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Overview
Title: CHEM 231: Organic Chemistry I Textbook
Webpages: 265
Applicable Restrictions: Noncommercial
All licenses found:
- CC BY-NC-SA 4.0: 85.3% (226 pages)
- Undeclared: 10.9% (29 pages)
- CC BY-SA 4.0: 1.5% (4 pages)
- CC BY 4.0: 1.5% (4 pages)
- CC BY-NC-SA 3.0: 0.4% (1 page)
- CC BY-NC 4.0: 0.4% (1 page)
By Page
- CHEM 231: Organic Chemistry I Textbook -
CC BY-SA 4.0
- Front Matter - Undeclared
- 1: Structure and Bonding -
CC BY-NC-SA 4.0
- 1.1: Why This Chapter? - CC BY-NC-SA 4.0
- 1.2: Atomic Structure - The Nucleus - CC BY-NC-SA 4.0
- 1.3: Atomic Structure - Orbitals - CC BY-NC-SA 4.0
- 1.4: Atomic Structure - Electron Configurations - CC BY-NC-SA 4.0
- 1.5: Development of Chemical Bonding Theory - CC BY-NC-SA 4.0
- 1.6: Describing Chemical Bonds - Valence Bond Theory - CC BY-NC-SA 4.0
- 1.7: sp³ Hybrid Orbitals and the Structure of Methane - CC BY-NC-SA 4.0
- 1.8: sp³ Hybrid Orbitals and the Structure of Ethane - CC BY-NC-SA 4.0
- 1.9: sp² Hybrid Orbitals and the Structure of Ethylene - CC BY-NC-SA 4.0
- 1.10: sp Hybrid Orbitals and the Structure of Acetylene - CC BY-NC-SA 4.0
- 1.11: Hybridization of Nitrogen, Oxygen, Phosphorus and Sulfur - CC BY-NC-SA 4.0
- 1.12: Describing Chemical Bonds - Molecular Orbital Theory - CC BY-NC-SA 4.0
- 1.13: The Shapes of Molecules - CC BY-NC-SA 3.0
- 1.14: Drawing Chemical Structures - CC BY-NC-SA 4.0
- 1.15: Chemistry Matters—Organic Foods- Risk versus Benefit - CC BY-NC-SA 4.0
- 1.16: Structure and Bonding (Summary) - Undeclared
- 1.17: Additional Problems - CC BY-NC-SA 4.0
- 2: Polar Covalent Bonds; Acids and Bases -
CC BY-NC-SA 4.0
- 2.1: Why This Chapter? - CC BY-NC-SA 4.0
- 2.2: Polar Covalent Bonds - Electronegativity - CC BY-NC-SA 4.0
- 2.3: Polar Covalent Bonds - Dipole Moments - CC BY-NC-SA 4.0
- 2.4: Intermolecular Forces - CC BY-NC-SA 4.0
- 2.5: Physical Properties of Organic Compounds - Undeclared
- 2.6: Formal Charges - CC BY-NC-SA 4.0
- 2.7: Resonance - CC BY-NC-SA 4.0
- 2.8: Rules for Resonance Forms - CC BY-NC-SA 4.0
- 2.9: Drawing Resonance Forms - CC BY-NC-SA 4.0
- 2.10: Acids and Bases - The Brønsted-Lowry Definition - CC BY-NC-SA 4.0
- 2.11: Acid and Base Strength - CC BY-NC-SA 4.0
- 2.12: Predicting Acid-Base Reactions from pKa Values - CC BY-NC-SA 4.0
- 2.13: Structural Effects on Acidity and Basicity - CC BY-NC-SA 4.0
- 2.14: Organic Acids and Organic Bases - CC BY-NC-SA 4.0
- 2.15: Acids and Bases - The Lewis Definition - CC BY-NC-SA 4.0
- 2.16: Chemistry Matters—Alkaloids- From Cocaine to Dental Anesthetics - CC BY-NC-SA 4.0
