Organic Chemistry - 1st Edition - ISBN: 9780128007808, 9780128010822

Organic Chemistry

1st Edition

Structure, Mechanism, and Synthesis

Authors: Robert Ouellette J. David Rawn
eBook ISBN: 9780128010822
Hardcover ISBN: 9780128007808
Imprint: Elsevier
Published Date: 20th June 2014
Page Count: 1240
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Description

Organic Chemistry provides a comprehensive discussion of the basic principles of organic chemistry in their relation to a host of other fields in both physical and biological sciences. This book is written based on the premise that there are no shortcuts in organic chemistry, and that understanding and mastery cannot be achieved without devoting adequate time and attention to the theories and concepts of the discipline. It lays emphasis on connecting the basic principles of organic chemistry to real world challenges that require analysis, not just recall.

This text covers topics ranging from structure and bonding in organic compounds to functional groups and their properties; identification of functional groups by infrared spectroscopy; organic reaction mechanisms; structures and reactions of alkanes and cycloalkanes; nucleophilic substitution and elimination reactions; conjugated alkenes and allylic systems; electrophilic aromatic substitution; carboxylic acids; and synthetic polymers. Throughout the book, principles logically evolve from one to the next, from the simplest to the most complex examples, with abundant connections between the text and real world applications. There are extensive examples of biological relevance, along with a chapter on organometallic chemistry not found in other standard references.

This book will be of interest to chemists, life scientists, food scientists, pharmacists, and students in the physical and life sciences.

Key Features

  • Contains extensive examples of biological relevance
  • Includes an important chapter on organometallic chemistry not found in other standard references
  • Extended, illustrated glossary
  • Appendices on thermodynamics, kinetics, and transition state theory

Readership

Chemists, life scientists, food scientists, pharmacists, students in the physical and life sciences

