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Organic Chemistry

306 lessons · 1,546 glossary terms — Covers Structure and Bonding, Polar Covalent Bonds; Acids and Bases and Organic Compounds: Alkanes and Their Stereochemistry, and 28 more chapters.

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Structure and Bonding12 lessons

Chapter page

  1. Atomic Structure: The Nucleus
  2. Atomic Structure: Orbitals
  3. Atomic Structure: Electron Configurations
  4. Development of Chemical Bonding Theory
  5. Describing Chemical Bonds: Valence Bond Theory
  6. sp3 Hybrid Orbitals and the Structure of Methane
  7. sp3 Hybrid Orbitals and the Structure of Ethane
  8. sp2 Hybrid Orbitals and the Structure of Ethylene
  9. sp Hybrid Orbitals and the Structure of Acetylene
  10. Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur
  11. Describing Chemical Bonds: Molecular Orbital Theory
  12. Drawing Chemical Structures

Polar Covalent Bonds; Acids and Bases12 lessons

Chapter page

  1. Polar Covalent Bonds and Electronegativity
  2. Polar Covalent Bonds and Dipole Moments
  3. Formal Charges
  4. Resonance
  5. Rules for Resonance Forms
  6. Drawing Resonance Forms
  7. Acids and Bases: The Brønsted–Lowry Definition
  8. Acid and Base Strength
  9. Predicting Acid–Base Reactions from pKa Values
  10. Organic Acids and Organic Bases
  11. Acids and Bases: The Lewis Definition
  12. Noncovalent Interactions between Molecules

Organic Compounds: Alkanes and Their Stereochemistry7 lessons

Chapter page

  1. Functional Groups
  2. Alkanes and Alkane Isomers
  3. Alkyl Groups
  4. Naming Alkanes
  5. Properties of Alkanes
  6. Conformations of Ethane
  7. Conformations of Other Alkanes

Organic Compounds: Cycloalkanes and Their Stereochemistry9 lessons

Chapter page

  1. Naming Cycloalkanes
  2. Cis–Trans Isomerism in Cycloalkanes
  3. Stability of Cycloalkanes: Ring Strain
  4. Conformations of Cycloalkanes
  5. Conformations of Cyclohexane
  6. Axial and Equatorial Bonds in Cyclohexane
  7. Conformations of Monosubstituted Cyclohexanes
  8. Conformations of Disubstituted Cyclohexanes
  9. Conformations of Polycyclic Molecules

Stereochemistry at Tetrahedral Centers12 lessons

Chapter page

  1. Enantiomers and the Tetrahedral Carbon
  2. The Reason for Handedness in Molecules: Chirality
  3. Optical Activity
  4. Pasteur’s Discovery of Enantiomers
  5. Sequence Rules for Specifying Configuration
  6. Diastereomers
  7. Meso Compounds
  8. Racemic Mixtures and the Resolution of Enantiomers
  9. A Review of Isomerism
  10. Chirality at Nitrogen, Phosphorus, and Sulfur
  11. Prochirality
  12. Chirality in Nature and Chiral Environments

An Overview of Organic Reactions11 lessons

Chapter page

  1. Kinds of Organic Reactions
  2. How Organic Reactions Occur: Mechanisms
  3. Polar Reactions
  4. An Example of a Polar Reaction: Addition of HBr to Ethylene
  5. Using Curved Arrows in Polar Reaction Mechanisms
  6. Radical Reactions
  7. Describing a Reaction: Equilibria, Rates, and Energy Changes
  8. Describing a Reaction: Bond Dissociation Energies
  9. Describing a Reaction: Energy Diagrams and Transition States
  10. Describing a Reaction: Intermediates
  11. A Comparison Between Biological Reactions and Laboratory Reactions

Alkenes: Structure and Reactivity11 lessons

Chapter page

  1. Industrial Preparation and Use of Alkenes
  2. Calculating the Degree of Unsaturation
  3. Naming Alkenes
  4. Cis–Trans Isomerism in Alkenes
  5. Alkene Stereochemistry and the E,Z Designation
  6. Stability of Alkenes
  7. Electrophilic Addition Reactions of Alkenes
  8. Orientation of Electrophilic Additions: Markovnikov’s Rule
  9. Carbocation Structure and Stability
  10. The Hammond Postulate
  11. Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements

Alkenes: Reactions and Synthesis13 lessons

Chapter page

  1. Preparing Alkenes: A Preview of Elimination Reactions
  2. Halogenation of Alkenes: Addition of X2
  3. Halohydrins from Alkenes: Addition of HO-X
  4. Hydration of Alkenes: Addition of H2O by Oxymercuration
  5. Hydration of Alkenes: Addition of H2O by Hydroboration
  6. Reduction of Alkenes: Hydrogenation
  7. Oxidation of Alkenes: Epoxidation and Hydroxylation
  8. Oxidation of Alkenes: Cleavage to Carbonyl Compounds
  9. Addition of Carbenes to Alkenes: Cyclopropane Synthesis
  10. Radical Additions to Alkenes: Chain-Growth Polymers
  11. Biological Additions of Radicals to Alkenes
  12. Reaction Stereochemistry: Addition of H2O to an Achiral Alkene
  13. Reaction Stereochemistry: Addition of H2O to a Chiral Alkene

Alkynes: An Introduction to Organic Synthesis9 lessons

Chapter page

  1. Naming Alkynes
  2. Preparation of Alkynes: Elimination Reactions of Dihalides
  3. Reactions of Alkynes: Addition of HX and X2
  4. Hydration of Alkynes
  5. Reduction of Alkynes
  6. Oxidative Cleavage of Alkynes
  7. Alkyne Acidity: Formation of Acetylide Anions
  8. Alkylation of Acetylide Anions
  9. An Introduction to Organic Synthesis

Organohalides8 lessons

Chapter page

  1. Names and Structures of Alkyl Halides
  2. Preparing Alkyl Halides from Alkanes: Radical Halogenation
  3. Preparing Alkyl Halides from Alkenes: Allylic Bromination
  4. Stability of the Allyl Radical: Resonance Revisited
  5. Preparing Alkyl Halides from Alcohols
  6. Reactions of Alkyl Halides: Grignard Reagents
  7. Organometallic Coupling Reactions
  8. Oxidation and Reduction in Organic Chemistry

Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations12 lessons

Chapter page

  1. The Discovery of Nucleophilic Substitution Reactions
  2. The SN2 Reaction
  3. Characteristics of the SN2 Reaction
  4. The SN1 Reaction
  5. Characteristics of the SN1 Reaction
  6. Biological Substitution Reactions
  7. Elimination Reactions: Zaitsev’s Rule
  8. The E2 Reaction and the Deuterium Isotope Effect
  9. The E2 Reaction and Cyclohexane Conformation
  10. The E1 and E1cB Reactions
  11. Biological Elimination Reactions
  12. A Summary of Reactivity: SN1, SN2, E1, E1cB, and E2

Structure Determination: Mass Spectrometry and Infrared Spectroscopy8 lessons

Chapter page

  1. Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments
  2. Interpreting Mass Spectra
  3. Mass Spectrometry of Some Common Functional Groups
  4. Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments
  5. Spectroscopy and the Electromagnetic Spectrum
  6. Infrared Spectroscopy
  7. Interpreting Infrared Spectra
  8. Infrared Spectra of Some Common Functional Groups

Structure Determination: Nuclear Magnetic Resonance Spectroscopy13 lessons

Chapter page

  1. Nuclear Magnetic Resonance Spectroscopy
  2. The Nature of NMR Absorptions
  3. Chemical Shifts
  4. Chemical Shifts in 1H NMR Spectroscopy
  5. Integration of 1H NMR Absorptions: Proton Counting
  6. Spin–Spin Splitting in 1H NMR Spectra
  7. 1H NMR Spectroscopy and Proton Equivalence
  8. More Complex Spin–Spin Splitting Patterns
  9. Uses of 1H NMR Spectroscopy
  10. 13C NMR Spectroscopy: Signal Averaging and FT–NMR
  11. Characteristics of 13C NMR Spectroscopy
  12. DEPT 13C NMR Spectroscopy
  13. Uses of 13C NMR Spectroscopy

Conjugated Compounds and Ultraviolet Spectroscopy9 lessons

Chapter page

  1. Stability of Conjugated Dienes: Molecular Orbital Theory
  2. Electrophilic Additions to Conjugated Dienes: Allylic Carbocations
  3. Kinetic versus Thermodynamic Control of Reactions
  4. The Diels–Alder Cycloaddition Reaction
  5. Characteristics of the Diels–Alder Reaction
  6. Diene Polymers: Natural and Synthetic Rubbers
  7. Ultraviolet Spectroscopy
  8. Interpreting Ultraviolet Spectra: The Effect of Conjugation
  9. Conjugation, Color, and the Chemistry of Vision

