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Organic Chemistry

Organic chemistry studies the structure, properties and reactions of organic compounds, which contain carbon in covalent bonding. Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and theoretically.

Organic Chemistry Chemistry

Author: Morsch et al.
Publisher: LibreTexts
Source: LibreTexts
License: CC BY-SA
Language: EN
Category: Basic Sciences

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Contents· 388 sections

01: Structure and Bonding
1.00: Introduction to Organic Chemistry
1.01: Atomic Structure - The Nucleus
1.02: Atomic Structure - Orbitals
1.03: Atomic Structure - Electron Configurations
1.04: Development of Chemical Bonding Theory
1.05: Describing Chemical Bonds - Valence Bond Theory
1.06: sp Hybrid Orbitals and the Structure of Methane
1.07: sp Hybrid Orbitals and the Structure of Ethane
1.08: sp Hybrid Orbitals and the Structure of Ethylene
1.09: sp Hybrid Orbitals and the Structure of Acetylene
1.10: Hybridization of Nitrogen Oxygen Phosphorus and Sulfur
1.11: Describing Chemical Bonds - Molecular Orbital Theory
1.12: Drawing Chemical Structures
1.S: Structure and Bonding (Summary)
02: Polar Covalent Bonds Acids and Bases
2.00: Polar Covalent Bonds - Electronegativity
2.01: Polar Covalent Bonds - Dipole Moments
2.02: Formal Charges
2.03: Resonance
2.04: Rules for Resonance Forms
2.05: Drawing Resonance Forms
2.06: Acids and Bases - The Brnsted-Lowry Definition
2.07: Acid and Base Strength
2.08: Predicting Acid-Base Reactions from pKa Values
2.09: Organic Acids and Organic Bases
2.10: Acids and Bases - The Lewis Definition
2.11: Noncovalent Interactions Between Molecules
2.MM: Molecular Models
2.S: Polar Covalent Bonds Acids and Bases (Summary)
03: Organic Compounds- Alkanes and Their Stereochemistry
3.00: Chapter Objectives
3.01: Functional Groups
3.02: Alkanes and Alkane Isomers
3.03: Alkyl Groups
3.04: Naming Alkanes
3.05: Properties of Alkanes
3.06: Conformations of Ethane
3.07: Conformations of Other Alkanes
3.08: Gasoline - A Deeper Look
3.S: Organic Compounds- Alkanes and Their Stereochemistry (Summary)
04: Organic Compounds - Cycloalkanes and their Stereochemistry
4.00: Chapter Objectives
4.01: Naming Cycloalkanes
4.02: Cis-Trans Isomerism in Cycloalkanes
4.03: Stability of Cycloalkanes - Ring Strain
4.04: Conformations of Cycloalkanes
4.05: Conformations of Cyclohexane
4.06: Axial and Equatorial Bonds in Cyclohexane
4.07: Conformations of Monosubstituted Cyclohexanes
4.08: Conformations of Disubstituted Cyclohexanes
4.09: Conformations of Polycyclic Molecules
4.S: Organic Compounds- Cycloalkanes and their Stereochemistry (Summary)
05: Stereochemistry at Tetrahedral Centers
5.00: Chapter Objectives and Introduction
5.01: Enantiomers and the Tetrahedral Carbon
5.02: The Reason for Handedness in Molecules - Chirality
5.03: Optical Activity
5.04: Pasteur's Discovery of Enantiomers
5.05: Sequence Rules for Specifying Configuration
5.06: Diastereomers
5.07: Meso Compounds
5.08: Racemic Mixtures and the Resolution of Enantiomers
5.09: A Review of Isomerism
5.10: Chirality at Nitrogen Phosphorus and Sulfur
5.11: Prochirality
5.12: Chirality in Nature and Chiral Environments
5.S: Stereochemistry at Tetrahedral Centers (Summary)
5.xx: Enantiomers and Diastereomers
06: An Overview of Organic Reactions
6.00: Chapter Objectives
6.01: Kinds of Organic Reactions
