Skip to main content

Organic Chemistry I: 3.1 Review of Acids and Bases and Ka

Organic Chemistry I
3.1 Review of Acids and Bases and Ka
    • Notifications
    • Privacy
  • Project HomeNatural Sciences Collection: Anatomy, Biology, and Chemistry
  • Projects
  • Learn more about Manifold

Notes

Show the following:

  • Annotations
  • Resources
Search within:

Adjust appearance:

  • font
    Font style
  • color scheme
  • Margins
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

3.1 Review of Acids and Bases and Ka

The most commonly applied definition of acids and bases is the Brønsted-Lowry definition:

  • Brønsted-Lowry Acid: a substance that can donate a proton (H+);
  • Brønsted-Lowry Base: a substance that can accept a proton (H+).

Therefore, according to the Brønsted-Lowry definition, an acid-base reaction is a proton transfer process in which the acid gives away a proton and base accepts a proton as shown in the general equation:

HA (acid) + B (base) = A- (conjugate base) + HB+ (conjugate acid)

General equation for acid-base reaction

The species that forms when an acid loses its proton is called the conjugate base of that acid; similarly, the species that forms when a base accepts a proton is called the conjugate acid of that base. In the general equation above, HA is the conjugate acid of A–, and A– is the conjugate base of HA. HA and A– can also be called a conjugate acid-base pair; another pair is HB+ and B.

A strong acid donates the proton completely, and the arrow “→” can be used in the reaction equation to indicate that the reaction goes to completion. The dissociation reaction of the strong acid HCl in water is used as an example here:

HCl (g) + H2O (l) →H3O+(aq) + Cl–(aq)

For weak acids (HA is used as a general formula), the proton is only donated partially and the reaction stays at equilibrium. The equilibrium arrow “""” will be needed in the reaction equation to indicate the equilibrium status:

HA (aq) + H2O (l) ⇔ H3O+ (aq) + A– (aq)

The equilibrium constant for the above reaction is called the acid dissociation constant, Ka. It is a constant to measure the relative strength of an acid. The expression for Ka is:

Ka = [H3O+][A-]/[HA]

The larger the Ka value, the stronger the ability of the acid to donate protons, and the stronger the acid is. (Technically, when the Ka value is larger than 10, the acid can be regarded as a strong acid.)

For the conjugate acid-base pair, the stronger the acid, the weaker the conjugate base is, and vice versa.

Annotate

Next Chapter
3.2 Organic Acids and Bases and Organic Reaction Mechanism
PreviousNext
Chemistry
The LibreTexts libraries are Powered by NICE CXone Expert and are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Legal. Accessibility Statement For more information contact us at info@libretexts.org.
Powered by Manifold Scholarship. Learn more at
Opens in new tab or windowmanifoldapp.org