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Organic Chemistry I: 3.5 Lewis Acids and Lewis Bases

Organic Chemistry I
3.5 Lewis Acids and Lewis Bases
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table of contents
  1. Cover
  2. Title Page
  3. Copyright
  4. Table Of Contents
  5. Introduction
  6. Acknowledgements
  7. Chapter 1 Basic Concepts in Chemical Bonding and Organic Molecules
    1. 1.1 Chemical Bonding
    2. 1.2 Lewis Structure
    3. 1.3 Resonance Structures
    4. 1.4 Resonance structures in Organic Chemistry
    5. 1.5 Valence-Shell Electron-Pair Repulsion Theory (VSEPR)
    6. 1.6 Valence Bond Theory and Hybridization
    7. Answers to Practice Questions Chapter 1
  8. Chapter 2 Fundamental of Organic Structures
    1. 2.1 Structures of Alkenes
    2. 2.2 Nomenclature of Alkanes
    3. 2.3 Functional Groups
    4. 2.4 IUPAC Naming of Organic Compounds with Functional Groups
    5. 2.5 Degree of Unsaturation/Index of Hydrogen Deficiency
    6. 2.6 Intermolecular Force and Physical Properties of Organic Compounds
    7. Answers to Practice Questions Chapter 2
  9. Chapter 3 Acids and Bases: Organic Reaction Mechanism Introduction
    1. 3.1 Review of Acids and Bases and Ka
    2. 3.2 Organic Acids and Bases and Organic Reaction Mechanism
    3. 3.3 pKa of Organic Acids and Application of pKa to Predict Acid-Base Reaction Outcome
    4. 3.4 Structural Effects on Acidity and Basicity
    5. 3.5 Lewis Acids and Lewis Bases
    6. Answers to Practice Questions Chapter 3
  10. Chapter 4 Conformations of Alkanes and Cycloalkanes
    1. 4.1 Conformation Analysis of Alkanes
    2. 4.2 Cycloalkanes and Their Relative Stabilities
    3. 4.3 Conformation Analysis of Cyclohexane
    4. 4.4 Substituted Cyclohexanes
    5. Answers to Practice Questions Chapter 4
  11. Chapter 5 Stereochemistry
    1. 5.1 Summary of Isomers
    2. 5.2 Geometric Isomers and E/Z Naming System
    3. 5.3 Chirality and R/S Naming System
    4. 5.4 Optical Activity
    5. 5.5 Fisher Projection
    6. 5.6 Compounds with More Than One Chirality Centers
    7. Answers to Practice Questions Chapter 5
  12. Chapter 6 Structural Identification of Organic Compounds: IR and NMR Spectroscopy
    1. 6.1 Electromagnetic Radiation and Molecular Spectroscopy
    2. 6.2 Infrared (IR) Spectroscopy Theory
    3. 6.3 IR Spectrum and Characteristic Absorption Bands
    4. 6.4 IR Spectrum Interpretation Practice
    5. 6.5 NMR Theory and Experiment
    6. 6.6 ¹H NMR Spectra and Interpretation (Part I)
    7. 6.7 ¹H NMR Spectra and Interpretation (Part II)
    8. 6.8 ¹³C NMR Spectroscopy
    9. 6.9 Structure Determination Practice
    10. Answers to Practice Questions Chapter 6
  13. Chapter 7 Nucleophilic Substitution Reactions
    1. 7.1 Nucleophilic Substitution Reaction Overview
    2. 7.2 SN2 Reaction Mechanism, Energy Diagram and Stereochemistry
    3. 7.3 Other Factors that Affect SN2 Reactions
    4. 7.4 SN1 Reaction Mechanism, Energy Diagram and Stereochemistry
    5. 7.5 SN1 vs SN2
    6. 7.6 Extra Topics on Nucleophilic Substitution Reaction
    7. Answers to Practice Questions Chapter 7
  14. Chapter 8 Elimination Reactions
    1. 8.1 E2 Reaction
    2. 8.2 E1 Reaction
    3. 8.3 E1/E2 Summary
    4. 8.4 Comparison and Competition Between SN1, SN2, E1 and E2
    5. Answers to Practice Questions Chapter 8
  15. Chapter 9 Free Radical Substitution Reaction of Alkanes
    1. 9.1 Homolytic and Heterolytic Cleavage
    2. 9.2 Halogenation Reaction of Alkanes
    3. 9.3 Stability of Alkyl Radicals
    4. 9.4 Chlorination vs Bromination
    5. 9.5 Stereochemistry for Halogenation of Alkanes
    6. 9.6 Synthesis of Target Molecules: Introduction of Retrosynthetic Analysis
    7. Answers to Practice Questions Chapter 9
  16. Chapter 10 Alkenes and Alkynes
    1. 10.1 Synthesis of Alkenes
    2. 10.2 Reactions of Alkenes: Addition of Hydrogen Halide to Alkenes
    3. 10.3 Reactions of Alkenes: Addition of Water (or Alcohol) to Alkenes
    4. 10.4 Reactions of Alkenes: Addition of Bromine and Chlorine to Alkenes
    5. 10.5 Reaction of Alkenes: Hydrogenation
    6. 10.6 Two Other Hydration Reactions of Alkenes
    7. 10.7 Oxidation Reactions of Alkenes
    8. 10.8 Alkynes
    9. Answers to Practice Questions Chapter 10
  17. About the Author

3.5 Lewis Acids and Lewis Bases

The Brønsted-Lowry definition works well for the reactions we learned so far, however it also limits the scope of acid-base reactions in a way where the proton H+ must be involved. Lewis acids and Lewis bases are defined in a more inclusive way that was first introduced by G. N. Lewis in 1923.

Lewis Acid: a species that can accept an electron pair;

Lewis Base: a species that can donate an electron pair.

All Brønsted-Lowry acids and bases fit into the Lewis definition, because the proton transfer process is essentially the reaction where the base uses its electron pair to accept a proton, as indicated by the mechanism arrow that we learned earlier. Therefore in the following reaction, the BL acid, H+, is also the Lewis acid, and BL base, NH3, also fits to the definition of the Lewis base.

NH3 (BL Base donates electron pair) while the (H+) (BL acid accepts electron pair to create (NH4+)
Figure 3.5a Lewis base & Lewis acid reaction

However, the Lewis definition is broader and covers more situations. For the following reaction, B(CH3)3 is the Lewis acid because boron has an incomplete octet, and the empty 2p orbital on boron is able to accept electrons. (CH3)3N behaves as the Lewis base with the lone pair electron on N that is able to be donated.

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Figure 3.5b LA-LB adduct

The product between Lewis acids and Lewis bases is usually a species that has the acid and base joined together, and the product is called the “LA-LB adduct”.

Other examples of Lewis acids include electron-deficient species, such as H+, M+, M2+, BH3, BF3, AlCl3 etc. Lewis bases can be: amine, ether or other species that have lone pair electrons to donate.

Exercises 3.3

Show the product of the following LA-LB reaction:
BF3 + CH2CH3-O-CH2CH3 =
Answers to Practice Questions Chapter 3

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