6.02: How Organic Reactions Occur - Mechanisms
6.03: Radical Reactions
6.04: Polar Reactions
6.05: An Example of a Polar Reaction - Addition of HBr to Ethylene
6.06: Using Curved Arrows in Polar Reaction Mechanisms
6.07: Describing a Reaction - Equilibria Rates and Energy Changes
6.08: Describing a Reaction - Bond Dissociation Energies
6.09: Describing a Reaction - Energy Diagrams and Transition States
6.10: Describing a Reaction - Intermediates
6.11: A Comparison between Biological Reactions and Laboratory Reactions
6.S: An Overview of Organic Reactions (Summary)
07: Alkenes- Structure and Reactivity
7.00: Chapter Objectives
7.01: Introduction to Alkenes
7.02: Industrial Preparation and Use of Alkenes
7.03: Calculating Degree of Unsaturation
7.04: Naming Alkenes
7.05: Cis-Trans Isomerism in Alkenes
7.06: Sequence Rules - The EZ Designation
7.07: Stability of Alkenes
7.08: Electrophilic Addition Reactions of Alkenes
7.09: Orientation of Electrophilic Additions - Markovnikov's Rule
7.10: Carbocation Structure and Stability
7.11: The Hammond Postulate
7.12: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements
7.S: Alkenes- Structure and Reactivity (Summary)
08: Alkenes- Reactions and Synthesis
8.00: Chapter Objectives
8.01: Preparation of Alkenes - A Preview of Elimination Reactions
8.02: Halogenation of Alkenes - Addition of X
8.03: Halohydrins from Alkenes - Addition of HOX
8.04: Hydration of Alkenes - Addition of HO by Oxymercuration
8.05: Hydration of Alkenes - Addition of HO by Hydroboration
8.06: Reduction of Alkenes - Hydrogenation
8.07: Oxidation of Alkenes - Epoxidation and Hydroxylation
8.08: Oxidation of Alkenes - Cleavage to Carbonyl Compounds
8.09: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
8.10: Radical Additions to Alkenes - Chain-Growth Polymers
8.11: Biological Additions of Radicals to Alkenes
8.12: Stereochemistry of Reactions - Addition of HO to an Achiral Alkene
8.13: Stereochemistry of Reactions - Addition of HO to a Chiral Alkene
8.S: Alkenes - Reactions and Synthesis (Summary)
09: Alkynes - An Introduction to Organic Synthesis
9.00: Chapter Objectives
9.01: Naming Alkynes
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.S: Alkynes - An Introduction to Organic Synthesis (Summary)
10: Organohalides
10.00: Introduction to Organohalides
10.01: Names and Properties of Alkyl Halides
10.02: Preparing Alkyl Halides from Alkanes - Radical Halogenation
10.03: Preparing Alkyl Halides from Alkenes - Allylic Bromination
10.04: Stability of the Allyl Radical - Resonance Revisited
10.05: Preparing Alkyl Halides from Alcohols
10.06: Reactions of Alkyl Halides - Grignard Reagents
10.07: Organometallic Coupling Reactions
10.08: Oxidation and Reduction in Organic Chemistry
10.S: Organohalides (Summary)
11: Reactions of Alkyl Halides- Nucleophilic Substitutions and Eliminations
11.00: Introduction
11.01: The Discovery of Nucleophilic Substitution Reactions
11.02: The SN2 Reaction
11.03: Characteristics of the SN2 Reaction
11.04: The SN1 Reaction
11.05: Characteristics of the SN1 Reaction
11.06: Biological Substitution Reactions
11.07: Elimination Reactions- Zaitsev's Rule
11.08: The E2 Reaction and the Deuterium Isotope Effect
11.09: The E2 Reaction and Cyclohexane Conformation
11.10: The E1 and E1cB Reactions
11.11: Biological Elimination Reactions
11.12: A Summary of Reactivity - SN1 SN2 E1 E1cB and E2
11.S: Reactions of Alkyl Halides - Nucleophilic Substitutions and Eliminations (Summary)