- 2.17: Polar Covalent Bonds; Acids and Bases (Summary) - Undeclared
- 2.18: Additional Problems - CC BY-NC-SA 4.0
- 3: Organic Compounds- Functional Groups and Nomenclature -
CC BY-NC-SA 4.0
- 3.1: Why This Chapter? - CC BY-NC-SA 4.0
- 3.2: Functional Groups - CC BY-NC-SA 4.0
- 3.3: Alkanes and Alkane Isomers - CC BY-NC-SA 4.0
- 3.4: Alkyl Groups - CC BY-NC-SA 4.0
- 3.5: Naming Alkanes - CC BY-NC-SA 4.0
- 3.6: Naming Cycloalkanes - CC BY-NC-SA 4.0
- 3.7: Alkyl Substituents - CC BY 4.0
- 3.8: Naming Alkenes - CC BY-NC-SA 4.0
- 3.9: Naming Alkynes - CC BY-NC-SA 4.0
- 3.10: Alkenes and Alkynes - CC BY 4.0
- 3.11: Halogens - CC BY 4.0
- 3.12: Naming Alcohols and Phenols - CC BY-NC-SA 4.0
- 3.13: Alcohols - CC BY 4.0
- 3.14: Properties of Alkanes - CC BY-NC-SA 4.0
- 3.15: Chemistry Matters—Gasoline - CC BY-NC-SA 4.0
- 3.16: Key Terms - CC BY-NC-SA 4.0
- 3.17: Summary - Undeclared
- 3.18: Additional Problems - CC BY-NC-SA 4.0
- 3.19: Summary - CC BY-NC-SA 4.0
- 4: Organic Compounds - Cycloalkanes and their Stereochemistry -
CC BY-NC-SA 4.0
- 4.1: Why This Chapter? - CC BY-NC-SA 4.0
- 4.2: Conformations of Ethane - CC BY-NC-SA 4.0
- 4.3: Conformations of Other Alkanes - CC BY-NC-SA 4.0
- 4.4: Cis-Trans Isomerism in Cycloalkanes - CC BY-NC-SA 4.0
- 4.5: Stability of Cycloalkanes - Ring Strain - CC BY-NC-SA 4.0
- 4.6: Conformations of Cycloalkanes - CC BY-NC-SA 4.0
- 4.7: Conformations of Cyclohexane - CC BY-NC-SA 4.0
- 4.8: Axial and Equatorial Bonds in Cyclohexane - CC BY-NC-SA 4.0
- 4.9: Conformations of Monosubstituted Cyclohexanes - CC BY-NC-SA 4.0
- 4.10: Conformations of Disubstituted Cyclohexanes - CC BY-NC-SA 4.0
- 4.11: Conformations of Polycyclic Molecules - CC BY-NC-SA 4.0
- 4.12: Chemistry Matters—Molecular Mechanics - CC BY-NC-SA 4.0
- 4.13: Summary - Undeclared
- 4.14: Additional Problems - CC BY-NC-SA 4.0
- 5: Stereochemistry at Tetrahedral Centers -
CC BY-NC-SA 4.0
- 5.1: Why This Chapter? - CC BY-NC-SA 4.0
- 5.2: Enantiomers and the Tetrahedral Carbon - CC BY-NC-SA 4.0
- 5.3: The Reason for Handedness in Molecules - Chirality - CC BY-NC-SA 4.0
- 5.4: Optical Activity - CC BY-NC-SA 4.0
- 5.5: Pasteur's Discovery of Enantiomers - CC BY-NC-SA 4.0
- 5.6: Sequence Rules for Specifying Configuration - CC BY-NC-SA 4.0
- 5.7: Diastereomers - CC BY-NC-SA 4.0
- 5.8: Meso Compounds - CC BY-NC-SA 4.0
- 5.9: Racemic Mixtures and the Resolution of Enantiomers - CC BY-NC-SA 4.0
- 5.10: A Review of Isomerism - CC BY-NC-SA 4.0
- 5.11: Chirality at Nitrogen, Phosphorus, and Sulfur - CC BY-NC-SA 4.0
- 5.12: Prochirality - CC BY-NC-SA 4.0
- 5.13: Chirality in Nature and Chiral Environments - CC BY-NC-SA 4.0