Benzene and Aromaticity7 lessons

Chapter page

  1. Naming Aromatic Compounds
  2. Structure and Stability of Benzene
  3. Aromaticity and the Hückel 4n + 2 Rule
  4. Aromatic Ions
  5. Aromatic Heterocycles: Pyridine and Pyrrole
  6. Polycyclic Aromatic Compounds
  7. Spectroscopy of Aromatic Compounds

Chemistry of Benzene: Electrophilic Aromatic Substitution10 lessons

Chapter page

  1. Electrophilic Aromatic Substitution Reactions: Bromination
  2. Other Aromatic Substitutions
  3. Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction
  4. Substituent Effects in Electrophilic Substitutions
  5. Trisubstituted Benzenes: Additivity of Effects
  6. Nucleophilic Aromatic Substitution
  7. Benzyne
  8. Oxidation of Aromatic Compounds
  9. Reduction of Aromatic Compounds
  10. Synthesis of Polysubstituted Benzenes

Alcohols and Phenols11 lessons

Chapter page

  1. Naming Alcohols and Phenols
  2. Properties of Alcohols and Phenols
  3. Preparation of Alcohols: A Review
  4. Alcohols from Carbonyl Compounds: Reduction
  5. Alcohols from Carbonyl Compounds: Grignard Reaction
  6. Reactions of Alcohols
  7. Oxidation of Alcohols
  8. Protection of Alcohols
  9. Phenols and Their Uses
  10. Reactions of Phenols
  11. Spectroscopy of Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides8 lessons

Chapter page

  1. Names and Properties of Ethers
  2. Preparing Ethers
  3. Reactions of Ethers: Acidic Cleavage
  4. Cyclic Ethers: Epoxides
  5. Reactions of Epoxides: Ring-Opening
  6. Crown Ethers
  7. Thiols and Sulfides
  8. Spectroscopy of Ethers

Aldehydes and Ketones: Nucleophilic Addition Reactions14 lessons

Chapter page

  1. Naming Aldehydes and Ketones
  2. Preparing Aldehydes and Ketones
  3. Oxidation of Aldehydes and Ketones
  4. Nucleophilic Addition Reactions of Aldehydes and Ketones
  5. Nucleophilic Addition of H2O: Hydration
  6. Nucleophilic Addition of HCN: Cyanohydrin Formation
  7. Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation
  8. Nucleophilic Addition of Amines: Imine and Enamine Formation
  9. Nucleophilic Addition of Hydrazine: The Wolff–Kishner Reaction
  10. Nucleophilic Addition of Alcohols: Acetal Formation
  11. Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction
  12. Biological Reductions
  13. Conjugate Nucleophilic Addition to α,β‑Unsaturated Aldehydes and Ketones
  14. Spectroscopy of Aldehydes and Ketones

Carboxylic Acids and Nitriles8 lessons

Chapter page

  1. Naming Carboxylic Acids and Nitriles
  2. Structure and Properties of Carboxylic Acids
  3. Biological Acids and the Henderson–Hasselbalch Equation
  4. Substituent Effects on Acidity
  5. Preparing Carboxylic Acids
  6. Reactions of Carboxylic Acids: An Overview
  7. Chemistry of Nitriles
  8. Spectroscopy of Carboxylic Acids and Nitriles

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions10 lessons

Chapter page

  1. Naming Carboxylic Acid Derivatives
  2. Nucleophilic Acyl Substitution Reactions
  3. Reactions of Carboxylic Acids
  4. Chemistry of Acid Halides
  5. Chemistry of Acid Anhydrides
  6. Chemistry of Esters
  7. Chemistry of Amides
  8. Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives
  9. Polyamides and Polyesters: Step-Growth Polymers
  10. Spectroscopy of Carboxylic Acid Derivatives

Carbonyl Alpha-Substitution Reactions7 lessons

Chapter page

  1. Keto–Enol Tautomerism
  2. Reactivity of Enols: α-Substitution Reactions
  3. Alpha Halogenation of Aldehydes and Ketones
  4. Alpha Bromination of Carboxylic Acids
  5. Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation
  6. Reactivity of Enolate Ions
  7. Alkylation of Enolate Ions