12: Structure Determination - Mass Spectrometry and Infrared Spectroscopy
12.00: Introduction
12.01: Mass Spectrometry of Small Molecules - Magnetic-Sector Instruments
12.02: Interpreting Mass Spectra
12.03: Mass Spectrometry of Some Common Functional Groups
12.04: Mass Spectrometry in Biological - Time-of-flight (TOF) Instruments
12.05: Spectroscopy and the Electromagnetic Spectrum
12.06: Infrared Spectroscopy
12.07: Interpreting Infrared Spectra
12.08: Infrared Spectra of Some Common Functional Groups
12.S: Structure Determination - Mass Spectrometry and Infrared Spectroscopy (Summary)
13: Structure Determination - Nuclear Magnetic Resonance Spectroscopy
13.00: Nuclear Magnetic Resonance Spectroscopy
13.01: The Nature of NMR Absorptions
13.02: The Chemical Shift
13.03: Chemical Shifts in H NMR Spectroscopy
13.04: Integration of H NMR Absorptions- Proton Counting
13.05: Spin-Spin Splitting in H NMR Spectra
13.06: H NMR Spectroscopy and Proton Equivalence
13.07: More Complex Spin-Spin Splitting Patterns
13.08: Uses of H NMR Spectroscopy
13.09: C NMR Spectroscopy - Signal Averaging and FT-NMR
13.10: Characteristics of C NMR Spectroscopy
13.11: DEPT C NMR Spectroscopy
13.12: Uses of C NMR Spectroscopy
13.S: Structure Determination - Nuclear Magnetic Resonance Spectroscopy (Summary)
14: Conjugated Compounds and Ultraviolet Spectroscopy
14.00: Introduction
14.01: Stability of Conjugated Dienes- Molecular Orbital Theory
14.02: Electrophilic Additions to Conjugated Dienes- Allylic Carbocations
14.03: Kinetic vs. Thermodynamic Control of Reactions
14.04: The Diels-Alder Cycloaddition Reaction
14.05: Characteristics of the Diels-Alder Reaction
14.06: Diene Polymers- Natural and Synthetic Rubbers
14.07: Structure Determination in Conjugated Systems - Ultraviolet Spectroscopy
14.08: Interpreting Ultraviolet Spectra- The Effect of Conjugation
14.09: Conjugation Color and the Chemistry of Vision
14.S: Conjugated Compounds and Ultraviolet Spectroscopy (Summary)
15: Benzene and Aromaticity
15.00: Introduction
15.01: Naming Aromatic Compounds
15.02: Structure and Stability of Benzene
15.03: Aromaticity and the Huckel 4n 2 Rule
15.04: Aromatic Ions
15.05: Aromatic Heterocycles - Pyridine and Pyrrole
15.06: Polycyclic Aromatic Compounds
15.07: Spectroscopy of Aromatic Compounds
15.S: Benzene and Aromaticity (Summary)
16: Chemistry of Benzene - Electrophilic Aromatic Substitution
16.00: Introduction
16.01: Electrophilic Aromatic Substitution Reactions - Bromination
16.02: Other Aromatic Substitutions
16.03: Alkylation and Acylation of Aromatic Rings - The Friedel-Crafts Reaction
16.04: Substituent Effects in Substituted Aromatic Rings
16.05: An Explanation of Substituent Effects
16.06: Trisubstituted Benzenes - Additivity of Effects
16.07: Nucleophilic Aromatic Substitution
16.08: Benzyne
16.09: Oxidation of Aromatic Compounds
16.10: Reduction of Aromatic Compounds
16.11: Synthesis of Polysubstituted Benzenes
16.S: Chemistry of Benzene - Electrophilic Aromatic Substitution (Summary)
17: Alcohols and Phenols
17.00: Introduction to Alcohols and Phenols
17.01: Naming Alcohols and Phenols
17.02: Properties of Alcohols and Phenols
17.03: Preparation of Alcohols- A Review
17.04: Alcohols from Carbonyl Compounds- Reduction
17.05: Alcohols from Carbonyl Compounds - Grignard Reagents
17.06: Reactions of Alcohols
17.07: Oxidation of Alcohols