- 5.14: Chemistry Matters—Chiral Drugs - CC BY-NC-SA 4.0
- 5.15: Stereochemistry at Tetrahedral Centers (Summary) - Undeclared
- 5.16: Additional Problems - CC BY-NC-SA 4.0
- 6: An Overview of Organic Reactions -
CC BY-NC-SA 4.0
- 6.1: Why This Chapter? - CC BY-NC-SA 4.0
- 6.2: Kinds of Organic Reactions - CC BY-NC-SA 4.0
- 6.3: How Organic Reactions Occur - Mechanisms - CC BY-NC-SA 4.0
- 6.4: Radical Reactions - CC BY-NC-SA 4.0
- 6.5: Polar Reactions - CC BY-NC-SA 4.0
- 6.6: An Example of a Polar Reaction - Addition of HBr to Ethylene - CC BY-NC-SA 4.0
- 6.7: Using Curved Arrows in Polar Reaction Mechanisms - CC BY-NC-SA 4.0
- 6.8: Describing a Reaction - Equilibria, Rates, and Energy Changes - CC BY-NC-SA 4.0
- 6.9: Describing a Reaction - Bond Dissociation Energies - CC BY-NC-SA 4.0
- 6.10: Describing a Reaction - Energy Diagrams and Transition States - CC BY-NC-SA 4.0
- 6.11: Describing a Reaction- Intermediates - CC BY-NC-SA 4.0
- 6.12: A Comparison between Biological Reactions and Laboratory Reactions - CC BY-NC-SA 4.0
- 6.13: Chemistry Matters—Where Do Drugs Come From? - CC BY-NC-SA 4.0
- 6.14: An Overview of Organic Reactions (Summary) - Undeclared
- 6.15: Additional Problems - CC BY-NC-SA 4.0
- 7: Alkenes- Structure and Reactivity -
CC BY-NC-SA 4.0
- 7.1: Why This Chapter? - CC BY-NC-SA 4.0
- 7.2: Industrial Preparation and Use of Alkenes - CC BY-NC-SA 4.0
- 7.3: Calculating Degree of Unsaturation - CC BY-NC-SA 4.0
- 7.4: Cis-Trans Isomerism in Alkenes - CC BY-NC-SA 4.0
- 7.5: Alkene Stereochemistry and the E,Z Designation - CC BY-NC-SA 4.0
- 7.6: Stability of Alkenes - CC BY-NC-SA 4.0
- 7.7: Electrophilic Addition Reactions of Alkenes - CC BY-NC-SA 4.0
- 7.8: Orientation of Electrophilic Additions - Markovnikov's Rule - CC BY-NC-SA 4.0
- 7.9: Carbocation Structure and Stability - CC BY-NC-SA 4.0
- 7.10: The Hammond Postulate - CC BY-NC-SA 4.0
- 7.11: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements - CC BY-NC-SA 4.0
- 7.12: Chemistry Matters—Bioprospecting- Hunting for Natural Products - CC BY-NC-SA 4.0
- 7.13: Alkenes - Structure and Reactivity (Summary) - Undeclared
- 7.14: Additional Problems - CC BY-NC-SA 4.0
- 8: Alkenes- Reactions and Synthesis -
CC BY-NC-SA 4.0
- 8.1: Why This Chapter? - CC BY-NC-SA 4.0
- 8.2: Preparation of Alkenes - A Preview of Elimination Reactions - CC BY-NC-SA 4.0
- 8.3: Halogenation of Alkenes - Addition of X₂ - CC BY-NC-SA 4.0
- 8.4: Halohydrins from Alkenes - Addition of HO-X - CC BY-NC-SA 4.0
- 8.5: Hydration of Alkenes- Acid-Catalyzed Hydration - CC BY-NC-SA 4.0
- 8.6: Stereochemistry of Reactions - Addition of H₂O to an Achiral Alkene - CC BY-NC-SA 4.0