Table of Contents

  • Dedication
  • Acknowledgments
  • Preface
  • 1: Structure and Bonding in Organic Compounds
    • 1.1 Brief Review of Atomic Structure
    • 1.2 Atomic Properties
    • 1.3 Ionic and Covalent Bonds
    • 1.4 Strategies for Writing Lewis Structures
    • 1.5 Formal Charge
    • 1.6 Molecular Geometry
    • 1.7 Resonance Structures
    • 1.8 Valence Shell Electron Pair Repulsion Theory
    • 1.9 Dipole Moments
    • 1.10 Molecular Orbital Theory
    • 1.11 The Hydrogen Molecule
    • 1.12 Bonding in Carbon Compounds
    • 1.13 sp3 Hybridization of Carbon in Methane
    • 1.14 sp3 Hybridization of Carbon in Ethane
    • 1.15 sp2 Hybridization of Carbon in Ethene
    • 1.16 sp Hybridization of Carbon in Ethyne
    • 1.17 Effect of Hybridization on Bond Length and Bond Strength
    • 1.18 Hybridization of Nitrogen
    • 1.19 Hybridization of Oxygen
    • Exercises
  • 2: Part I: Functional Groups and Their Properties
    • 2.1 Introduction to Functional Groups: Hydrocarbons and Haloalkanes
    • 2.2 Functional Groups that Contain Oxygen
    • 2.3 Functional Groups that Contain Nitrogen
    • 2.4 Functional Groups that Contain Sulfur
    • 2.5 Structural Formulas
    • 2.6 Bond-Line Structures
    • 2.7 Isomers
    • Part II: Identification of Functional Groups by Infrared Spectroscopy
    • 2.8 Spectroscopy
    • 2.9 Infrared Spectroscopy
    • 2.10 Identifying Hydrocarbons
    • 2.11 Identifying Oxygen-Containing Compounds
    • 2.12 Identifying Nitrogen-Containing Compounds
    • 2.13 Bending Deformations
    • End-of-Chapter Exercises
  • 3: Introduction to Organic Reaction Mechanisms
    • 3.1 Acid–Base reaction
    • 3.2 Chemical Equilibrium and Equilibrium Constants
    • 3.3 pH and pK Values
    • 3.4 Effect of Structure on Acidity
    • 3.5 Standard Free Energy Changes in Chemical Reactions
    • 3.6 Enthalpy Changes in Chemical Reactions
    • 3.7 Bond Dissociation Energies
    • 3.8 Introduction to Reaction Mechanisms
    • 3.9 Structures and Stabilities Of Carbon Radicals, Carbocations, and Carbanions
    • 3.10 Factors that influence reaction rates
    • 3.11 Reaction Rate Theory
    • 3.12 Stability and reactivity
    • End-of-Chapter Exercises
  • 4: Alkanes and Cycloalkanes: Structures and Reactions
    • 4.1 Classes of Hydrocarbons
    • 4.2 Alkanes
    • 4.3 Nomenclature of Alkanes
    • 4.4 Conformation of Alkanes
    • 4.5 Cycloalkanes
    • 4.6 Conformations of cycloalkanes
    • 4.7 Conformational Mobility of cyclohexane
    • 4.8 Monosubstituted Cyclohexanes
    • 4.9 Disubstituted Cyclohexanes
    • 4.10 Polycyclic Molecules
    • 4.11 Physical Properties of Alkanes
    • 4.12 Stabilities of Alkyl Radicals
    • 4.13 Chlorination of an Alkane–A Radical Reaction
    • Exercises
  • 5: Alkenes Structures and Properties
    • 5.1 Alkenes
    • 5.2 Structure and Bonding of Alkenes
    • 5.3 Unsaturation Number
    • 5.4 Geometric Isomerism
    • 5.5 E,Z Nomenclature of Geometrical Isomers
    • 5.6 Nomenclature of Alkenes
    • 5.7 Physical Properties of Alkenes
    • 5.8 Stability of Alkenes
    • 5.9 Reduction of Alkenes
    • 5.10 Mechanism of Catalytic Hydrogenation
    • 5.11 Heats of hydrogenation of alkenes
    • Exercise
  • 6: Alkenes: Addition Reactions
    • 6.1 Characteristics of Addition Reactions
    • 6.2 Addition of Hydrogen Halides to Alkenes
    • 6.3 The Mechanistic Basis of Markovnikov's Rule
    • 6.4 Carbocation Rearrangement Reactions
    • 6.5 Hydration of Alkenes
