Based on the premise that many, if not most, reactions in organic chemistry can be explained by variations of fundamental acid-base concepts, Organic Chemistry: An Acid-Base Approach provides a framework for understanding the subject that goes beyond mere memorization. Using several techniques to develop a relational understanding, it helps students fully grasp the essential concepts at the root of organic chemistry.

This new edition was rewritten largely with the feedback of students in mind and is also based on the author's classroom experiences using the previous editions.

Highlights of the Third Edition Include:

• Extensively revised chapters that improve the presentation of material.
  
  
• Features the contributions of more than 65 scientists, highlighting the diversity in organic chemistry.
  
  
• Features the current work of over 30 organic chemists, highlighting the diversity in organic chemistry.

• Many new reactions are featured that are important in modern organic chemistry.

• Video lectures are provided in a .mov format, accessible online as a 'built-in' ancillary for the book.

• Instructor and Student Resources -includes scientist images and solutions manual for instructors.

The third edition of Organic Chemistry: An Acid-Base Approach constitutes a significant improvement upon a unique introductory technique to organic chemistry. The reactions and mechanisms it covers are the most fundamental concepts in organic chemistry that are applied to industry, biological chemistry, biochemistry, molecular biology, and pharmacy. Using an illustrated conceptual approach rather than presenting sets of principles and theories to memorize, it gives students a more concrete understanding of the material.

Professor Michael B. Smith was born in Detroit, Michigan in 1946 and moved to Madison Heights, Virginia in 1957, where he attended high school at Amherst County High School. He received an A.A. from Ferrum College in 1967 and a B.S. in chemistry from Virginia Polytechnic Institute in 1969. After working for three years at the Newport News Shipbuilding and Dry Dock Co. in Newport News VA as an analytical chemist, he entered graduate school at Purdue University. He received a Ph.D. in Organic chemistry in 1977, under the auspices of Professor Joe Wolinsky. Professor Smith spent one year as a faculty research associate at the Arizona State University with Professor G. Robert Pettit, working on the isolation of cytotoxic principles from plants and sponges. He spent a second year of postdoctoral work with Professor Sidney M. Hecht at the Massachusetts Institute of Technology, working on the synthesis of bleomycin A2. Professor Smith began his academic career at the University of Connecticut in 1979, where he achieved the rank of professor of chemistry. In 1986 he spent a sabbatical leave in the laboratories of Professor Leon Ghosez, at the Université Catholique de Louvain in Louvain-la-Neuve, Belgium, as a visiting professor. He retired as a full professor from the University of Connecticut on January 1, 2017, and is currently pursuing his interests as an author.

Chapter 1: Introduction

1.1. A Brief History of Organic Chemistry

1.2. The Variety and Beauty of Organic Molecules

Chapter 2: Why Is an Acid-Base Theme Important?

2.1. Traditional Acid and Base Theory

2.2. There are Two Acid-Base Definitions: How Are They Related?

2.3. Acid-Base Equilibria and Equilibrium Constants

2.4. Electronegativity and Atom Size

2.4.A. Electronegativity

2.4. B. Atom Size

2.5. Atom Size and Electronegativity Arguments Applied to Acids and Bases

2.6. Resonance, Electron Dispersion and Base Strength

2.7. Lewis Acids and Bases

2.8. Why Is Acid-Base Chemistry a Theme for Organic Chemistry?

2.9. Biological Relevance

Correlation of Homework with Concepts

ANSWERS TO IN-CHAPTER QUESTIONS

HOMEWORK

Chapter 3: Bonding

3.1. Atomic orbitals and Electrons

3.1.A. Atomic Orbitals

3.1.B. Electronic Configuration

3.2. Ionic versus Covalent Chemical Bonds

3.3. Covalent Bonds

3.4. Linear Combination of Atomic Orbital (LCAO) Model

3.5. Tetrahedral Carbons and sp3 Hybridization

3.5.A. The Experimentally Determined Structure of Methane

3.5.B. Electron Promotion and sp3 Hybridization

3.5.C. The Hybrid Carbon Model of sp3-Hybrid Orbitals

3.6. The Valence Shell Electron Pair Repulsion (VSEPR) Model

3.7. Breaking Covalent Bonds

3.8. Carbon Bonded to Heteroatoms

3.8.A. A Covalent Bond Between Carbon and a Heteroatom: Bond Polarization

3.8.B. Bond Polarity, Bond Moments, and Bond Strength

Correlation of Homework with Concepts

ANSWERS TO IN-CHAPTER QUESTIONS

HOMEWORK

Chapter 4: Alkanes, Isomers, and an Introduction to Nomenclature

4.1. Alkanes

4.2. Structural Variations of Alkane Hydrocarbons

4.2.A. Straight-chain and Branched Alkanes

4.2.B. Isomers

4.3. The IUPAC Rules of Nomenclature

4.3.A. Prefixes and Simple Alkanes

4.3.B. Common Names

4.3.C. Halogens are Substituents

4.3.D. Multiple Substituents

4.3.E. Complex Substituents

4.4. Rings Made of Carbon: Cyclic Compounds

4.5. The Acid or Base Properties of Alkanes

4.6. Combustion Analysis and Empirical Formulas

4.7. Commercial and Biological Relevance

Correlation of Homework with Concepts

ANSWERS TO IN-CHAPTER QUESTIONS

HOMEWORK

Chapter 5: Functional Groups

5.1. -Bonds. The C=C Unit and Alkenes

5.2. -Bonds. The CºC Unit and Alkynes

5.3. Hydrocarbons With Several -Bonds

5.4. Terpenes

5.5. Heteroatom Functional Groups

5.5.A. Alcohols and Thiols

5.5.B. Ethers and Dithioethers (Sulfides)

5.5.C. Amines

5.6. Functional Groups With Polarized -Bonds

5.6.A. The Carbonyl Functional Group, C=O

5.6.B. Ketones and Aldehydes

5.6.C. Carboxylic Acids, Carboxylic Anions and Resonance

5.6.D. Double and Triple Bonds to Nitrogen

5.7. Acid-Base Properties of Functional Groups

5.8. Physical Properties and Intermolecular Forces

5.8.A. Boiling Point

5.8.B. Solubility

5.8.C. Melting Point

5.9. Benzene: A Special Cyclic Hydrocarbon

5.10. Biological Relevance

Correlation of Homework with Concepts

ANSWERS TO IN-CHAPTER QUESTIONS

HOMEWORK

Chapter 6: Acids, Bases, and Nucleophiles

6.1. Acid-Base Equilibria

6.2. Carboxylic Acids and Sulfonic Acids

6.2.A. Carboxylic Acids

6.2.B Sulfonic Acids

6.3. Factors That Influence the Strength of a Carboxylic Acid

6.3.A. Stability of the Conjugate Base

6.3.B. Inductive Effects

6.3.C. Solvent Effects

6.4. Alcohols Are Amphoteric

6.5. Amines

6.6. Carbon Acids

6.6.A. Terminal Alkynes Are Weak Acids

6.6.B. -Hydrogen Atoms and Carbonyls

6.7. Organic Bases

6.7.A. Amines

6.7.B. Alcohols Are Bases

6.7.C. Ethers Are Bases

6.7.D. Carbonyl Compounds Are Bases

6.7.E. Alkenes and Alkynes Are Bases

6.8. Lewis Acids and Bases

6.9. Nucleophiles

6.10. Biological Relevance

Correlation of Homework with Concepts

ANSWERS TO IN-CHAPTER QUESTIONS

HOMEWORK

Chapter 7. Chemical Reactions, Bond Energy, and Kinetics

7.1. A Chemical Reaction

7.2. Reactive In…