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Organic Chemistry

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Chemistry

Author: Wade Textmap
Publisher: LibreTexts
Source: LibreTexts
License: CC BY-NC-SA
Language: EN
Category: Basic Sciences

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Contents· 384 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
1.05: Octet Rule - Ionic and Covalent Bonding (Review)
1.06: Lewis Structures
1.07: Common Bonding Patterns for Organic Chemistry
1.08: Structural Formulas - Lewis Kekule Bond-line Condensed
1.09: Electronegativity and Bond Polarity (Review)
1.10: Resonance
1.11: Arrhenius Acids and Bases (Review)
1.12: Brnsted-Lowry Acids and Bases (Review)
1.13: Lewis Acids and Bases
1.14: Distinguishing between pH and pKa
1.15: Predicting Relative Acidity
1.16: Molecular Formulas and Empirical Formulas (Review)
1.17: Additional Exercises
1.18: Solutions to Additional Exercises
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
2.09: Organic Functional Groups
2.10: Intermolecular Forces (IMFs) - Review
2.11: Intermolecular Forces
2.12: Intermolecular Forces
2.13: Additional Practice Problems
2.14: Organic Functional Groups: H-bond donors
2.15: Additional Exercises
2.16: 2.15 Solutions to Additional Exercises
03: Structure and Stereochemistry of Alkanes
3.01: Hydrocarbon Functional Groups
3.02: Physical Properties of Alkanes
3.03: Structure and Conformations of Alkanes
3.04: Conformations of Butane
3.05: Conformations of Higher Alkanes
3.06: Cycloalkanes and Ring Strain
3.07: Cyclohexane Conformations
3.08: Conformations of Monosubstituted Cyclohexanes
3.09: Cis-trans Isomerism in Cycloalkanes
3.10: Conformations of Disubstituted Cyclohexanes
3.11: Joined Rings
3.12: Uses and Sources of Alkanes
3.13: Reactions of Alkanes - a Brief Overview
3.14: Additional Exercises
3.15: Solutions to Additional Exercises
04: Stereochemistry at Tetrahedral Centers
4.01: Chirality
4.02: Fischer Projections to communicate Chirality
4.03: Absolute Configuration and the (R) and (S) System
4.04: Diastereomers - more than one chiral center
4.05: Meso Compounds
4.06: Isomerism Summary Diagram
4.07: Optical Activity and Racemic Mixtures
4.08: 6.8 Resolution (Separation) of Enantiomers
4.09: Stereochemistry of Molecules with Three or More Asymmetric Carbons
4.10: Absolute and Relative Configuration - the distinction
4.11: Chirality at Nitrogen, Phosphorus, and Sulfur
4.12: Biochemistry of Enantiomers
4.13: 6.13 The Discovery of Enantiomers
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: 5.2 Reaction Mechanism Notation and Symbols
5.03: 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: 5.7 Reactive Intermediates - Carbocations
5.08: 5.8 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: Alkyl Halides: Nucleophilic Substitution and Elimination
6.01: 7.1 Alkyl Halides - Structure and Physical Properties
6.02: Common Uses of Alkyl Halides
6.03: Preparation of Alkyl Halides
6.04: Reactions of Alkyl Halides: Substitution and Elimination
6.05: The Sₙ2 Reaction
6.06: Characteristics of the Sₙ2 Reaction
6.07: Stereochemistry of the SN2 Reaction
6.08: The Sₙ1 Reaction
6.09: Characteristics of the Sₙ1 Reaction
6.10: Rearrangements of the Carbocation and Sₙ1 Reactions
6.11: The Hammond Postulate and Transition States
6.12: Comparison of SN1 and SN2 Reactions
6.13: Characteristics of the E2 Reaction
6.14: Zaitsev's Rule
6.15: Characteristics of the E1 Reaction
6.16: E2 Regiochemistry and Cyclohexane Conformations
6.17: The E2 Reaction and the Deuterium Isotope Effect
6.18: Comparison of E1 and E2 Reactions
6.19: Comparing Substitution and Elimination Reactions
6.20: Biological Substitution Reactions
6.21: Biological Elimination Reactions
6.22: Additional Exercises
6.23: Solutions to Additional Exercises
07: Structure and Synthesis of Alkenes