    • 6.6 Addition of Halogens
    • 6.7 Addition of Carbenes
    • 6.8 Epoxidation of Alkenes
    • 6.9 Dihydroxylatin of Alkenes
    • 6.10 Ozonolysis of Alkenes
    • Exercises
  • 7: Alkynes
    • 7.1 Occurrence and Uses of Alkynes
    • 7.2 Structure and Properties of Alkynes
    • 7.3 IUPAC Names of Alkynes
    • 7.4 Acidity of Terminal Alkynes
    • 7.5 Hydrogenation of Alkynes
    • 7.6 Electrophilic Addition Reactions
    • 7.7 Synthesis of Alkynes
    • Exercises
  • 8: Stereochemistry
    • 8.1 Stereoisomers
    • 8.2 Mirror Image Objects, Mirror Image Molecules, and Chirality
    • 8.3 Optical Activity
    • 8.4 Fischer Projection Formulas
    • 8.5 Absolute Configuration
    • 8.6 Molecules with Two (or More) Stereogenic Centers
    • 8.7 Cyclic Molecules with Stereogenic Centers
    • 8.8 Separation of Enantiomers
    • 8.9 Chemical Reactions at Stereogenic Centers
    • 8.10 Reactions that Produce Stereogenic Centers
    • 8.11 Reactions that Form Diastereomers
    • 8.12 Prochiral Centers
    • Exercises
  • 9: Haloalkanes and Alcohols: Introduction to Nucleophilic Substitution and Elimination Reactions
    • 9.1 Functionalized Hydrocarbons
    • 9.2 Nomenclature of Haloalkanes
    • 9.3 Nomenclature of Alcohols
    • 9.4 Structure and Properties of Haloalkanes
    • 9.5 Structure and Properties of Alcohols
    • 9.6 Organometallic Compounds
    • 9.7 Reactions of Haloalkanes
    • 9.8 Nucleophilic Substitution Reactions of Haloalkanes
    • 9.9 Mechanisms of Nucleophilic Substitution Reactions of Haloalkanes
    • 9.10 Reactions of Alcohols
    • 9.11 Acid–Base Reactions of Alcohols
    • 9.12 Substitution Reactions of Alcohols
    • 9.13 Alternate Methods for the Synthesis of Alkyl Halides
    • 9.14 Elimination Reactions
    • 9.15 Regioselectivity in Dehydrohalogenation
    • 9.16 Mechanisms of Dehydrohalogenation Reactions
    • 9.17 Regioselectivity in Dehydration Reactions
    • Exercises
  • 10: Nucleophilic Substitution and Elimination Reactions
    • 10.1 Properties of Nucleophiles
    • 10.2 Biological SN2 Reactions Bysulfur-Containing Nucleophiles
    • 10.3 Stereochemistry of Nucleophilic Substitution Reactions
    • 10.4 SN1 Versus SN2 Reactions
    • 10.5 Mechanisms of Elimination Reactions
    • 10.6 Effects of Structure on Competing Substitution and Elimination Reactions
    • Exercises
  • 11: Conjugated Alkenes and Allylic Systems
    • 11.1 Classes of Dienes
    • 11.2 Stability of Conjugated Dienes
    • 11.3 Molecular Orbitals of Ethene and 1,3-Butadiene
    • 11.4 Structural Effects of Conjugation in 1,3-Butadiene
    • 11.5 Allylic Systems
    • 11.6 Hückel Molecular Orbitals of Allyl Systems
    • 11.7 Electrophilic Addition to Conjugated Dienes
    • 11.8 The Diels-Alder Reaction
    • 11.9 The Electromagnetic Spectrum
    • 11.10 Ultraviolet-Visible Spectroscopy of Alkenes and Conjugated Systems
    • Exercises
  • 12: Arenes and Aromaticity
    • 12.1 Aromatic Compounds
    • 12.2 The Covalent Structure of Benzene
    • 12.3 The Hückel Rule
    • 12.4 Molecular Orbitals of Aromatic and Antiaromatic Compounds
    • 12.5 Heterocyclic Aromatic Compounds
    • 12.6 Polycyclic Aromatic Compounds
    • Exercises
  • 13: Electrophilic Aromatic Substitution
    • 13.1 Nomenclature of Benzene Derivatives
    • 13.2 Mechanism of Electrophilic Aromatic Substitution
    • 13.3 Common Electrophilic Aromatic Substitution Reactions
    • 13.4 Substituent Effects on the Reactivity of Benzene Rings
