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CHEM 231: Organic Chemistry I Textbook

This text is designed for CHEM 231 Organic Chemistry I, the first semester of a one-year organic chemistry sequence. Topics include the chemistry of hydrocarbons with emphasis on structure and reactivity of alkanes, alkenes, alkynes, alkyl halides, and conjugated systems. Mechanisms, stereochemistry and spectroscopy are an integral part of the course.

Chemistry

Author: Sol Parajon Puenzo
Publisher: Cañada College
Source: LibreTexts
License: CC BY-SA
Language: EN
Category: Basic Sciences

Read online Download PDF (open licence)

Contents· 254 sections

01: Structure and Bonding
1.01: Why This Chapter
1.02: Atomic Structure - The Nucleus
1.03: Atomic Structure - Orbitals
1.04: Atomic Structure - Electron Configurations
1.05: Development of Chemical Bonding Theory
1.06: Describing Chemical Bonds - Valence Bond Theory
1.07: sp Hybrid Orbitals and the Structure of Methane
1.08: sp Hybrid Orbitals and the Structure of Ethane
1.09: sp Hybrid Orbitals and the Structure of Ethylene
1.10: sp Hybrid Orbitals and the Structure of Acetylene
1.11: Hybridization of Nitrogen Oxygen Phosphorus and Sulfur
1.12: Describing Chemical Bonds - Molecular Orbital Theory
1.13: The Shapes of Molecules
1.14: Drawing Chemical Structures
1.15: Chemistry MattersOrganic Foods- Risk versus Benefit
1.16: Structure and Bonding (Summary)
1.17: Additional Problems
02: Polar Covalent Bonds Acids and Bases
2.01: Why This Chapter
2.02: Polar Covalent Bonds - Electronegativity
2.03: Polar Covalent Bonds - Dipole Moments
2.04: Intermolecular Forces
2.05: Physical Properties of Organic Compounds
2.06: Formal Charges
2.07: Resonance
2.08: Rules for Resonance Forms
2.09: Drawing Resonance Forms
2.10: Acids and Bases - The Brnsted-Lowry Definition
2.11: Acid and Base Strength
2.12: Predicting Acid-Base Reactions from pKa Values
2.13: Structural Effects on Acidity and Basicity
2.14: Organic Acids and Organic Bases
2.15: Acids and Bases - The Lewis Definition
2.16: Chemistry MattersAlkaloids- From Cocaine to Dental Anesthetics
2.17: Polar Covalent Bonds Acids and Bases (Summary)
2.18: Additional Problems
03: Organic Compounds- Functional Groups and Nomenclature
3.01: Why This Chapter
3.02: Functional Groups
3.03: Alkanes and Alkane Isomers
3.04: Alkyl Groups
3.05: Naming Alkanes
3.06: Naming Cycloalkanes
3.07: Alkyl Substituents
3.08: Naming Alkenes
3.09: Naming Alkynes
3.10: Alkenes and Alkynes
3.11: Halogens
3.12: Naming Alcohols and Phenols
3.13: Alcohols
3.14: Properties of Alkanes
3.15: Chemistry MattersGasoline
3.16: Key Terms
3.17: Summary
3.18: Additional Problems
3.19: Summary
04: Organic Compounds - Cycloalkanes and their Stereochemistry
4.01: Why This Chapter
4.02: Conformations of Ethane
4.03: Conformations of Other Alkanes
4.04: Cis-Trans Isomerism in Cycloalkanes
4.05: Stability of Cycloalkanes - Ring Strain
4.06: Conformations of Cycloalkanes
4.07: Conformations of Cyclohexane
4.08: Axial and Equatorial Bonds in Cyclohexane
4.09: Conformations of Monosubstituted Cyclohexanes
4.10: Conformations of Disubstituted Cyclohexanes
4.11: Conformations of Polycyclic Molecules
4.12: Chemistry MattersMolecular Mechanics
4.13: Summary
4.14: Additional Problems
05: Stereochemistry at Tetrahedral Centers
5.01: Why This Chapter
5.02: Enantiomers and the Tetrahedral Carbon
5.03: The Reason for Handedness in Molecules - Chirality
5.04: Optical Activity
5.05: Pasteur's Discovery of Enantiomers
5.06: Sequence Rules for Specifying Configuration
5.07: Diastereomers
5.08: Meso Compounds
5.09: Racemic Mixtures and the Resolution of Enantiomers
5.10: A Review of Isomerism