- 8.7: Stereochemistry of Reactions - Addition of H₂O to a Chiral Alkene - CC BY-NC-SA 4.0
- 8.8: Hydration of Alkenes - Addition of H₂O by Oxymercuration - CC BY-NC-SA 4.0
- 8.9: Hydration of Alkenes - Addition of H₂O by Hydroboration - CC BY-NC-SA 4.0
- 8.10: Reduction of Alkenes - Hydrogenation - CC BY-NC-SA 4.0
- 8.11: Oxidation of Alkenes - Epoxidation and Hydroxylation - CC BY-NC-SA 4.0
- 8.12: Oxidation of Alkenes - Cleavage to Carbonyl Compounds - CC BY-NC-SA 4.0
- 8.13: Addition of Carbenes to Alkenes - Cyclopropane Synthesis - CC BY-NC-SA 4.0
- 8.14: Radical Additions to Alkenes - Chain-Growth Polymers - CC BY-NC-SA 4.0
- 8.15: Biological Additions of Radicals to Alkenes - CC BY-NC-SA 4.0
- 8.16: Chemistry Matters—Terpenes- Naturally Occurring Alkenes - CC BY-NC-SA 4.0
- 8.17: Alkenes - Reactions and Synthesis (Summary) - Undeclared
- 8.18: Additional Problems - CC BY-NC-SA 4.0
- 9: Alkynes - An Introduction to Organic Synthesis -
CC BY-NC-SA 4.0
- 9.1: Why This Chapter? - CC BY-NC-SA 4.0
- 9.2: Preparation of Alkynes - Elimination Reactions of Dihalides - CC BY-NC-SA 4.0
- 9.3: Reactions of Alkynes - Addition of HX and X₂ - CC BY-NC-SA 4.0
- 9.4: Hydration of Alkynes - CC BY-NC-SA 4.0
- 9.5: Reduction of Alkynes - CC BY-NC-SA 4.0
- 9.6: Oxidative Cleavage of Alkynes - CC BY-NC-SA 4.0
- 9.7: Alkyne Acidity - Formation of Acetylide Anions - CC BY-NC-SA 4.0
- 9.8: Alkylation of Acetylide Anions - CC BY-NC-SA 4.0
- 9.9: An Introduction to Organic Synthesis - CC BY-NC-SA 4.0
- 9.10: Chemistry Matters—The Art of Organic Synthesis - CC BY-NC-SA 4.0
- 9.11: Alkynes - An Introduction to Organic Synthesis (Summary) - Undeclared
- 9.12: Additional Problems - CC BY-NC-SA 4.0
- 10: Organohalides -
CC BY-NC-SA 4.0
- 10.1: Why This Chapter? - CC BY-NC-SA 4.0
- 10.2: Names and Properties of Alkyl Halides - CC BY-NC-SA 4.0
- 10.3: Preparing Alkyl Halides from Alkanes - Radical Halogenation - CC BY-NC-SA 4.0
- 10.4: Preparing Alkyl Halides from Alkenes - Allylic Bromination - CC BY-SA 4.0
- 10.5: Stability of the Allyl Radical - Resonance Revisited - CC BY-NC-SA 4.0
- 10.6: Radical Hydrobromination of Alkenes - HBr with peroxides - Undeclared
- 10.7: Preparing Alkyl Halides from Alcohols - CC BY-NC-SA 4.0
- 10.8: Reactions of Alkyl Halides - Grignard Reagents - CC BY-NC-SA 4.0
- 10.9: Organometallic Coupling Reactions - CC BY-NC-SA 4.0
- 10.10: Oxidation and Reduction in Organic Chemistry - CC BY-NC-SA 4.0
- 10.11: Chemistry Matters—Naturally Occurring Organohalides - CC BY-NC-SA 4.0
- 10.12: Organohalides (Summary) - Undeclared
- 10.13: Additional Problems - CC BY-NC-SA 4.0