7.01: Alkene Structure
7.02: Physical Properties and Important Common Names
7.03: The Alkene Double Bond and Stereoisomerism
7.04: Degrees of Unsaturation
7.05: The E
Z System (when cis
trans does not work)
7.06: Stability of Alkenes
7.07: Alkene Synthesis by Elimination of Alkyl Halides
7.08: Alkene Synthesis by Dehydration of Alcohols
7.09: Uses
7.10: Additional Exercises
7.11: Solutions to Additional Exercises
08: Reactions of Alkenes
8.01: Electrophilic Addition Reactions (EARs)
8.02: Addition of Hydrogen Halides to Symmetrical Alkenes
8.03: Alkene Asymmetry and Markovnikov's Rule
8.04: Hydration: Acid Catalyzed Addition of Water
8.05: Hydration: Oxymercuration-Demercuration
8.06: Hydration: Hydroboration-Oxidation
8.07: Stereochemistry of Reactions - Hydration of Achiral Alkenes
8.08: Stereochemistry of Reactions - Hydration of Chiral Alkenes
8.09: Addition of Halogens
8.10: Formation of Halohydrins
8.11: Reduction of Alkenes - Catalytic Hydrogenation
8.12: Oxidation of Alkenes - Epoxidation
8.13: Dihydroxylation of Alkenes
8.14: Opening of Epoxides - Acidic versus Basic Conditions
8.15: Oxidative Cleavage of Alkenes
8.16: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
8.17: Radical Chain-Growth Polymerization
8.18: 9.18 Biological Additions of Radicals to Alkenes
8.19: Additional Exercises
8.20: Solutions to Additional Exercises
09: Alkynes
9.01: Structure and Physical Properties
9.02: 10.2 Synthesis of Alkynes - Elimination Reactions of Dihalides
9.03: Reactions of Alkynes - Addition of HX and X₂
9.04: Hydration of Alkynes for Markovnikov Products
9.05: Hydration of Alkynes for Anti-Markovnikov Products
9.06: 10.6 Reduction of Alkynes
9.07: Oxidation of Alkynes
9.08: Acidity of Terminal Alkynes
9.09: Synthesis of Larger Alkynes from Acetylides
9.10: An Introduction to Multiple Step Synthesis
9.11: Additional Exercises
9.12: Solutions to Additional Exercises
10: Reactions of Alcohols
10.01: 14.1 Reactions of Alcohols with Hydrohalic Acids
10.02: Reactions with Phosphorus Halides
10.03: Alcohol conversion to Esters - Tosylate and Carboxylate
10.04: Dehydration Reactions of Alcohols
10.05: Oxidation States of Alcohols and Related Functional Groups
10.06: Oxidation Reactions of Alcohols
10.07: Determining Alcohol Classifications in the Lab - alternate reactions
10.08: Protection of Alcohols
10.09: Cleavage of Diols
10.10: Reactions of Alkoxides
10.11: Biological Oxidation - an introduction
10.12: Additional Exercises
10.13: Solutions to Additional Exercises
11: Structure and Synthesis of Alcohols
11.01: Introduction to Structure and Synthesis of Alcohols
11.02: Classification of Alcohols
11.03: Physical Properties of Alcohols
11.04: Spectroscopy of Alcohols
11.05: Acidity of Alcohols and Phenols
11.06: Synthesis of Alcohols - Review
11.07: Reduction of the Carbonyl Group - Synthesis of 1º and 2º Alcohols
11.08: Organometallic Reagents
11.09: Organometallic Reagents in Alcohol Synthesis
11.10: Thiols (Mercaptans)
11.11: Commercially Important Alcohols
11.12: 13.12 Additional Exercises
11.13: Solutions to Additional Exercises
12: Infrared Spectroscopy and Mass Spectrometry
12.01: The Electromagnetic Spectrum
12.02: Infrared (IR) Spectroscopy
12.03: IR-Active and IR-Inactive Vibrations
12.04: Interpretting IR Spectra
12.05: Infrared Spectra of Some Common Functional Groups
12.06: Summary and Tips to Distinguish between Carbonyl Functional Groups
12.07: Mass Spectrometry - an introduction
12.08: Fragmentation Patterns in Mass Spectrometry
12.09: Useful Patterns for Structure Elucidation
12.10: Determination of the Molecular Formula by High Resolution Mass Spectrometry
13: Nuclear Magnetic Resonance Spectroscopy
13.01: Theory of Nuclear Magnetic Resonance (NMR)
13.02: NMR Spectra - an introduction
13.03: Chemical Shifts and Shielding
13.04: ¹H NMR Spectroscopy and Proton Equivalence