17.08: Protection of Alcohols
17.09: Phenols and Their Uses
17.10: Reactions of Phenols
17.11: Spectroscopy of Alcohols and Phenols
17.S: Alcohols and Phenols (Summary)
18: Ethers and Epoxides Thiols and Sulfides
18.00: Introduction
18.01: Names and Properties of Ethers
18.02: Preparing Ethers
18.03: Reactions of Ethers - Acidic Cleavage
18.04: Reactions of Ethers - Claisen Rearrangement
18.05: Cyclic Ethers - Epoxides
18.06: Reactions of Epoxides - Ring-opening
18.07: Crown Ethers
18.08: Thiols and Sulfides
18.09: Spectroscopy of Ethers
18.10: Interchapter - A Preview of Carbonyl Chemistry
18.S: Ethers and Epoxides Thiols and Sulfides (Summary)
19: Aldehydes and Ketones- Nucleophilic Addition Reactions
19.00: Chapter Objectives and Preview of Carbonyl Chemistry
19.01: Naming Aldehydes and Ketones
19.02: Preparing Aldehydes and Ketones
19.03: Oxidation of Aldehydes and Ketones
19.04: Nucleophilic Addition Reactions of Aldehydes and Ketones
19.05: Nucleophilic Addition of Water- Hydration
19.06: Nucleophilic Addition of HCN- Cyanohydrin Formation
19.07: Nucleophilic Addition of Hydride and Grignard Reagents - Alcohol Formation
19.08: Nucleophilic Addition of Amines - Imine and Enamine Formation
19.09: Nucleophilic Addition of Hydrazine - The Wolff-Kishner Reaction
19.10: Nucleophilic Addition of Alcohols - Acetal Formation
19.11: Nucleophilic Addition of Phosphorus Ylides - The Wittig Reaction
19.12: Biological Reductions
19.13: Conjugate Nucleophilic Addition to -unsaturated Aldehydes and Ketones
19.14: Spectroscopy of Aldehydes and Ketones
19.S: Aldehydes and Ketones (Summary)
20: Carboxylic Acids and Nitriles
20.00: Chapter Objectives and Introduction to Carboxylic Acids
20.01: Naming Carboxylic Acids and Nitriles
20.02: Structure and Properties of Carboxylic Acids
20.03: Biological Acids and the Henderson-Hasselbalch Equation
20.04: Substituent Effects on Acidity
20.05: Preparing Carboxylic Acids
20.06: Reactions of Carboxylic Acids - An Overview
20.07: Chemistry of Nitriles
20.08: Spectroscopy of Carboxylic Acids and Nitriles
20.S: Carboxylic Acids and Nitriles (Summary)
21: Carboxylic Acid Derivatives- Nucleophilic Acyl Substitution Reactions
21.00: Chapter Objectives and Introduction to Carboxylic Acid Derivatives
21.01: Naming Carboxylic Acid Derivatives
21.02: Nucleophilic Acyl Substitution Reactions
21.03: Nucleophilic Acyl Substitution Reactions of Carboxylic Acids
21.04: Chemistry of Acid Halides
21.05: Chemistry of Acid Anhydrides
21.06: Chemistry of Esters
21.07: Chemistry of Amides
21.08: Chemistry of Thioesters and Acyl Phosphates - Biological Carboxylic Acid Derivatives
21.09: Polyamides and Polyesters - Step-Growth Polymers
21.10: Spectroscopy of Carboxylic Acid Derivatives
21.S: Carboxylic Acid Derivatives (Summary)
22: Carbonyl Alpha-Substitution Reactions
22.00: Chapter Objectives and Introduction to Carbonyl Alpha-Substitution Reactions
22.01: Keto-Enol Tautomerism
22.02: Reactivity of Enols- The Mechanism of Alpha-Substitution Reactions
22.03: Alpha Halogenation of Aldehydes and Ketones
22.04: Alpha Bromination of Carboxylic Acids
22.05: Acidity of Alpha Hydrogen Atoms- Enolate Ion Formation
22.06: Reactivity of Enolate Ions
22.07: Alkylation of Enolate Ions
22.S: Carbonyl Alpha-Substitution Reactions (Summary)
23: Carbonyl Condensation Reactions
23.00: Chapter Objectives
23.01: Carbonyl Condensations - The Aldol Reaction
23.02: Carbonyl Condensations versus Alpha Substitutions