- 11: Reactions of Alkyl Halides- Nucleophilic Substitutions and Eliminations -
CC BY-NC-SA 4.0
- 11.1: Why This Chapter? - CC BY-NC-SA 4.0
- 11.2: The Discovery of Nucleophilic Substitution Reactions - CC BY-NC-SA 4.0
- 11.3: The SN2 Reaction - CC BY-NC-SA 4.0
- 11.4: Characteristics of the SN2 Reaction - CC BY-NC-SA 4.0
- 11.5: The SN1 Reaction - CC BY-NC-SA 4.0
- 11.6: Characteristics of the SN1 Reaction - CC BY-NC-SA 4.0
- 11.7: Biological Substitution Reactions - CC BY-NC-SA 4.0
- 11.8: Elimination Reactions- Zaitsev's Rule - CC BY-NC-SA 4.0
- 11.9: The E2 Reaction and the Deuterium Isotope Effect - CC BY-NC-SA 4.0
- 11.10: The E2 Reaction and Cyclohexane Conformation - CC BY-NC-SA 4.0
- 11.11: The E1 and E1cB Reactions - CC BY-NC-SA 4.0
- 11.12: Biological Elimination Reactions - CC BY-NC-SA 4.0
- 11.13: A Summary of Reactivity - SN1, SN2, E1, E1cB, and E2 - CC BY-NC-SA 4.0
- 11.14: Chemistry Matters—Green Chemistry - CC BY-NC-SA 4.0
- 11.15: Reactions of Alkyl Halides - Nucleophilic Substitutions and Eliminations (Summary) - Undeclared
- 11.16: Additional Problems - CC BY-NC-SA 4.0
- 12: Alcohols and Phenols -
CC BY-NC-SA 4.0
- 12.1: Why This Chapter? - CC BY-NC-SA 4.0
- 12.2: Properties of Alcohols and Phenols - CC BY-NC-SA 4.0
- 12.3: Preparation of Alcohols- A Review - CC BY-NC-SA 4.0
- 12.4: Alcohols from Carbonyl Compounds- Reduction - CC BY-NC-SA 4.0
- 12.5: Alcohols from Carbonyl Compounds - Grignard Reagents - CC BY-NC-SA 4.0
- 12.6: Reactions of Alcohols - CC BY-NC-SA 4.0
- 12.7: Oxidation of Alcohols - CC BY-NC-SA 4.0
- 12.8: Protection of Alcohols - CC BY-NC-SA 4.0
- 12.9: Phenols and Their Uses - CC BY-SA 4.0
- 12.10: Reactions of Phenols - CC BY-SA 4.0
- 12.11: Chemistry Matters—Ethanol- Chemical, Drug, and Poison - CC BY-NC-SA 4.0
- 12.12: Additional Problems - CC BY-NC-SA 4.0
- 13: Structure Determination - Mass Spectrometry and Infrared Spectroscopy -
CC BY-NC-SA 4.0
- 13.1: Why This Chapter? - CC BY-NC-SA 4.0
- 13.2: Mass Spectrometry of Small Molecules - Magnetic-Sector Instruments - CC BY-NC-SA 4.0
- 13.3: Interpreting Mass Spectra - CC BY-NC-SA 4.0
- 13.4: Mass Spectroscopy and Natural Abundances of Isotopes - CC BY-NC-SA 4.0
- 13.5: Mass Spectrometry of Some Common Functional Groups - CC BY-NC-SA 4.0
- 13.6: Mass Spectrometry in Biological - Time-of-flight (TOF) Instruments - CC BY-NC-SA 4.0
- 13.7: Spectroscopy and the Electromagnetic Spectrum - CC BY-NC-SA 4.0
- 13.8: Infrared Spectroscopy - CC BY-NC-SA 4.0
- 13.9: Interpreting Infrared Spectra - CC BY-NC-SA 4.0
- 13.10: Infrared Spectra of Some Common Functional Groups - CC BY-NC-SA 4.0
- 13.11: Spectroscopy of Alcohols and Phenols - CC BY-NC-SA 4.0