5.11: Chirality at Nitrogen Phosphorus and Sulfur
5.12: Prochirality
5.13: Chirality in Nature and Chiral Environments
5.14: Chemistry MattersChiral Drugs
5.15: Stereochemistry at Tetrahedral Centers (Summary)
5.16: Additional Problems
06: An Overview of Organic Reactions
6.01: Why This Chapter
6.02: Kinds of Organic Reactions
6.03: How Organic Reactions Occur - Mechanisms
6.04: Radical Reactions
6.05: Polar Reactions
6.06: An Example of a Polar Reaction - Addition of HBr to Ethylene
6.07: Using Curved Arrows in Polar Reaction Mechanisms
6.08: Describing a Reaction - Equilibria Rates and Energy Changes
6.09: Describing a Reaction - Bond Dissociation Energies
6.10: Describing a Reaction - Energy Diagrams and Transition States
6.11: Describing a Reaction- Intermediates
6.12: A Comparison between Biological Reactions and Laboratory Reactions
6.13: Chemistry MattersWhere Do Drugs Come From
6.14: An Overview of Organic Reactions (Summary)
6.15: Additional Problems
07: Alkenes- Structure and Reactivity
7.01: Why This Chapter
7.02: Industrial Preparation and Use of Alkenes
7.03: Calculating Degree of Unsaturation
7.04: Cis-Trans Isomerism in Alkenes
7.05: Alkene Stereochemistry and the EZ Designation
7.06: Stability of Alkenes
7.07: Electrophilic Addition Reactions of Alkenes
7.08: Orientation of Electrophilic Additions - Markovnikov's Rule
7.09: Carbocation Structure and Stability
7.10: The Hammond Postulate
7.11: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements
7.12: Chemistry MattersBioprospecting- Hunting for Natural Products
7.13: Alkenes - Structure and Reactivity (Summary)
7.14: Additional Problems
08: Alkenes- Reactions and Synthesis
8.01: Why This Chapter
8.02: Preparation of Alkenes - A Preview of Elimination Reactions
8.03: Halogenation of Alkenes - Addition of X
8.04: Halohydrins from Alkenes - Addition of HO-X
8.05: Hydration of Alkenes- Acid-Catalyzed Hydration
8.06: Stereochemistry of Reactions - Addition of HO to an Achiral Alkene
8.07: Stereochemistry of Reactions - Addition of HO to a Chiral Alkene
8.08: Hydration of Alkenes - Addition of HO by Oxymercuration
8.09: Hydration of Alkenes - Addition of HO by Hydroboration
8.10: Reduction of Alkenes - Hydrogenation
8.11: Oxidation of Alkenes - Epoxidation and Hydroxylation
8.12: Oxidation of Alkenes - Cleavage to Carbonyl Compounds
8.13: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
8.14: Radical Additions to Alkenes - Chain-Growth Polymers
8.15: Biological Additions of Radicals to Alkenes
8.16: Chemistry MattersTerpenes- Naturally Occurring Alkenes
8.17: Alkenes - Reactions and Synthesis (Summary)
8.18: Additional Problems
09: Alkynes - An Introduction to Organic Synthesis
9.01: Why This Chapter
9.02: Preparation of Alkynes - Elimination Reactions of Dihalides
9.03: Reactions of Alkynes - Addition of HX and X
9.04: Hydration of Alkynes
9.05: Reduction of Alkynes
9.06: Oxidative Cleavage of Alkynes
9.07: Alkyne Acidity - Formation of Acetylide Anions
9.08: Alkylation of Acetylide Anions
9.09: An Introduction to Organic Synthesis
9.10: Chemistry MattersThe Art of Organic Synthesis
9.11: Alkynes - An Introduction to Organic Synthesis (Summary)
9.12: Additional Problems
10: Organohalides
10.01: Why This Chapter
10.02: Names and Properties of Alkyl Halides
10.03: Preparing Alkyl Halides from Alkanes - Radical Halogenation
10.04: Preparing Alkyl Halides from Alkenes - Allylic Bromination
10.05: Stability of the Allyl Radical - Resonance Revisited
10.06: Radical Hydrobromination of Alkenes - HBr with peroxides
10.07: Preparing Alkyl Halides from Alcohols
10.08: Reactions of Alkyl Halides - Grignard Reagents
10.09: Organometallic Coupling Reactions
10.10: Oxidation and Reduction in Organic Chemistry