    • 13.5 Interpretation of the Effect of Substituents on Reaction Rates
    • 13.6 Interpretation of Directing Effects
    • 13.7 Functional Group Modification
    • 13.8 Synthesis of Substituted Aromatic Compounds
    • Exercises
  • 14: Methods for Structure Determination Nuclear Magnetic Resonance and Mass Spectrometry
    • 14.1 structure determination
    • 14.2 Nuclear Magnetic Resonance Spectroscopy
    • 14.3 The Chemical Shift
    • 14.4 Detecting Sets of Nonequivalent Hydrogen Atoms
    • 14.5 Effects of Structure on Chemical Shift
    • 14.6 Relative Peak Areas and Proton Counting
    • 14.7 Spin–Spin Splitting
    • 14.8 Effect of Structure on Coupling Constants
    • 14.9 Effect of Dynamic Processes
    • 14.10 Carbon-13 NMR Spectroscopy
    • 14.11 Introduction to Mass Spectrometry
    • Exercises
  • 15: Alcohols: Reactions and Synthesis
    • 15.1 Overview of Alcohol Reactions
    • 15.2 Converting Alcohols into Esters
    • 15.3 Conversion of Alcohols to Haloalkanes
    • 15.4 Oxidation of Alcohols
    • 15.5 Reactions of Vicinal Diols
    • 15.6 Synthesis of Alcohols
    • 15.7 Synthesis of Alcohols from Haloalkanes
    • 15.8 Indirect Hydration Methods
    • 15.9 Reduction of Carbonyl Compounds
    • 15.10 Alcohol Synthesis Using Grignard Reagents
    • 15.11 Thiols and Thioethers
    • Exercises
  • 16: Ethers and Epoxides
    • 16.1 Structure of Ethers
    • 16.2 Nomenclature of Ethers
    • 16.3 Physical Properties of Ethers
    • 16.4 Polyether Antibiotics
    • 16.5 Synthesis of Ethers: Alkoxymercuration-Demercuration of Alkenes
    • 16.6 The Williamson Ether Synthesis
    • 16.7 Reactions of Ethers
    • 16.8 Ethers as Protecting Groups
    • 16.9 Synthesis of Epoxides
    • 16.10 Reactions of Epoxides
    • 16.11 Sulfides
    • 16.12 Spectroscopy of Ethers, Thiols, and Sulfides
    • Exercises
  • 17: Organometallic Chemistry of Transition Metal Elements and Introduction to Retrosynthesis
    • 17.1 Brief Overview of Transition Metal Complexes
    • 17.2 The Gilman Reagent
    • 17.3 Overview of Palladiumcatalyzed Cross-Coupling Reactions
    • 17.4 The Suzuki Coupling Reaction
    • 17.5 The Heck Reaction
    • 17.6 The Sonogashira Reaction
    • 17.7 The Wilkinson Catalyst: Homogeneous Catalytic Hydrogenation
    • 17.8 Asymmetric Hydrogenation with Chiral Ruthenium Catalysts
    • 17.9 The Grubbs Reaction: A Metathesis Reaction for Alkene Synthesis
    • 17.9 Introduction to Retrosynthesis: Thinking Backwards
    • Exercises
  • 18: Aldehydes and Ketones
    • 18.1 The Carbonyl Group
    • 18.2 Nomenclature of Aldehydes and Ketones
    • 18.3 Physical Properties of Aldehydes and Ketones
    • 18.4 Oxidation–Reduction Reactions of Carbonyl Compounds
    • 18.5 Synthesis of Carbonyl Compounds: A Review
    • 18.6 Carbonyl Compounds: A Preview
    • 18.7 Spectroscopy of Aldehydes and Ketones
    • Exercises
  • 19: Aldehydes and Ketones: Nucleophilic Addition Reactions
    • 19.1 Relative Stabilities of Aldehydes and Ketones
    • 19.2 Formation of Cyanohydrins
    • 19.3 Hydration of Carbonyl Compounds
    • 19.4 Mechanisms of Acid- and Base-Catalyzed Carbonyl Addition Reactions
    • 19.5 Formation of Acetals and Ketals
    • 19.6 Acetals as Protecting Groups
    • 19.7 Thioacetals and Thioketals
    • 19.8 Addition of Nitrogen Compounds to Aldehydes and Ketones
    • 19.9 The Wittig Reaction
    • Exercises
  • 20: Carboxylic Acids
    • 20.1 Carboxylic Acids and Acyl Groups
    • 20.2 Nomenclature of Carboxylic Acids
