Organic Chemistry: An Acid-Base Approach, Second Edition, 2nd Edition (Paperback) book cover

Organic Chemistry

An Acid-Base Approach, Second Edition, 2nd Edition

By Michael B. Smith

CRC Press

1,128 pages | 2777 Color Illus.

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pub: 2018-06-14
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Description

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 first edition.

Highlights of the Second Edition Include:

  • Reorganized chapters that improve the presentation of material
  • Coverage of new topics, such as green chemistry
  • Adding photographs to the lectures to illustrate and emphasize important concepts
  • A downloadable solutions manual

The second 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.

Reviews

Praise for the first edition:

"Summing Up: Recommended"

—CHOICE, June 2011

"After a brief historical overview and a chapter on the acid-base theme, the standard programme is rolled out, although with an almost unbroken emphasis on the acid-base approach…

… the body of the text is easy to read, and the well chosen questions following almost every paragraph encourage the reader to start digesting the provided information immediately."

—Martina Lahmann in Education in Chemistry, May 2011

"This new book is designed to provide a new approach to teaching organic chemistry, to understand the relationships between functional group via an acid-base theme. In 28 chapters the author provides a mechanistic approach to teaching organic chemistry, focusing on fundamental principles rather than a comprehensive accumulation of factual knowledge."

Organic Process Research, 2011

Table of Contents

Introduction

Brief History of Organic Chemistry

Variety and Beauty of Organic Molecules

Notes

Why Is an Acid–Base Theme Important?

Acids and Bases in General Chemistry

Acids and Bases in Organic Chemistry

There Are Two Acid–Base Definitions: How Are They Related?

Acid and Base Strength

Electronegativity and Atom Size

Determination of Acid–Base Strength Based on Electronegativity and Size Arguments

Lewis Acids and Bases

Why Is Acid–Base Chemistry a Theme for Organic Chemistry?

Biological Relevance

Correlation of Concepts with Homework

Answers to In-Chapter Questions

Homework

Notes

Bonding

Orbitals and the Periodic Table

Ionic versus Covalent Chemical Bonds

Covalent Bonds

Strength of a Covalent Bond

Molecular Orbitals

Tetrahedral Carbons and sp3 Hybridization

Breaking Covalent Bonds

Polarized Covalent σ-Bonds

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Alkanes, Isomers, and an Introduction to Nomenclature

Fundamental Structure of Alkanes Based on the sp3-Hybrid Model

Millions of Alkane Hydrocarbons

Acid or Base Properties of Alkanes

Naming Millions of Isomers: Rules of Nomenclature: The IUPAC Rules of Nomenclature

Rings Made of Carbon: Cyclic Compounds

Combustion Analysis and Empirical Formulas

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Functional Groups

Introducing a Functional Group: Alkenes

Acid–Base Properties of Alkenes

Hydrocarbon Functional Groups: Alkynes

Hydrocarbons with Several π-Bonds

Heteroatoms and Polarized Covalent σ-Bonds

Formal Charge

Reactive Intermediates

Heteroatom Functional Groups

Acid–Base Properties of Functional Groups

Physical Properties and Intermolecular Forces

Functional Groups with Polarized π-Bonds

Benzene: A Special Cyclic Hydrocarbon

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Acids, Bases, Nucleophiles, and Electrophiles

Acid–Base Equilibria

Factors That Influence Ka

Factors That Influence the Strength of a Carboxylic Acid

Energetics and Reaction Curves

Alcohols and Amines Are Acids

Hydrogen Atom Attached to a Carbon Is an Acid

Acid–Base Reaction of Alkenes with Mineral Acids

Lewis Acids and Bases

Organic Bases

Nucleophiles

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Chemical Reactions, Bond Energy, and Kinetics

Chemical Reaction

Free Energy: Influence of Enthalpy and Entropy

Bond-Dissociation Enthalpy and Reactions

Transition States

Energetics: Starting Materials, Transition States, Intermediaries, and Products on a Reaction Curve

Competing Reactions

Reaction Curves and Intermediaries

Mechanisms

Why Does a Chemical Reaction Occur? Defining a "Reactive" Center

Reversible Chemical Reactions

Kinetics

No Reaction

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Rotamers and Conformation

Rotamers

Longer Chain Alkanes

Conformations of Alkenes and Alkynes: Introducing π-Bonds

Influence of Heteroatoms on the Rotamer Population

Cyclic Alkanes

Substituted Cyclohexanes

Larger Rings

Cyclic Alkenes

Introducing Heteroatoms into a Ring

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Stereoisomers: Chirality, Enantiomers, and Diastereomers

