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Organic Chemistry: A Tenth Edition

by John McMurry

Published by OpenStax

ChemistryCollege

John McMurry's Organic Chemistry is renowned as the most clearly written book available for organic chemistry. In John McMurry's words, "I wrote this book because I love writing. I get great pleasure and satisfaction from taking a complicated subject, turning it around until I see it clearly from a new angle, and then explaining it in simple words." In Organic Chemistry: A Tenth Edition from OpenStax, McMurry continues this tradition while updating scientific discoveries, highlighting new applications, scrutinizing every piece of art, and providing example problems to assist students. Organic Chemistry: A Tenth Edition continues to meet the scope and sequence of a two-semester organic chemistry course that follows a functional group approach. A highlighted list of changes along with a detailed table of contents and ancillary descriptions can be found on the Instructor and Student resources sections of this page. John McMurry decided to publish Organic Chemistry: A Tenth Edition under an open license as a tribute to his son, Peter McMurry, who passed away from cystic fibrosis in December 2019. Please click here to learn more about Peter's legacy and to support the fight against cystic fibrosis.

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Attribution

Adapted from Organic Chemistry: A Tenth Edition by John McMurry, published by OpenStax (Rice University) under CC BY-NC-SA 4.0 (https://creativecommons.org/licenses/by-nc-sa/4.0/). Access the original for free at https://openstax.org/details/books/organic-chemistry. Changes: converted to CuraCourse lessons, with interactive practice added.

Table of contents

373 pages in 33 modules. Sign up to read and adopt them.

