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Organic Chemistry I

Welcome to organic chemistry! This covers first semester materials up to IR and NMR analysis. The book is about 740 pages long and can be printed at the LibreTexts online bookstore

Organic Chemistry Chemistry

Author: Wade Textmap
Publisher: LibreTexts
Source: LibreTexts
Language: EN
Category: Basic Sciences

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Contents· 198 sections

01: Introduction and Review
1.01: The Origins of Organic Chemistry
1.02: Principles of Atomic Structure (Review)
1.03: Electronic Structure (Review)
1.04: Electron Configurations and Electronic Orbital Diagrams (Review)
1.05: Octet Rule - Ionic and Covalent Bonding (Review)
1.06: Lewis Structures and Formal Charges (Review)
1.07: Common Bonding Patterns for Organic Chemistry
1.08: Structural Formulas - Lewis Kekule Bond-line Condensed and Perspective
1.09: Electronegativity and Bond Polarity (Review)
1.10: Resonance
1.11: Arrhenius Acids and Bases (Review)
1.12: Lewis Acids and Bases
1.13: Distinguishing between pH and pKa
1.14: Predicting Relative Acidity
1.15: Molecular Formulas and Empirical Formulas (Review)
1.16: Additional Exercises
1.17: Solutions to Additional Exercises
1.18: Brnsted-Lowry Acids and Bases (Review)
02: Structure and Properties of Organic Molecules
2.01: Pearls of Wisdom
2.02: Molecular Orbital (MO) Theory (Review)
2.03: Hybridization and Molecular Shapes (Review)
2.04: 2.4 Conjugated Pi Bond Systems
2.05: Lone Pair Electrons and Bonding Theories
2.06: Bond Rotation
2.07: Isomerism Introduction
2.08: Hydrocarbons and the Homologous Series
2.09: Organic Functional Groups
2.10: Intermolecular Forces (IMFs) - Review
2.11: Intermolecular Forces and Relative Boiling Points (bp)
2.12: Intermolecular Forces and Solubilities
2.13: Additional Practice Problems
2.14: Organic Functional Groups- H-bond donors and H-bond acceptors
2.15: Solutions to Additional Exercises
2.16: Additional Exercises
03: Functional Groups and Nomenclature
3.01: Generic (Abbreviated) Structures (aka R Groups)
3.02: Overview of the IUPAC Naming Strategy
3.03: Alkanes
3.04: Cycloalkanes
3.05: Haloalkane - Classification and Nomenclature
3.06: Alkenes
3.07: Alkynes
3.08: 3.8 Alcohols - Classification and Nomenclature
3.09: Ethers Epoxides and Sulfides
3.10: Benzene and its Derivatives
3.11: Aldehydes and Ketones
3.12: Amines - Classification and Nomenclature
3.13: Carboxylic Acids
3.14: The Carboxylic Acid Derivatives
3.15: Additional Exercises
3.16: Solutions to Additional Exercises
3.17: Appendix - IUPAC Nomenclature Rules
04: Structure and Stereochemistry of Alkanes
4.01: Hydrocarbon Functional Groups
4.02: Physical Properties of Alkanes
4.03: Structure and Conformations of Alkanes
4.04: Conformations of Butane
4.05: Conformations of Higher Alkanes
4.06: Cycloalkanes and Ring Strain
4.07: Cyclohexane Conformations
4.08: Conformations of Monosubstituted Cyclohexanes
4.09: Cis-trans Isomerism in Cycloalkanes
4.10: Conformations of Disubstituted Cyclohexanes
4.11: Joined Rings
4.12: Uses and Sources of Alkanes
4.13: Reactions of Alkanes - a Brief Overview
4.14: Additional Exercises
4.15: Solutions to Additional Exercises
05: An Introduction to Organic Reactions using Free Radical Halogenation of Alkanes
5.01: Types of Organic Reactions
5.02: Reaction Mechanism Notation and Symbols
5.03: Polar Reactions- the Dance of the Nucleophile and Electrophile
5.04: Describing a Reaction - Equilibrium and Free Energy Changes
5.05: Homolytic Cleavage and Bond Dissociation Energies
5.06: Reaction Energy Diagrams and Transition States
5.07: Reactive Intermediates - Carbocations
5.08: Reactive Intermediates - Radicals
5.09: Reactive Intermediates- Carbanions and Carbon Acids
5.10: The Free-Radical Halogenation of Alkanes
5.11: Reactivity and Selectivity
5.12: A Comparison between Biological Reactions and Laboratory Reactions
5.13: Additional Exercises
5.14: Solutions to Additional Exercises
06: Stereochemistry at Tetrahedral Centers
6.01: Chirality
6.02: Fischer Projections to communicate Chirality
6.03: Absolute Configuration and the (R) and (S) System
6.04: Diastereomers - more than one chiral center
6.05: Meso Compounds
6.06: Isomerism Summary Diagram
6.07: Optical Activity and Racemic Mixtures
6.08: Resolution (Separation) of Enantiomers
6.09: Stereochemistry of Molecules with Three or More Asymmetric Carbons
6.10: Absolute and Relative Configuration - the distinction
