notes / 20. HL Organic Chemistry / 20.3 Stereoisomerism / 20.3.1 Stereoisomers


20.3.1 Stereoisomers


Conformational & Configurational Isomers

  • Isomers are compounds that have the same molecular formula but a different arrangement of atoms
  • Isomers can be grouped into various categories, as shown:
20-3-1-flow-chart-of-the-various-isomers-with-points-to-help-identify-them

 

Flow chart of the various isomers with points to help identify them

  • At Standard Level, we encountered three types of structural isomers:
    • Functional group isomers, e.g. propanal and propanone
    • Position isomers, e.g. propan-1-ol and propan-2-ol
    • Branch-chain isomers, e.g. butane and methylpropane

  • If the atoms within an isomer are arranged in the same order then we are dealing with stereoisomers
    • Stereoisomers can be conformational or configurational

Conformational Isomers

  • Conformational isomers, or conformers, occur due to free rotation about a single σ-bond and can be described as:
    • Staggered
    • Eclipsed

  • One of the simplest examples of conformational isomerism is ethane, CH3CH3

Three-dimensional structure of ethane identifying the bond for conformational isomerism, downloadable IB Chemistry revision notes

Three-dimensional structure of ethane identifying the bond for conformational isomerism

  • By looking along the C-C bond highlighted in the diagram we can draw the two Newman projections, staggered and eclipsed

The staggered and eclipsed conformers of ethane, downloadable IB Chemistry revision notes

The staggered and eclipsed conformers of ethane

  • The staggered conformer has angles between hydrogen atoms on adjacent carbons of 60o, as shown
    • It is also more stable / lower energy than the eclipsed conformer because the C-H bonds are as far apart as possible to minimise the repulsion between the electrons in the C-H bonds

  • The eclipsed conformer has angles between hydrogen atoms on adjacent carbons of 0o, this is not shown in the diagrams so that the conformation can be seen
    • The eclipsed conformer is less stable / higher energy due to the repulsion between the electrons in the C-H bonds that are closer together

  • The free rotation that causes these conformers means that it is easy to interconvert from one conformer to the other and back
    • This is also the reason that it is almost impossible to isolate a single conformer

Conformational Isomerism in Cyclic Structures

  • Conformational isomerism can also be seen in cyclic structures
  • A common example of this is cyclohexane, C6H12
    • Cyclohexane isomers exist in boat and chair forms:

Skeletal structures showing the boat and chair forms of cyclohexane, downloadable IB Chemistry revision notes

Skeletal structures showing the boat and chair forms of cyclohexane

  • The boat form is less stable / higher energy as there are four eclipsed bonds causing strain on the overall structure
    • There is also repulsion of the hydrogen atoms on the end of the boat structure

  • It is possible to "flip" between the boat and chair forms which explains the difficulty in isolating just one of the forms
    • During the interconversions, it also possible to get other structures commonly called the half chair and the twisted boat

Configurational Isomers

  • Interconversion of configurational isomers can only occur by breaking bonds or rearranging stereocentres
  • Configurational isomers can be divided into:
    • cis / trans isomers and E / Z isomers
    • optical isomers



  • 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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