  1. Dedication and Preface1 page
    1. Dedication and Preface
  2. 1Structure and Bonding14 pages
    1. Why This Chapter?
    2. 1.1Atomic Structure: The Nucleus
    3. 1.2Atomic Structure: Orbitals
    4. 1.3Atomic Structure: Electron Configurations
    5. 1.4Development of Chemical Bonding Theory
    6. 1.5Describing Chemical Bonds: Valence Bond Theory
    7. 1.6sp3 Hybrid Orbitals and the Structure of Methane
    8. 1.7sp3 Hybrid Orbitals and the Structure of Ethane
    9. 1.8sp2 Hybrid Orbitals and the Structure of Ethylene
    10. 1.9sp Hybrid Orbitals and the Structure of Acetylene
    11. 1.10Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur
    12. 1.11Describing Chemical Bonds: Molecular Orbital Theory
    13. 1.12Drawing Chemical Structures
    14. Practice
  3. 2Polar Covalent Bonds; Acids and Bases14 pages
    1. Why This Chapter?
    2. 2.1Polar Covalent Bonds and Electronegativity
    3. 2.2Polar Covalent Bonds and Dipole Moments
    4. 2.3Formal Charges
    5. 2.4Resonance
    6. 2.5Rules for Resonance Forms
    7. 2.6Drawing Resonance Forms
    8. 2.7Acids and Bases: The Brønsted–Lowry Definition
    9. 2.8Acid and Base Strength
    10. 2.9Predicting Acid–Base Reactions from pKa Values
    11. 2.10Organic Acids and Organic Bases
    12. 2.11Acids and Bases: The Lewis Definition
    13. 2.12Noncovalent Interactions between Molecules
    14. Practice
  4. 3Organic Compounds: Alkanes and Their Stereochemistry9 pages
    1. Why This Chapter?
    2. 3.1Functional Groups
    3. 3.2Alkanes and Alkane Isomers
    4. 3.3Alkyl Groups
    5. 3.4Naming Alkanes
    6. 3.5Properties of Alkanes
    7. 3.6Conformations of Ethane
    8. 3.7Conformations of Other Alkanes
    9. Practice
  5. 4Organic Compounds: Cycloalkanes and Their Stereochemistry11 pages
    1. Why This Chapter?
    2. 4.1Naming Cycloalkanes
    3. 4.2Cis–Trans Isomerism in Cycloalkanes
    4. 4.3Stability of Cycloalkanes: Ring Strain
    5. 4.4Conformations of Cycloalkanes
    6. 4.5Conformations of Cyclohexane
    7. 4.6Axial and Equatorial Bonds in Cyclohexane
    8. 4.7Conformations of Monosubstituted Cyclohexanes
    9. 4.8Conformations of Disubstituted Cyclohexanes
    10. 4.9Conformations of Polycyclic Molecules
    11. Practice
  6. 5Stereochemistry at Tetrahedral Centers14 pages
    1. Why This Chapter?
    2. 5.1Enantiomers and the Tetrahedral Carbon
    3. 5.2The Reason for Handedness in Molecules: Chirality
    4. 5.3Optical Activity
    5. 5.4Pasteur’s Discovery of Enantiomers
    6. 5.5Sequence Rules for Specifying Configuration
    7. 5.6Diastereomers
    8. 5.7Meso Compounds
    9. 5.8Racemic Mixtures and the Resolution of Enantiomers
    10. 5.9A Review of Isomerism
    11. 5.10Chirality at Nitrogen, Phosphorus, and Sulfur
    12. 5.11Prochirality
    13. 5.12Chirality in Nature and Chiral Environments
    14. Practice
  7. 6An Overview of Organic Reactions13 pages
    1. Why This Chapter?
    2. 6.1Kinds of Organic Reactions
    3. 6.2How Organic Reactions Occur: Mechanisms
    4. 6.3Polar Reactions
    5. 6.4An Example of a Polar Reaction: Addition of HBr to Ethylene
    6. 6.5Using Curved Arrows in Polar Reaction Mechanisms
    7. 6.6Radical Reactions
    8. 6.7Describing a Reaction: Equilibria, Rates, and Energy Changes
    9. 6.8Describing a Reaction: Bond Dissociation Energies
    10. 6.9Describing a Reaction: Energy Diagrams and Transition States
    11. 6.10Describing a Reaction: Intermediates