    • 20.3 Physical Properties of Carboxylic Acids
    • 20.4 Acidity of Carboxylic Acids
    • 20.5 Carboxylate Anions
    • 20.6 Synthesis of Carboxylic Acids
    • 20.7 Reduction of Carboxylic Acids
    • 20.8 Decarboxylation Reactions
    • 20.9 Reactions of Carboxylic Acids and Their Derivatives: A Preview
    • 20.10 Conversion of Carboxylic Acids into Acyl Halides
    • 20.11 Conversion of Carboxylic Acids into Esters
    • 20.12 Mechanism of Esterification
    • 20.13 Brief Synthetic Review
    • 20.14 Spectroscopy of Carboxylic Acids
    • Exercises
  • 21: Carboxylic Acid Derivatives
    • 21.1 Nomenclature of Carboxylic Acid Derivatives
    • 21.2 Physical Properties of Acyl Derivatives
    • 21.3 Basicity of Carboxylic Acid Derivatives
    • 21.4 Mechanism of Nucleophilic Acyl Substitution
    • 21.5 Hydrolysis of Acyl Derivatives
    • 21.6 Reaction of Acyl Derivatives with Alcohols
    • 21.7 Reaction of Acyl Derivatives with Amines
    • 21.8 Reduction of Acyl Derivatives
    • 21.9 Reaction of Acyl Derivatives with Organometallic Reagents
    • 21.10 Infrared Spectroscopy of Acyl derivatives
    • 21.11 NMR Spectroscopy of Acyl Derivatives
    • Exercises
  • 22: Condensation Reactions of Carbonyl Compounds
    • 22.1 The α-Carbon Atom of Aldehydes and Ketones
    • 22.2 Keto–Enol Equilibria of Aldehydes and Ketones
    • 22.3 Consequences of Enolization
    • 22.4 α-Halogenation Reactions of Aldehydes and Ketones
    • 22.5 Alkylation of Enolate Ions
    • 22.6 The Aldol Condensation of Aldehydes
    • 22.7 Mixed Aldol Condensation Reactions
    • 22.8 Intramolecular Aldol Condensation Reactions
    • 22.9 Conjugation in α-β-Unsaturated Aldehydes and Ketones
    • 22.10 Conjugate Addition Reactions
    • 22.11 The Michael Reaction and Robinson Annulation
    • 22.12 The α-Hydrogen Atoms of Acid Derivatives
    • 22.13 Reaction at the α-Carbon of Acid Derivatives
    • 22.14 The Claisen Condensation
    • 22.15 Aldol-Type Condensations of Acid Derivations
    • 22.16 β -Dicarbonyl Compounds in Synthesis
    • 22.17 Michael Condensations of Acid Derivatives
    • Exercises
  • 23: Amines and Amides
    • 23.1 Organic Nitrogen Compounds
    • 23.2 Bonding and Structure of Amines
    • 23.3 Classification and Nomenclature of Amines
    • 23.4 Physical Properties of Amines
    • 23.5 Basicity of Amines
    • 23.6 Solubility of Ammonium Salts
    • 23.7 Synthesis of Amines by Substitution Reactions
    • 23.8 Synthesis of Amines by Reduction
    • 23.9 The Hofmann Rearrangement
    • 23.10 Overview of Amine Reactions
    • 23.11 Enamines
    • 23.12 Sulfonamides
    • 23.13 Quaternary Ammonium Salts
    • 23.14 spectroscopy of amines
    • Exercises
  • 24: Aryl Halides, Phenols, and Anilines
    • 24.1 Properties of Aromatic Compounds
    • 24.2 Acid-Base Properties of Phenols and Anilines
    • 24.3 Converting Aryl Halides to Grignard Reagents and Organolithium Reagents
    • 24.4 Nucleophilic Aromatic Substitution
    • 24.5 An Overview of Phenol Reactions
    • 24.6 Reactions of Phenoxide Ions
    • 24.7 Quinones
    • 24.8 Substitution Reactions of Aryldiazonium Salts
    • 24.9 Azo Compounds
    • Exercises
  • 25: Pericyclic Reactions
    • 25.1 Concerted Reactions
    • 25.2 Classification of Pericyclic Reactions
    • 25.3 Molecular Orbitals in Pericyclic Reactions
    • 25.4 Eiectrocyclic Reactions
    • 25.5 Cycloaddition Reactions
    • 25.6 Sigmatropic Rearrangements
    • Exercises
  • 26: Carbohydrates