6.11: Chirality at Nitrogen Phosphorus and Sulfur
6.12: Biochemistry of Enantiomers
6.13: The Discovery of Enantiomers
6.14: Additional Exercises
6.15: Solutions to Additional Exercises
07: Alkyl Halides- Nucleophilic Substitution and Elimination
7.01: Alkyl Halides - Structure and Physical Properties
7.02: Common Uses of Alkyl Halides
7.03: Preparation of Alkyl Halides
7.04: Reactions of Alkyl Halides- Substitution and Elimination
7.05: The S2 Reaction
7.06: Characteristics of the S2 Reaction
7.07: Stereochemistry of the SN2 Reaction
7.08: The S1 Reaction
7.09: Characteristics of the S1 Reaction
7.10: Rearrangements of the Carbocation and S1 Reactions
7.11: The Hammond Postulate and Transition States
7.12: Comparison of SN1 and SN2 Reactions
7.13: Characteristics of the E2 Reaction
7.14: Zaitsev's Rule
7.15: Characteristics of the E1 Reaction
7.16: E2 Regiochemistry and Cyclohexane Conformations
7.17: The E2 Reaction and the Deuterium Isotope Effect
7.18: Comparison of E1 and E2 Reactions
7.19: Comparing Substitution and Elimination Reactions
7.20: Biological Substitution Reactions
7.21: Biological Elimination Reactions
7.22: Additional Exercises
7.23: Solutions to Additional Exercises
08: Structure and Synthesis of Alkenes
8.01: Alkene Structure
8.02: Physical Properties and Important Common Names
8.03: The Alkene Double Bond and Stereoisomerism
8.04: Degrees of Unsaturation
8.05: The E Z System (when cis trans does not work)
8.06: Stability of Alkenes
8.07: Alkene Synthesis by Elimination of Alkyl Halides
8.08: Alkene Synthesis by Dehydration of Alcohols
8.09: Uses and Sources of Alkenes
8.10: Additional Exercises
8.11: Solutions to Additional Exercises
09: Reactions of Alkenes
9.01: Electrophilic Addition Reactions (EARs)
9.02: Addition of Hydrogen Halides to Symmetrical Alkenes
9.03: Alkene Asymmetry and Markovnikov's Rule
9.04: Hydration- Acid Catalyzed Addition of Water
9.05: Hydration- Oxymercuration-Demercuration
9.06: Hydration - Hydroboration-Oxidation
9.07: Stereochemistry of Reactions - Hydration of Achiral Alkenes
9.08: Stereochemistry of Reactions - Hydration of Chiral Alkenes
9.09: Addition of Halogens
9.10: Formation of Halohydrins
9.11: Reduction of Alkenes - Catalytic Hydrogenation
9.12: Oxidation of Alkenes - Epoxidation
9.13: Dihydroxylation of Alkenes
9.14: Opening of Epoxides - Acidic versus Basic Conditions
9.15: Oxidative Cleavage of Alkenes
9.16: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
9.17: Radical Chain-Growth Polymerization
9.18: Biological Additions of Radicals to Alkenes
9.19: Additional Exercises
9.20: Solutions to Additional Exercises
10: Alkynes
10.01: Structure and Physical Properties
10.02: 10.2 Synthesis of Alkynes - Elimination Reactions of Dihalides
10.03: Reactions of Alkynes - Addition of HX and X
10.04: Hydration of Alkynes for Markovnikov Products
10.05: Hydration of Alkynes for Anti-Markovnikov Products
10.06: 10.6 Reduction of Alkynes
10.07: Oxidation of Alkynes
10.08: Acidity of Terminal Alkynes and Acetylide Ions
10.09: Synthesis of Larger Alkynes from Acetylides
10.10: An Introduction to Multiple Step Synthesis
10.11: Additional Exercises
10.12: Solutions to Additional Exercises
11: Infrared Spectroscopy and Mass Spectrometry
11.01: The Electromagnetic Spectrum and Spectroscopy
11.02: Infrared (IR) Spectroscopy
11.03: IR-Active and IR-Inactive Vibrations
11.04: Interpretting IR Spectra
11.05: Infrared Spectra of Some Common Functional Groups
11.06: Summary and Tips to Distinguish between Carbonyl Functional Groups
11.07: Mass Spectrometry - an introduction
11.08: Fragmentation Patterns in Mass Spectrometry
11.09: Useful Patterns for Structure Elucidation
11.10: Determination of the Molecular Formula by High Resolution Mass Spectrometry
12: Nuclear Magnetic Resonance Spectroscopy
12.01: Theory of Nuclear Magnetic Resonance (NMR)
12.02: NMR Spectra - an introduction and overview
12.03: Chemical Shifts and Shielding
12.04: H NMR Spectroscopy and Proton Equivalence
12.05: Functional Groups and Chemical Shifts in H NMR Spectroscopy
12.06: Integration of H NMR Absorptions- Proton Counting
12.07: Spin-Spin Splitting in H NMR Spectra
12.08: More Complex Spin-Spin Splitting Patterns
12.09: Uses of H NMR Spectroscopy
12.10: C NMR Spectroscopy
12.11: Chemical Shifts and Interpreting C NMR Spectra
12.12: C NMR Spectroscopy and DEPT
12.13: Uses of C NMR Spectroscopy
12.14: More NMR Examples
12.15: Sample NMR Spectra