    12. 6.11A Comparison Between Biological Reactions and Laboratory Reactions
    13. Practice
  8. 7Alkenes: Structure and Reactivity13 pages
    1. Why This Chapter?
    2. 7.1Industrial Preparation and Use of Alkenes
    3. 7.2Calculating the Degree of Unsaturation
    4. 7.3Naming Alkenes
    5. 7.4Cis–Trans Isomerism in Alkenes
    6. 7.5Alkene Stereochemistry and the E,Z Designation
    7. 7.6Stability of Alkenes
    8. 7.7Electrophilic Addition Reactions of Alkenes
    9. 7.8Orientation of Electrophilic Additions: Markovnikov’s Rule
    10. 7.9Carbocation Structure and Stability
    11. 7.10The Hammond Postulate
    12. 7.11Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements
    13. Practice
  9. 8Alkenes: Reactions and Synthesis15 pages
    1. Why This Chapter?
    2. 8.1Preparing Alkenes: A Preview of Elimination Reactions
    3. 8.2Halogenation of Alkenes: Addition of X2
    4. 8.3Halohydrins from Alkenes: Addition of HO-X
    5. 8.4Hydration of Alkenes: Addition of H2O by Oxymercuration
    6. 8.5Hydration of Alkenes: Addition of H2O by Hydroboration
    7. 8.6Reduction of Alkenes: Hydrogenation
    8. 8.7Oxidation of Alkenes: Epoxidation and Hydroxylation
    9. 8.8Oxidation of Alkenes: Cleavage to Carbonyl Compounds
    10. 8.9Addition of Carbenes to Alkenes: Cyclopropane Synthesis
    11. 8.10Radical Additions to Alkenes: Chain-Growth Polymers
    12. 8.11Biological Additions of Radicals to Alkenes
    13. 8.12Reaction Stereochemistry: Addition of H2O to an Achiral Alkene
    14. 8.13Reaction Stereochemistry: Addition of H2O to a Chiral Alkene
    15. Practice
  10. 9Alkynes: An Introduction to Organic Synthesis11 pages
    1. Why This Chapter?
    2. 9.1Naming Alkynes
    3. 9.2Preparation of Alkynes: Elimination Reactions of Dihalides
    4. 9.3Reactions of Alkynes: Addition of HX and X2
    5. 9.4Hydration of Alkynes
    6. 9.5Reduction of Alkynes
    7. 9.6Oxidative Cleavage of Alkynes
    8. 9.7Alkyne Acidity: Formation of Acetylide Anions
    9. 9.8Alkylation of Acetylide Anions
    10. 9.9An Introduction to Organic Synthesis
    11. Practice
  11. 10Organohalides10 pages
    1. Why This Chapter?
    2. 10.1Names and Structures of Alkyl Halides
    3. 10.2Preparing Alkyl Halides from Alkanes: Radical Halogenation
    4. 10.3Preparing Alkyl Halides from Alkenes: Allylic Bromination
    5. 10.4Stability of the Allyl Radical: Resonance Revisited
    6. 10.5Preparing Alkyl Halides from Alcohols
    7. 10.6Reactions of Alkyl Halides: Grignard Reagents
    8. 10.7Organometallic Coupling Reactions
    9. 10.8Oxidation and Reduction in Organic Chemistry
    10. Practice
  12. 11Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations14 pages
    1. Why This Chapter?
    2. 11.1The Discovery of Nucleophilic Substitution Reactions
    3. 11.2The SN2 Reaction
    4. 11.3Characteristics of the SN2 Reaction
    5. 11.4The SN1 Reaction
    6. 11.5Characteristics of the SN1 Reaction
    7. 11.6Biological Substitution Reactions
    8. 11.7Elimination Reactions: Zaitsev’s Rule
    9. 11.8The E2 Reaction and the Deuterium Isotope Effect
    10. 11.9The E2 Reaction and Cyclohexane Conformation
    11. 11.10The E1 and E1cB Reactions
    12. 11.11Biological Elimination Reactions
    13. 11.12A Summary of Reactivity: SN1, SN2, E1, E1cB, and E2
    14. Practice
  13. 12Structure Determination: Mass Spectrometry and Infrared Spectroscopy10 pages