10.11: Chemistry MattersNaturally Occurring Organohalides
10.12: Organohalides (Summary)
10.13: Additional Problems
11: Reactions of Alkyl Halides- Nucleophilic Substitutions and Eliminations
11.01: Why This Chapter
11.02: The Discovery of Nucleophilic Substitution Reactions
11.03: The SN2 Reaction
11.04: Characteristics of the SN2 Reaction
11.05: The SN1 Reaction
11.06: Characteristics of the SN1 Reaction
11.07: Biological Substitution Reactions
11.08: Elimination Reactions- Zaitsev's Rule
11.09: The E2 Reaction and the Deuterium Isotope Effect
11.10: The E2 Reaction and Cyclohexane Conformation
11.11: The E1 and E1cB Reactions
11.12: Biological Elimination Reactions
11.13: A Summary of Reactivity - SN1 SN2 E1 E1cB and E2
11.14: Chemistry MattersGreen Chemistry
11.15: Reactions of Alkyl Halides - Nucleophilic Substitutions and Eliminations (Summary)
11.16: Additional Problems
12: Alcohols and Phenols
12.01: Why This Chapter
12.02: Properties of Alcohols and Phenols
12.03: Preparation of Alcohols- A Review
12.04: Alcohols from Carbonyl Compounds- Reduction
12.05: Alcohols from Carbonyl Compounds - Grignard Reagents
12.06: Reactions of Alcohols
12.07: Oxidation of Alcohols
12.08: Protection of Alcohols
12.09: Phenols and Their Uses
12.10: Reactions of Phenols
12.11: Chemistry MattersEthanol- Chemical Drug and Poison
12.12: Additional Problems
13: Structure Determination - Mass Spectrometry and Infrared Spectroscopy
13.01: Why This Chapter
13.02: Mass Spectrometry of Small Molecules - Magnetic-Sector Instruments
13.03: Interpreting Mass Spectra
13.04: Mass Spectroscopy and Natural Abundances of Isotopes
13.05: Mass Spectrometry of Some Common Functional Groups
13.06: Mass Spectrometry in Biological - Time-of-flight (TOF) Instruments
13.07: Spectroscopy and the Electromagnetic Spectrum
13.08: Infrared Spectroscopy
13.09: Interpreting Infrared Spectra
13.10: Infrared Spectra of Some Common Functional Groups
13.11: Spectroscopy of Alcohols and Phenols
13.12: Chemistry MattersX-Ray Crystallography
13.13: Structure Determination - Mass Spectrometry and Infrared Spectroscopy (Summary)
13.14: Mass Spectrometry Problems
13.15: Infrared Spectroscopy Problems
13.16: Additional Problems
14: Structure Determination - Nuclear Magnetic Resonance Spectroscopy
14.01: Why This Chapter
14.02: Nuclear Magnetic Resonance Spectroscopy
14.03: Acquiring a NMR Spectrum
14.04: The Shielding Effect
14.05: Proton Equivalence
14.06: Chemical Shifts in H NMR Spectroscopy
14.07: H NMR Signal Integration and Splitting
14.08: More Complex Spin-Spin Splitting Patterns
14.09: Uses of H NMR Spectroscopy
14.10: C NMR Spectroscopy - Signal Averaging and FT-NMR
14.11: Characteristics of C NMR Spectroscopy
14.12: DEPT C NMR Spectroscopy
14.13: Uses of C NMR Spectroscopy
14.14: Constructing Partial Structures in NMR Spectroscopy and Combined Structure Determination
14.15: Spectroscopy of Alcohols and Phenols
14.16: Chemistry MattersMagnetic Resonance Imaging (MRI)
14.17: Structure Determination - Nuclear Magnetic Resonance Spectroscopy (Summary)
14.18: Proton NMR problems
14.19: Structure Determination Problems with C-13 NMR and 1-H NMR
14.20: Additional Problems
15: Appendix
15.01: Appendix A - Nomenclature of Polyfunctional Organic Compounds
15.02: Appendix B - Acidity Constants for Some Organic Compounds
15.03: Appendix C - Glossary
15.04: Appendix D - Periodic Table
15.05: Answer Key
15.5.01: Chapter 1
15.5.02: Chapter 2
15.5.03: Chapter 3
15.5.04: Chapter 4
15.5.05: Chapter 5
15.5.06: Chapter 6
15.5.07: Chapter 7
15.5.08: Chapter 8
15.5.09: Chapter 9
15.5.10: Chapter 10
15.5.11: Chapter 11
15.5.12: Chapter 17
15.5.13: Chapter 12
15.5.14: Chapter 13