Skip Navigation

Book Search

< Back to Search Results

Organic Chemistry

An Acid-Base Approach, Second Edition

Edition:
2nd
Author(s):
Michael B. Smith
ISBN:
9781482238235
Format:
Hardback
Publication Date:
December 08, 2015
Content Details:
1,128 pages | 2,777 illustrations
Language:
English

Your Cart:

List Price:   $155.00

  
add to cart

Also of Interest

  • About the Book

    Book Summary

    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.

    Features

      • Presents updated and reorganized material that incorporates student feedback
      • Uses an acid–base theme to help students understand the subject rather than simply memorize material
      • Uses an illustrated conceptual approach rather than the presentation of abstracted principles
      • Offers a fully updated and solutions manual as a downloadable PDF file

    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

  • 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