    1. Why This Chapter?
    2. 12.1Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments
    3. 12.2Interpreting Mass Spectra
    4. 12.3Mass Spectrometry of Some Common Functional Groups
    5. 12.4Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments
    6. 12.5Spectroscopy and the Electromagnetic Spectrum
    7. 12.6Infrared Spectroscopy
    8. 12.7Interpreting Infrared Spectra
    9. 12.8Infrared Spectra of Some Common Functional Groups
    10. Practice
  14. 13Structure Determination: Nuclear Magnetic Resonance Spectroscopy15 pages
    1. Why This Chapter?
    2. 13.1Nuclear Magnetic Resonance Spectroscopy
    3. 13.2The Nature of NMR Absorptions
    4. 13.3Chemical Shifts
    5. 13.4Chemical Shifts in 1H NMR Spectroscopy
    6. 13.5Integration of 1H NMR Absorptions: Proton Counting
    7. 13.6Spin–Spin Splitting in 1H NMR Spectra
    8. 13.71H NMR Spectroscopy and Proton Equivalence
    9. 13.8More Complex Spin–Spin Splitting Patterns
    10. 13.9Uses of 1H NMR Spectroscopy
    11. 13.1013C NMR Spectroscopy: Signal Averaging and FT–NMR
    12. 13.11Characteristics of 13C NMR Spectroscopy
    13. 13.12DEPT 13C NMR Spectroscopy
    14. 13.13Uses of 13C NMR Spectroscopy
    15. Practice
  15. 14Conjugated Compounds and Ultraviolet Spectroscopy11 pages
    1. Why This Chapter?
    2. 14.1Stability of Conjugated Dienes: Molecular Orbital Theory
    3. 14.2Electrophilic Additions to Conjugated Dienes: Allylic Carbocations
    4. 14.3Kinetic versus Thermodynamic Control of Reactions
    5. 14.4The Diels–Alder Cycloaddition Reaction
    6. 14.5Characteristics of the Diels–Alder Reaction
    7. 14.6Diene Polymers: Natural and Synthetic Rubbers
    8. 14.7Ultraviolet Spectroscopy
    9. 14.8Interpreting Ultraviolet Spectra: The Effect of Conjugation
    10. 14.9Conjugation, Color, and the Chemistry of Vision
    11. Practice
  16. 15Benzene and Aromaticity9 pages
    1. Why This Chapter?
    2. 15.1Naming Aromatic Compounds
    3. 15.2Structure and Stability of Benzene
    4. 15.3Aromaticity and the Hückel 4n + 2 Rule
    5. 15.4Aromatic Ions
    6. 15.5Aromatic Heterocycles: Pyridine and Pyrrole
    7. 15.6Polycyclic Aromatic Compounds
    8. 15.7Spectroscopy of Aromatic Compounds
    9. Practice
  17. 16Chemistry of Benzene: Electrophilic Aromatic Substitution12 pages
    1. Why This Chapter?
    2. 16.1Electrophilic Aromatic Substitution Reactions: Bromination
    3. 16.2Other Aromatic Substitutions
    4. 16.3Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction
    5. 16.4Substituent Effects in Electrophilic Substitutions
    6. 16.5Trisubstituted Benzenes: Additivity of Effects
    7. 16.6Nucleophilic Aromatic Substitution
    8. 16.7Benzyne
    9. 16.8Oxidation of Aromatic Compounds
    10. 16.9Reduction of Aromatic Compounds
    11. 16.10Synthesis of Polysubstituted Benzenes
    12. Practice
  18. 17Alcohols and Phenols13 pages
    1. Why This Chapter?
    2. 17.1Naming Alcohols and Phenols
    3. 17.2Properties of Alcohols and Phenols
    4. 17.3Preparation of Alcohols: A Review
    5. 17.4Alcohols from Carbonyl Compounds: Reduction
    6. 17.5Alcohols from Carbonyl Compounds: Grignard Reaction
    7. 17.6Reactions of Alcohols
    8. 17.7Oxidation of Alcohols
    9. 17.8Protection of Alcohols
    10. 17.9Phenols and Their Uses
    11. 17.10Reactions of Phenols
    12. 17.11Spectroscopy of Alcohols and Phenols
    13. Practice
  19. 18Ethers and Epoxides; Thiols and Sulfides10 pages
    1. Why This Chapter?
    2. 18.1Names and Properties of Ethers
    3. 18.2Preparing Ethers
    4. 18.3Reactions of Ethers: Acidic Cleavage
    5. 18.4Cyclic Ethers: Epoxides
    6. 18.5Reactions of Epoxides: Ring-Opening
    7. 18.6Crown Ethers
    8. 18.7Thiols and Sulfides
    9. 18.8Spectroscopy of Ethers
    10. Practice
  20. 19Aldehydes and Ketones: Nucleophilic Addition Reactions16 pages
    1. Why This Chapter?
    2. 19.1Naming Aldehydes and Ketones
    3. 19.2Preparing Aldehydes and Ketones
    4. 19.3Oxidation of Aldehydes and Ketones
    5. 19.4Nucleophilic Addition Reactions of Aldehydes and Ketones
    6. 19.5Nucleophilic Addition of H2O: Hydration
    7. 19.6Nucleophilic Addition of HCN: Cyanohydrin Formation
    8. 19.7Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation
    9. 19.8Nucleophilic Addition of Amines: Imine and Enamine Formation
    10. 19.9Nucleophilic Addition of Hydrazine: The Wolff–Kishner Reaction
    11. 19.10Nucleophilic Addition of Alcohols: Acetal Formation
    12. 19.11Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction
    13. 19.12Biological Reductions
    14. 19.13Conjugate Nucleophilic Addition to α,β‑Unsaturated Aldehydes and Ketones