Stereogenic Carbons and Stereoisomers

Absolute Configuration [(R) and (S) Nomenclature]

Specific Rotation: A Physical Property

Relationship of Specific Rotation and Absolute Configuration

Mixtures of Enantiomers and Racemates

Alkenes

Diastereomers

Stereogenic Centers in Cyclic Molecules

Stereogenic Centers in Complex Molecules

Optical Resolution

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Acid–Base Reactions of π-Bonds: Addition Reactions

Alkenes and Acid–Base Chemistry

Carbocation Intermediates

Alkenes React with Weak Acids in the Presence of an Acid Catalyst

Alkenes React as Lewis Bases with Dihalogens

Alkenes React as Lewis Bases with Borane

Alkenes React as Lewis Bases with Mercury(II) Compounds

Alkynes React as Brønsted–Lowry Bases or Lewis Bases

Oxidation Reactions of Alkenes

Nonionic Reactions: Radicals and Alkene Polymerization

Synthetic Transformations

Organization of Reaction Types

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Nucleophiles: Lewis Base-Like Reactions at sp3 Carbon

Alkyl Halides, Sulfonate Esters, and the Electrophilic C-X Bond

Nucleophiles and Bimolecular Substitution (the SN2 Reaction)

Functional Group Transformations via the SN2 Reaction

Tertiary Halide Reacts with a Nucleophile When the Solvent Is Water

Solvolysis Reactions of Alkyl Halides

Preparation of Halides by Substitution Reactions

Reactions of Ethers

Free Radical Halogenation of Alkanes

Synthetic Transformations

Organization of Reaction Types

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Bases-Induced Elimination Reactions

Bimolecular Elimination

Stereochemical Consequences of the E2 Reaction

E2 Reaction in Cyclic Molecules

Unimolecular Elimination: The E1 Reaction

Intramolecular Elimination

1,3-Elimination: Decarboxylation

Elimination Reactions of Vinyl Halides: Formation of Alkynes

Functional Group Exchanges Based on Elimination

Organization of Reaction Types

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Substitution and Elimination Reactions Can Compete

Few Simplifying Assumptions

Protic versus Aprotic and Water

Nucleophilic Strength versus Base Strength

Nature of the Halide

What about Secondary Halides?

Strength and Limitations of the Simplifying Assumptions

When Do the Assumptions Fail?

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Spectroscopic Methods of Identification

Light and Energy

Mass Spectrometry

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Identifying Monofunctional Molecules

Carbon-13 NMR Spectroscopy: Counting the Carbons

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Organic Molecules That Contain Alkali Metals or Transition Metals (Organometallics)

Introducing Magnesium into a Molecule

Reaction of Aryl and Vinyl Halides with Magnesium

Grignard Reagents Are Bases

Grignard Reagents Are Poor Nucleophiles with Alkyl Halides

Organolithium Reagents

Organocuprates

Organometallic Disconnections

Organization of Reaction Types

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Carbonyl Compounds: Structure, Nomenclature, Reactivity

Carbonyl Group

Aldehydes and Ketones: Nomenclature

Chemical Reactivity of Ketones and Aldehydes

Carboxylic Acids: Nomenclature and Properties

Dicarboxylic Acids

Dicarboxylic Acids Have Two pKa Values

Carboxylic Acid Derivatives: Structure and Nomenclature

Acyl Substitution with Carboxylic Acid Derivatives

Sulfonic Acids

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Oxidation

Defining and Oxidation

Oxidation of Alcohols with Chromium (VI)

Oxidation of Alkenes Revisited

Oxidative Cleavage

Summary of Functional Group Exchanges

Organization of Reaction Types

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Reactions of Aldehydes and Ketones

Chemical Reactivity of the Carbonyl Group

Reaction of Aldehydes or Ketones with Strong Nucleophiles

Weak Nucleophiles: Reversible versus Irreversible Acyl Addition

Alcohols: Weak Nucleophiles That Yield Reactive Products

Amines Are Nucleophiles

Carbon–Carbon Bond-Forming Reactions and Functional Group Modification

Organization of Reaction Types

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Reduction

Defining a Reduction

Hydrides as Reducing Agents

Hydride Reduction of Other Functional Groups

Catalytic Hydrogenation

Dissolving Metal Reductions

Summary of Functional Group Exchanges

Organization of Reaction Types

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Carboxylic Acid Derivatives and Acyl Substitution