23.03: Dehydration of Aldol Products - Synthesis of Enones
23.04: Using Aldol Reactions in Synthesis
23.05: Mixed Aldol Reactions
23.06: Intramolecular Aldol Reactions
23.07: The Claisen Condensation Reaction
23.08: Mixed Claisen Condensations
23.09: Intramolecular Claisen Condensations - The Dieckmann Cyclization
23.10: Conjugate Carbonyl Additions - The Michael Reaction
23.11: Carbonyl Condensations with Enamines - The Stork Reaction
23.12: The Robinson Annulation Reaction
23.13: Some Biological Carbonyl Condensation Reactions
23.S: Carbonyl Condensation Reactions (Summary)
24: Amines and Heterocycles
24.00: Chapter Objectives
24.01: Naming Amines
24.02: Structure and Properties of Amines
24.03: Basicity of Amines
24.04: Basicity of Arylamines
24.05: Biological Amines and the Henderson-Hasselbalch Equation
24.06: Synthesis of Amines
24.07: Reactions of Amines
24.08: Reactions of Arylamines
24.09: Heterocyclic Amines
24.10: Spectroscopy of Amines
24.S: Amines and Heterocycles (Summary)
25: Biomolecules- Carbohydrates
25.00: Introduction
25.01: Classification of Carbohydrates
25.02: Depicting Carbohydrate Stereochemistry - Fischer Projections
25.03: D L Sugars
25.04: Configurations of Aldoses
25.05: Cyclic Structures of Monosaccharides - Anomers
25.06: Reactions of Monosaccharides
25.07: The Eight Essential Monosaccharides
25.08: Disaccharides
25.09: Polysaccharides and Their Synthesis
25.10: Other Important Carbohydrates
25.11: Cell-Surface Carbohydrates and Influenza Viruses
25.S: Biomolecules- Carbohydrates (Summary)
26: Biomolecules- Amino Acids Peptides and Proteins
26.00: Chapter Objectives
26.01: Introduction
26.02: Structures of Amino Acids
26.03: Amino Acids the Henderson-Hasselbalch Equation and Isoelectric Points
26.04: Synthesis of Amino Acids
26.05: Peptides and Proteins
26.06: Amino Acid Analysis of Peptides
26.07: The Edman Degradation
26.08: Peptide Synthesis
26.09: The Merrifield Solid-Phase Technique
26.10: Protein Structure
26.11: Enzymes and Coenzymes
26.12: How do Enzymes Work Citrate Synthase
27: Biomolecules - Lipids
27.00: Introduction to Lipids
27.01: Waxes Fats and Oils
27.02: Soap
27.03: Phospholipids
27.04: Prostaglandins and Other Eicosanoids
27.05: Terpenoids
27.06: Steroids
27.07: Biosynthesis of Steroids
27.S: Biomolecules - Lipids (Summary)
28: Biomolecules - Nucleic Acids
28.00: Chapter Objectives
28.01: Nucleotides and Nucleic Acids
28.02: Base Pairing in DNA - The Watson-Crick Model
28.03: Replication of DNA
28.04: Transcription of DNA
28.05: Translation of RNA - Protein Biosynthesis
28.06: DNA Sequencing
28.07: DNA Synthesis
28.08: The Polymerase Chain Reaction
29: Orbitals and Organic Chemistry - Pericyclic Reactions
29.00: Chapter Overview
29.01: Molecular Orbitals of Conjugated Pi Systems
29.02: Electrocyclic Reactions
29.03: Stereochemistry of Thermal Electrocyclic Reactions
29.04: Photochemical Electrocyclic Reactions
29.05: Cycloaddition Reactions
29.06: Stereochemistry of Cycloadditions
29.07: Sigmatropic Rearrangements
29.08: Some Examples of Sigmatropic Rearrangements
29.09: A Summary of Rules for Pericyclic Reactions
30: Synthetic Polymers
30.00: Chapter Objectives
30.01: Chain-Growth Polymers
30.02: Stereochemistry of Polymerization- Ziegler-Natta Catalysts
30.03: Copolymers
30.04: Step-Growth Polymers
30.05: Olefin Metathesis Polymerization
30.06: Polymer Structure and Physical Properties