    15. 19.14Spectroscopy of Aldehydes and Ketones
    16. Practice
  21. 20Carboxylic Acids and Nitriles10 pages
    1. Why This Chapter?
    2. 20.1Naming Carboxylic Acids and Nitriles
    3. 20.2Structure and Properties of Carboxylic Acids
    4. 20.3Biological Acids and the Henderson–Hasselbalch Equation
    5. 20.4Substituent Effects on Acidity
    6. 20.5Preparing Carboxylic Acids
    7. 20.6Reactions of Carboxylic Acids: An Overview
    8. 20.7Chemistry of Nitriles
    9. 20.8Spectroscopy of Carboxylic Acids and Nitriles
    10. Practice
  22. 21Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions12 pages
    1. Why This Chapter?
    2. 21.1Naming Carboxylic Acid Derivatives
    3. 21.2Nucleophilic Acyl Substitution Reactions
    4. 21.3Reactions of Carboxylic Acids
    5. 21.4Chemistry of Acid Halides
    6. 21.5Chemistry of Acid Anhydrides
    7. 21.6Chemistry of Esters
    8. 21.7Chemistry of Amides
    9. 21.8Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives
    10. 21.9Polyamides and Polyesters: Step-Growth Polymers
    11. 21.10Spectroscopy of Carboxylic Acid Derivatives
    12. Practice
  23. 22Carbonyl Alpha-Substitution Reactions9 pages
    1. Why This Chapter?
    2. 22.1Keto–Enol Tautomerism
    3. 22.2Reactivity of Enols: α-Substitution Reactions
    4. 22.3Alpha Halogenation of Aldehydes and Ketones
    5. 22.4Alpha Bromination of Carboxylic Acids
    6. 22.5Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation
    7. 22.6Reactivity of Enolate Ions
    8. 22.7Alkylation of Enolate Ions
    9. Practice
  24. 23Carbonyl Condensation Reactions15 pages
    1. Why This Chapter?
    2. 23.1Carbonyl Condensations: The Aldol Reaction
    3. 23.2Carbonyl Condensations versus Alpha Substitutions
    4. 23.3Dehydration of Aldol Products: Synthesis of Enones
    5. 23.4Using Aldol Reactions in Synthesis
    6. 23.5Mixed Aldol Reactions
    7. 23.6Intramolecular Aldol Reactions
    8. 23.7The Claisen Condensation Reaction
    9. 23.8Mixed Claisen Condensations
    10. 23.9Intramolecular Claisen Condensations: The Dieckmann Cyclization
    11. 23.10Conjugate Carbonyl Additions: The Michael Reaction
    12. 23.11Carbonyl Condensations with Enamines: The Stork Enamine Reaction
    13. 23.12The Robinson Annulation Reaction
    14. 23.13Some Biological Carbonyl Condensation Reactions
    15. Practice
  25. 24Amines and Heterocycles12 pages
    1. Why This Chapter?
    2. 24.1Naming Amines
    3. 24.2Structure and Properties of Amines
    4. 24.3Basicity of Amines
    5. 24.4Basicity of Arylamines
    6. 24.5Biological Amines and the Henderson–Hasselbalch Equation
    7. 24.6Synthesis of Amines
    8. 24.7Reactions of Amines
    9. 24.8Reactions of Arylamines
    10. 24.9Heterocyclic Amines
    11. 24.10Spectroscopy of Amines
    12. Practice
  26. 25Biomolecules: Carbohydrates12 pages
    1. Why This Chapter?
    2. 25.1Classification of Carbohydrates
    3. 25.2Representing Carbohydrate Stereochemistry: Fischer Projections
    4. 25.3D,L Sugars
    5. 25.4Configurations of the Aldoses
    6. 25.5Cyclic Structures of Monosaccharides: Anomers
    7. 25.6Reactions of Monosaccharides