Chemical Reactivity of Carboxylic Acid Derivatives

Acyl Substitution: Hydrolysis of Acid Derivatives

Preparation of Acid Chlorides

Preparation of Acid Anhydrides

Preparation of Esters

Preparation of Amides

Reaction of Carboxylic Acid Derivatives with Carbon Nucleophiles

Reaction of Organometallics with Electrophilic "Carbonyl" Molecules

Dicarboxylic Acid Derivatives

Baeyer–Villiger Oxidation

Sulfonic Acids and Derivatives

Nitrate Esters, Sulfate Esters, and Phosphate Esters

Nitriles Are Carboxylic Acid Derivatives

Carbon–Carbon Bond-Forming Reactions and Functional Group Exchanges of Acid Derivatives

Organization of Reaction Types

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Aromatic Compounds and Benzene Derivatives

Benzene and Aromaticity

Functionalized Benzene Derivatives and a New Nomenclature System

Electrophilic Aromatic Substitution

Disubstituted Benzene Derivatives

Polysubstituted Benzene Derivatives

Reduction of Aromatic Compounds

Aromaticity in Monocyclic Molecules Other than Benzene

Polynuclear Aromatic Hydrocarbons

Nucleophilic Aromatic Substitution

Aromatic Amines and Diazonium Salts

Benzyne Intermediates

Aromatic Disconnections and Functional Group Exchange Reactions

Synthesis of Aromatic Compounds

Organization of Reaction Types

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Enolate Anions: Acyl Addition and Acyl Substitution

Aldehydes and Ketones Are Weak Acids

Nonnucleophilic Bases

Enolate Alkylation

Acyl Addition Reactions

Enolate Anions from Unsymmetrical Ketones

Intramolecular Aldol Condensation

Ester Enolate Anions

Decarboxylation

Knoevenagel Reaction, the Malonic Ester Synthesis, and the Acetoacetic Acid Synthesis

Phosphorus Ylids and the Wittig Reaction

New Synthetic Possibilities

Organization of Reaction Types

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Difunctional Molecules: Dienes and Conjugated Carbonyl Compounds

Conjugated Dienes

Conjugated Carbonyl Compounds

Detecting Conjugation with Spectroscopy

Reactions of Conjugated π-Bonds

Michael Addition

Hydroperoxide Anions and Conjugated Carbonyls

Synthetic Possibilities

Organization of Reaction Types

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Difunctional Molecules: Pericyclic Reactions

The Diels–Alder Reaction

Reactivity of Dienes and Alkenes

Selectivity in the Diels–Alder Reaction

Sigmatropic Rearrangements

Review of Synthetic Transformations

Organization of Reaction Types

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Retrosynthesis and Synthesis

What Is Synthesis?

Synthesis Based on a Specified Starting Material for a Given Target

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Heteroaromatic Compounds

Nitrogen in an Aromatic Ring

Oxygen and Sulfur in an Aromatic Ring

Substitution Reactions in Monocyclic Heterocyclic Aromatic Compounds

Reduced Forms of Heterocycles

Heteroaromatic Compounds with More Than One Ring

Aromatic Substitution Reactions of Polycyclic Heterocycles

Biological Relevance

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Multifunctional Compounds: Amino Acids and Peptides

Review of Reactions That Form Amines

Reactions of Amines

Difunctional Molecules: Amino Acids

Synthesis of α-Amino Acids

Biological Relevance: Peptides Are Poly(amides) of Amino Acid Residues

Biological Relevance: Proteins and Enzymes Are Poly(peptides)

Determination of the Primary Structure of a Peptide

New Synthetic Methodology

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

Multifunctional Compounds: Carbohydrates

Polyhydroxy Carbonyl Compounds

Disaccharides, Trisaccharides, Oligosaccharides, and Polysaccharides

Reactions of Carbohydrates

Biological Relevance: Nucleosides and Nucleotides

Biological Relevance: Polynucleotides

Correlation of Homework with Concepts

Answers to In-Chapter Questions

Homework

Notes

About the Author

Michael B. Smith, University of Connecticut, Storrs, USA

Subject Categories

BISAC Subject Codes/Headings:
MED008000
MEDICAL / Biochemistry
SCI013040
SCIENCE / Chemistry / Organic
SCI013050
SCIENCE / Chemistry / Physical & Theoretical