    • 26.1 Carbohydrates in the Biosphere
    • 26.2 Classification of Carbohydrates
    • 26.3 Chirality of Monosaccharides
    • 26.4 Isomerizations of Monosaccharides
    • 26.5 Cyclic Monosaccharides: Hemiacetals and Hemiketals
    • 26.6 Reduction and Oxidation of Monosaccharides
    • 26.7 Glocosides
    • 26.8 Disaccharides
    • 26.9 Polysaccharides
    • 26.10 Chemical Determination of Monsoaccharide Structures
    • 26.11 Determination of Ring Size
    • 26.12 Structure of Disaccharides
    • 26.13 Human Blood Group Antigens
    • Exercises
  • 27: Amino Acids, Peptides, and Proteins
    • 27.1 The Structures of α-Amino Acids
    • 27.2 Acid-Base Equilibria of α-Amino Acids
    • 27.3 Isoionic Point and Titration of α-Amino Acids
    • 27.4 Synthesis of α-Amino Acids
    • 27.5 Chiral Synthesis of α-Amino Acids
    • 27.6 Reactions of α-Amino Acids
    • 27.7 Peptides
    • 27.8 Overview of Peptide Synthesis
    • 27.9 Solid-Phase Peptide Synthesis
    • 27.10 Determination of the Amino Acid Composition of Proteins
    • 27.11 Determination of the Amino Acid Sequence of Proteins
    • 27.12 Bonding in Proteins
    • 27.13 Protein Structure
    • 27.14 Oxygen Storage and Transport: Myoglobin and Hemoglobin
    • Exercises
  • 28: Synthetic Polymers
    • 28.1 Natural and Synthetic Polymers
    • 28.2 Physical Properties of Polymers
    • 28.3 Classes of Polymers
    • 28.4 Polymerization Methods
    • 28.5 Addition Polymerization
    • 28.6 Copolymerization of Alkenes
    • 28.7 Cross-Linked Polymers
    • 28.8 Stereochemistry of Addition Polymerization
    • 28.9 Condensation Polymers
    • 28.10 Polyesters
    • 28.11 Polycarbonates
    • 28.12 Polyamides
    • 28.13 Phenol-Formaldehyde Polymers
    • 28.14 Polyurethanes
    • Exercises
  • Appendix pKa Values
  • Appendix A: Heats of Formation (kJ mole− 1)
  • Appendix IR Absorptions (cm− 1)
  • Appendix 1H NMR and 13C NMR Chemical Shifts (ppm)
  • Glossary
  • A Brief Overview of Thermodynamics
    • 1 First Law of Thermodynamics
    • 2 Estimating ∆H°rxn from Bond Energies
    • 3 Second Law of Thermodynamics
    • 3 Entropy changes in chemical reactions
    • 3 Free Energy
    • 4 Contributions of ΔH°rxn and ΔS°rxn to ΔG°rxn
  • Chemical Kinetics
    • 1 Practical Kinetics
    • 2 Transition State Theory
    • 3 The Hammond Postulate
  • Summary of Synthetic Methods
  • Solutions to In-Chapter Problems
    • Chapter 1
    • Chapter 2
    • Chapter 3
    • Chapter 4
    • Chapter 5
    • Chapter 6
    • Chapter 7
    • Chapter 8
    • Chapter 9
    • Chapter 10
    • Chapter 11
    • Chapter 12
    • Chapter 13
    • Chapter 14
    • Chapter 15
    • Chapter 16
    • Chapter 17
    • Chapter 18
    • Chapter 19
    • Chapter 20
    • Chapter 21
    • Chapter 22
    • Chapter 22
    • Chapter 24
    • Chapter 25
    • Chapter 26
    • Chapter 27
    • Chapter 28
  • Index

Details

No. of pages:
1240
Language:
English
Copyright:
© Elsevier 2014
Published:
Imprint:
Elsevier
eBook ISBN:
9780128010822
Hardcover ISBN:
9780128007808

About the Author

Robert Ouellette

Affiliations and Expertise

Emeritus Professor, The Ohio State University, Columbus, OH, USA

J. David Rawn

Affiliations and Expertise

Towson University, Baltimore, MD, USA

Reviews

"...a good investment for undergraduate students studying organic, medicinal or biological chemistry...should also be appealing to those who teach organic chemistry at undergraduate level."-Education in Chemistry, Nov,14-2014