    8. 25.7The Eight Essential Monosaccharides
    9. 25.8Disaccharides
    10. 25.9Polysaccharides and Their Synthesis
    11. 25.10Some Other Important Carbohydrates
    12. Practice
  27. 26Biomolecules: Amino Acids, Peptides, and Proteins13 pages
    1. Why This Chapter?
    2. 26.1Structures of Amino Acids
    3. 26.2Amino Acids and the Henderson–Hasselbalch Equation: Isoelectric Points
    4. 26.3Synthesis of Amino Acids
    5. 26.4Peptides and Proteins
    6. 26.5Amino Acid Analysis of Peptides
    7. 26.6Peptide Sequencing: The Edman Degradation
    8. 26.7Peptide Synthesis
    9. 26.8Automated Peptide Synthesis: The Merrifield Solid-Phase Method
    10. 26.9Protein Structure
    11. 26.10Enzymes and Coenzymes
    12. 26.11How Do Enzymes Work? Citrate Synthase
    13. Practice
  28. 27Biomolecules: Lipids9 pages
    1. Why This Chapter?
    2. 27.1Waxes, Fats, and Oils
    3. 27.2Soap
    4. 27.3Phospholipids
    5. 27.4Prostaglandins and Other Eicosanoids
    6. 27.5Terpenoids
    7. 27.6Steroids
    8. 27.7Biosynthesis of Steroids
    9. Practice
  29. 28Biomolecules: Nucleic Acids10 pages
    1. Why This Chapter?
    2. 28.1Nucleotides and Nucleic Acids
    3. 28.2Base Pairing in DNA
    4. 28.3Replication of DNA
    5. 28.4Transcription of DNA
    6. 28.5Translation of RNA: Protein Biosynthesis
    7. 28.6DNA Sequencing
    8. 28.7DNA Synthesis
    9. 28.8The Polymerase Chain Reaction
    10. Practice
  30. 29The Organic Chemistry of Metabolic Pathways12 pages
    1. Why This Chapter?
    2. 29.1An Overview of Metabolism and Biochemical Energy
    3. 29.2Catabolism of Triacylglycerols: The Fate of Glycerol
    4. 29.3Catabolism of Triacylglycerols: β-Oxidation
    5. 29.4Biosynthesis of Fatty Acids
    6. 29.5Catabolism of Carbohydrates: Glycolysis
    7. 29.6Conversion of Pyruvate to Acetyl CoA
    8. 29.7The Citric Acid Cycle
    9. 29.8Carbohydrate Biosynthesis: Gluconeogenesis
    10. 29.9Catabolism of Proteins: Deamination
    11. 29.10Some Conclusions about Biological Chemistry
    12. Practice
  31. 30Orbitals and Organic Chemistry: Pericyclic Reactions11 pages
    1. Why This Chapter?
    2. 30.1Molecular Orbitals of Conjugated Pi Systems
    3. 30.2Electrocyclic Reactions
    4. 30.3Stereochemistry of Thermal Electrocyclic Reactions
    5. 30.4Photochemical Electrocyclic Reactions
    6. 30.5Cycloaddition Reactions
    7. 30.6Stereochemistry of Cycloadditions
    8. 30.7Sigmatropic Rearrangements
    9. 30.8Some Examples of Sigmatropic Rearrangements
    10. 30.9A Summary of Rules for Pericyclic Reactions
    11. Practice
  32. 31Synthetic Polymers9 pages
    1. Why This Chapter?
    2. 31.1Chain-Growth Polymers
    3. 31.2Stereochemistry of Polymerization: Ziegler–Natta Catalysts
    4. 31.3Copolymers
    5. 31.4Step-Growth Polymers
    6. 31.5Olefin Metathesis Polymerization
    7. 31.6Intramolecular Olefin Metathesis
    8. 31.7Polymer Structure and Physical Properties
    9. Practice
  33. Appendices4 pages
    1. ANomenclature of Polyfunctional Organic Compounds
    2. BAcidity Constants for Some Organic Compounds
    3. CGlossary
    4. DPeriodic Table