Carbonyl Condensation Reactions13 lessons

Chapter page

  1. Carbonyl Condensations: The Aldol Reaction
  2. Carbonyl Condensations versus Alpha Substitutions
  3. Dehydration of Aldol Products: Synthesis of Enones
  4. Using Aldol Reactions in Synthesis
  5. Mixed Aldol Reactions
  6. Intramolecular Aldol Reactions
  7. The Claisen Condensation Reaction
  8. Mixed Claisen Condensations
  9. Intramolecular Claisen Condensations: The Dieckmann Cyclization
  10. Conjugate Carbonyl Additions: The Michael Reaction
  11. Carbonyl Condensations with Enamines: The Stork Enamine Reaction
  12. The Robinson Annulation Reaction
  13. Some Biological Carbonyl Condensation Reactions

Amines and Heterocycles10 lessons

Chapter page

  1. Naming Amines
  2. Structure and Properties of Amines
  3. Basicity of Amines
  4. Basicity of Arylamines
  5. Biological Amines and the Henderson–Hasselbalch Equation
  6. Synthesis of Amines
  7. Reactions of Amines
  8. Reactions of Arylamines
  9. Heterocyclic Amines
  10. Spectroscopy of Amines

Biomolecules: Carbohydrates10 lessons

Chapter page

  1. Classification of Carbohydrates
  2. Representing Carbohydrate Stereochemistry: Fischer Projections
  3. D,L Sugars
  4. Configurations of the Aldoses
  5. Cyclic Structures of Monosaccharides: Anomers
  6. Reactions of Monosaccharides
  7. The Eight Essential Monosaccharides
  8. Disaccharides
  9. Polysaccharides and Their Synthesis
  10. Some Other Important Carbohydrates

Biomolecules: Amino Acids, Peptides, and Proteins11 lessons

Chapter page

  1. Structures of Amino Acids
  2. Amino Acids and the Henderson–Hasselbalch Equation: Isoelectric Points
  3. Synthesis of Amino Acids
  4. Peptides and Proteins
  5. Amino Acid Analysis of Peptides
  6. Peptide Sequencing: The Edman Degradation
  7. Peptide Synthesis
  8. Automated Peptide Synthesis: The Merrifield Solid-Phase Method
  9. Protein Structure
  10. Enzymes and Coenzymes
  11. How Do Enzymes Work? Citrate Synthase

Biomolecules: Lipids7 lessons

Chapter page

  1. Waxes, Fats, and Oils
  2. Soap
  3. Phospholipids
  4. Prostaglandins and Other Eicosanoids
  5. Terpenoids
  6. Steroids
  7. Biosynthesis of Steroids

Biomolecules: Nucleic Acids8 lessons

Chapter page

  1. Nucleotides and Nucleic Acids
  2. Base Pairing in DNA
  3. Replication of DNA
  4. Transcription of DNA
  5. Translation of RNA: Protein Biosynthesis
  6. DNA Sequencing
  7. DNA Synthesis
  8. The Polymerase Chain Reaction

The Organic Chemistry of Metabolic Pathways10 lessons

Chapter page

  1. An Overview of Metabolism and Biochemical Energy
  2. Catabolism of Triacylglycerols: The Fate of Glycerol
  3. Catabolism of Triacylglycerols: β-Oxidation
  4. Biosynthesis of Fatty Acids
  5. Catabolism of Carbohydrates: Glycolysis
  6. Conversion of Pyruvate to Acetyl CoA
  7. The Citric Acid Cycle
  8. Carbohydrate Biosynthesis: Gluconeogenesis
  9. Catabolism of Proteins: Deamination
  10. Some Conclusions about Biological Chemistry

Orbitals and Organic Chemistry: Pericyclic Reactions9 lessons

Chapter page

  1. Molecular Orbitals of Conjugated Pi Systems
  2. Electrocyclic Reactions
  3. Stereochemistry of Thermal Electrocyclic Reactions
  4. Photochemical Electrocyclic Reactions
  5. Cycloaddition Reactions
  6. Stereochemistry of Cycloadditions
  7. Sigmatropic Rearrangements
  8. Some Examples of Sigmatropic Rearrangements
  9. A Summary of Rules for Pericyclic Reactions

Synthetic Polymers7 lessons

Chapter page

  1. Chain-Growth Polymers
  2. Stereochemistry of Polymerization: Ziegler–Natta Catalysts
  3. Copolymers
  4. Step-Growth Polymers
  5. Olefin Metathesis Polymerization
  6. Intramolecular Olefin Metathesis
  7. Polymer Structure and Physical Properties