- 13.12: Chemistry Matters—X-Ray Crystallography - CC BY-NC-SA 4.0
- 13.13: Structure Determination - Mass Spectrometry and Infrared Spectroscopy (Summary) - Undeclared
- 13.14: Mass Spectrometry Problems - Undeclared
- 13.15: Infrared Spectroscopy Problems - Undeclared
- 13.16: Additional Problems - CC BY-NC-SA 4.0
- 14: Structure Determination - Nuclear Magnetic Resonance Spectroscopy -
CC BY-NC-SA 4.0
- 14.1: Why This Chapter? - CC BY-NC-SA 4.0
- 14.2: Nuclear Magnetic Resonance Spectroscopy - CC BY-NC-SA 4.0
- 14.3: Acquiring a NMR Spectrum - CC BY-NC-SA 4.0
- 14.4: The Shielding Effect - CC BY-NC-SA 4.0
- 14.5: Proton Equivalence - CC BY-NC-SA 4.0
- 14.6: Chemical Shifts in ¹H NMR Spectroscopy - CC BY-NC-SA 4.0
- 14.7: ¹H NMR Signal Integration and Splitting - CC BY-NC-SA 4.0
- 14.8: More Complex Spin-Spin Splitting Patterns - CC BY-NC-SA 4.0
- 14.9: Uses of ¹H NMR Spectroscopy - CC BY-NC-SA 4.0
- 14.10: ¹³C NMR Spectroscopy - Signal Averaging and FT-NMR - CC BY-NC-SA 4.0
- 14.11: Characteristics of ¹³C NMR Spectroscopy - CC BY-NC-SA 4.0
- 14.12: DEPT ¹³C NMR Spectroscopy - CC BY-NC-SA 4.0
- 14.13: Uses of ¹³C NMR Spectroscopy - CC BY-NC-SA 4.0
- 14.14: Constructing Partial Structures in NMR Spectroscopy and Combined Structure Determination - CC BY-NC 4.0
- 14.15: Spectroscopy of Alcohols and Phenols - CC BY-NC-SA 4.0
- 14.16: Chemistry Matters—Magnetic Resonance Imaging (MRI) - CC BY-NC-SA 4.0
- 14.17: Structure Determination - Nuclear Magnetic Resonance Spectroscopy (Summary) - Undeclared
- 14.18: Proton NMR problems - Undeclared
- 14.19: Structure Determination Problems with C-13 NMR and 1-H NMR - Undeclared
- 14.20: Additional Problems - CC BY-NC-SA 4.0
- 15: Appendix -
CC BY-NC-SA 4.0
- 15.1: Appendix A - Nomenclature of Polyfunctional Organic Compounds - CC BY-NC-SA 4.0
- 15.2: Appendix B - Acidity Constants for Some Organic Compounds - CC BY-NC-SA 4.0
- 15.3: Appendix C - Glossary - CC BY-NC-SA 4.0
- 15.4: Appendix D - Periodic Table - CC BY-NC-SA 4.0
- 15.5: Answer Key -
CC BY-NC-SA 4.0
- 15.5.1: Chapter 1 - CC BY-NC-SA 4.0
- 15.5.2: Chapter 2 - CC BY-NC-SA 4.0
- 15.5.3: Chapter 3 - CC BY-NC-SA 4.0
- 15.5.4: Chapter 4 - CC BY-NC-SA 4.0
- 15.5.5: Chapter 5 - CC BY-NC-SA 4.0
- 15.5.6: Chapter 6 - CC BY-NC-SA 4.0
- 15.5.7: Chapter 7 - CC BY-NC-SA 4.0
- 15.5.8: Chapter 8 - CC BY-NC-SA 4.0
- 15.5.9: Chapter 9 - CC BY-NC-SA 4.0
- 15.5.10: Chapter 10 - CC BY-NC-SA 4.0
- 15.5.11: Chapter 11 - CC BY-NC-SA 4.0
- 15.5.12: Chapter 17 - CC BY-NC-SA 4.0
- 15.5.13: Chapter 12 - CC BY-NC-SA 4.0
- 15.5.14: Chapter 13 - CC BY-NC-SA 4.0
- Back Matter - Undeclared