13.05: Functional Groups and Chemical Shifts in ¹H NMR Spectroscopy
13.06: Integration of ¹H NMR Absorptions: Proton Counting
13.07: Spin-Spin Splitting in ¹H NMR Spectra
13.08: More Complex Spin-Spin Splitting Patterns
13.09: Uses of ¹H NMR Spectroscopy
13.10: ¹³C NMR Spectroscopy
13.11: Chemical Shifts and Interpreting ¹³C NMR Spectra
13.12: ¹³C NMR Spectroscopy
13.13: Uses of ¹³C NMR Spectroscopy
13.14: More NMR Examples
13.15: Sample NMR Spectra
14: Ethers Epoxides and Thioethers
14.01: Physical Properties of Ethers
14.02: Spectroscopy of Ethers
14.03: The Williamson Ether Synthesis
14.04: Alkoxymercuration-Demercuration Synthesis of Ethers
14.05: Acidic Cleavage of Ethers
14.06: Autoxidation of Ethers
14.07: Synthesis of Epoxides
14.08: Opening of Epoxides
14.09: Reactions of Epoxides with Grignard and Organolithium Reagents
14.10: Crown Ethers
14.11: Epoxy Resins: The Advent of Modern Glues
14.12: Thioethers (Sulfides) and Silyl Ethers
14.13: Additional Exercises
14.14: Solutions to Additional Exercises
15: Conjugated Systems Orbital Symmetry and Ultraviolet Spectroscopy
15.01: Stability of Conjugated Dienes - Molecular Orbital Theory
15.02: Allylic Cations
15.03: Electrophilic Additions to Conjugated Dienes
15.04: Kinetic versus Thermodynamic Control
15.05: SN2 Reactions of Allylic Halides and Tosylates
15.06: The Diels-Alder (4 2) Cycloaddition Reaction
15.07: Diels-Alder Stereochemistry
15.08: Diene Polymers - Natural and Synthetic Rubbers
15.09: Structure Determination in Conjugated Systems - Ultraviolet Spectroscopy
15.10: Interpreting Ultraviolet Spectra - The Effect of Conjugation
15.11: 16.11:Conjugation, Color, and the Chemistry of Vision
15.12: Additional Exercises
15.13: Solutions to Additional Exercises
16: Aromatic Compounds
16.01: Introduction: The Discovery of Benzene
16.02: The Structure and Properties of Benzene and its Derivatives
16.03: Resonance and the Molecular Orbitals of Benzene
16.04: The Molecular Orbital Picture of Cyclobutadiene
16.05: Aromaticity and Huckel's Rule
16.06: Aromatic Ions - a closer look
16.07: Heterocyclic Aromatic Compounds - a closer look
16.08: Polycyclic Aromatic Hydrocarbons
16.09: Spectroscopy of Aromatic Compounds
16.10: Additional Exercises
16.11: Solutions to Additional Exercises
17: Reactions of Aromatic Compounds
17.01: Electrophilic Aromatic Substitution (EAS)
17.02: Halogenation of Benzene (an EAS Reaction)
17.03: Nitration of Benzene (an EAS Reaction)
17.04: Sulfonation of Benzene (an EAS Reaction)
17.05: Alkylation and Acylation of Benzene - The Friedel-Crafts EAS Reactions
17.06: Substituent Effects on the EAS Reaction
17.07: Side-Chain Reactions of Benzene Derivatives
17.08: Synthetic Strategies for Di-substituted Benzenes
17.09: Trisubstituted Benzenes - Effects of Multiple Substituents
17.10: Nucleophilic Aromatic Substitution - The Addition-Elimantion Mechanism
17.11: NAS Reactions - the Elimination-Addition (Benzyne) Mechanism
17.12: Reduction of Aromatic Compounds
17.13: Additional Exercises
17.14: Solutions to Additional Exercises
18: Ketones and Aldehydes
18.01: Carbonyl Compound Structure and Properties
18.02: Spectroscopy of Ketones and Aldehydes
18.03: Review of Ketone and Aldehyde Synthesis
18.04: 19.4 New Synthesis of Aldehydes and Ketones
18.05: Nucleophilic Addition Reactions of Ketones and Aldehydes
18.06: Nucleophilic Addition of Water (Hydration)
18.07: Nucleophilic Addition of Cyanide and Acetylide
18.08: Nucleophilic Addition of Grignards
18.09: Nucelophilic Addition of Amines (Imine and Enamine Formation)
18.10: Nucleophilic Addition of Hydrazine (Wolff-Kishner Reaction)
18.11: Nucelophilic Addition of Alcohols (Acetal Formation)
18.12: Acetals as Protecting Groups
18.13: Nucelophilic Addition of Phosphorus Ylides (The Wittig Reaction)
18.14: Oxidation of Aldehydes
18.15: Reductions of Ketones and Aldehydes
18.16: Additional Exercises
18.17: Solutions to Additional Exercises
19: Carboxylic Acids
19.01: Structure and Properties of Carboxylic Acids and their Salts
19.02: Acidity of Carboxylic Acids
19.03: Spectroscopy of Carboxylic Acids
19.04: Synthesis of Carboxylic Acids
19.05: Reactions of Carboxylic Acids Overview
19.06: Condensation of Acids with Alcohols: The Fischer Esterification
19.07: Methyl Ester Synthesis Using Diazomethane
19.08: Condensation of Acids with Amines
19.09: Reduction of Carboxylic Acids
19.10: Biochemically Interesting Carboxylic Acids
19.11: Additional Exercises
19.12: Solutions to Additional Exercises
20: Carboxylic Acid Derivatives and Nitriles
20.01: Structure and Physical Properties of Acid Derivatives
20.02: Spectroscopy of Carboxylic Acid Derivatives
20.03: Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution
20.04: Acid Halide Chemistry
20.05: Acid Anhydride Chemistry
20.06: Ester Chemistry
20.07: Amide Chemistry
20.08: Nitrile Chemistry
20.09: Thioesters: Biological Carboxylic Acid Derivatives
20.10: Polyamides and Polyesters: Step-Growth Polymers
20.11: Beta-Lactams: An Application
20.12: Biological Acylation Reactions
20.13: Additional Exercises
20.14: Solutions to Additional Exercises
21: Alpha Substitutions and Condensations of Carbonyl Compounds
21.01: Relative Acidity of alpha-Hydrogens
21.02: Enols, Enolate Ions and Tautomerization
21.03: Reaction Overview
21.04: Alpha Halogenation of Carbonyls
21.05: Bromination of Acids: The HVZ Reaction
21.06: Alkylation of the alpha-Carbon via the LDA pathway
21.07: Alkylation of the Alpha-Carbon via the Enamine Pathway
21.08: The Aldol Reaction and Condensation of Ketones and Aldehydes
21.09: The Claisen Condensation Reactions of Esters
21.10: Conjugate Additions: The Michael Reaction
21.11: Decarboxylation Reactions
21.12: Additional Exercises
21.13: Solutions to Additional Exercises
22: Amines
22.01: Structure and Physical Properties of Amines
22.02: Basicity of Amines and Ammonium Salt Formation
22.03: Spectroscopy of Amines
22.04: Synthesis of Amines
22.05: Synthesis of Primary Amines
22.06: Reactions of Amines
22.07: Reactions of Arylamines
22.08: The Hofmann Elimination: Amines as Leaving Groups
22.09: Oxidation of Amines - The Cope Elimination
22.10: Sulfa Drugs - a closer look
22.11: Additional Exercises
22.12: Solutions to Additional Exercises
23: Carbohydrates
23.01: Introduction
23.02: Classification of Carbohydrates
23.03: Fischer Projections
23.04: D and L Sugars
23.05: Configuration of Aldoses
23.06: Cyclic Structures of Monosaccharides
23.07: Reactions of Monosaccharides
23.08: Disaccharides and Glycosidic Bonds
23.09: Polysaccharides
23.10: Other Important Carbohydrates
23.11: Cell Surface Carbohydrates and Influenza Viruses
24: Amino Acids Peptides and Proteins
24.01: Introduction
24.02: Structure and Stereochemistry of the Amino Acids
24.03: Isoelectric Points and Electrophoresis
24.04: Synthesis of Amino Acids
24.05: Peptides and Proteins
24.06: Amino Acid Analysis of Peptides
24.07: Peptide Sequencing: The Edman Degradation
24.08: Peptide Synthesis
24.09: Automated Peptide Synthesis: The Merrifield Solid-Phase Technique
24.10: Levels of Protein Structure
24.11: Enzymes and Coenzymes
24.12: How do enzymes work?
25: Lipids
25.1: Introduction
25.2: Waxes, Fats, and Oils
25.3: Saponification of Fats and Oils; Soaps and Detergents
25.4: Phospholipids
25.5: Prostaglandins and other Eicosanoids
25.6: Terpenes and Terpenoids
25.7: Steroids
25.8: Biosynthesis of Steroids
26: Nucleic Acids
26.1: Nucleotides and Nucleic Acids
26.2: DNA Base Pairs
26.3: DNA Replication
26.4: Transcription of DNA
26.5: Translation of RNA: Protein Biosynthesis
26.6: DNA Sequencing
26.7: Polymerase Chain Reactions
27: Front Matter
27.1: Table of Contents
28: Back Matter