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Basic Principles of Organic Chemistry

This general organic Textmap by John D. Robert and Marjorie C. Caserio emphasizes thermochemistry to aid the undergraduate's understanding of organic reactions

Organic Chemistry Chemistry

Author: John D. Roberts and Marjorie C. Caserio
Publisher: California Institute of Technology
Source: LibreTexts
Language: EN
Category: Basic Sciences

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Contents· 361 sections

01: Introduction to Organic Chemistry
1.01: Prelude to Organic Chemistry
1.02: A Bit of History
1.03: What Preparation Should You Have
1.04: Why Is Organic Chemistry Special
1.05: The Breadth of Organic Chemistry
1.06: Some Philosophical Observations
1.E: Introduction to Organic Chemistry (Exercises)
02: Structural Organic Chemistry
2.01: Structural Formulas
2.02: The Sizes and Shapes of Organic Molecules
2.03: Classification by Functional Groups
2.04: Isomerization in Organic Compounds
2.E: Structural Organic Chemistry (Exercises)
03: Organic Nomenclature
3.01: Prelude to Organic Nomenclature
3.02: Alkanes
3.03: Cycloalkanes
3.04: Alkenes Cycloalkenes and Alkadienes
3.05: Alkynes
3.06: Arenes
3.E: Organic Nomenclature (Exercises)
04: Alkanes
4.01: Prelude to Alkanes
4.02: Physical Properties of Alkanes and The Concept of Homology
4.03: Chemical Reactions of Alkanes. Combustion of Alkanes
4.04: Combustion. Heats of Reaction. Bond Energies
4.05: Halogenation of Alkanes. Energies and Rates of Reactions
4.06: Practical Halogenations and Problems of Selectivity
4.07: Nitration of Alkanes
4.E: Alkanes (Exercises)
05: Stereoisomerism of Organic Molecules
5.01: Prelude to Stereoisomerism
5.02: Configurational Isomers
5.03: Conformational Isomers
5.04: Representation of Organic Structure
5.05: The D L Convention for Designating Stereochemical Configurations
5.06: Molecules with More Than One Chiral Center. Diastereomers
5.07: Some Examples of the Importance of Stereoisomerism to Biology. Biological Stereospeciflcity
5.E: Stereoisomerism of Organic Molecules (Exercises)
06: Bonding in Organic Molecules
6.01: Prelude to Bonding
6.02: Hydrogenlike Atomic Orbitals
6.03: Bond Formation Using Atomic Orbitals
6.04: Electron Repulsion and Bond Angles. Orbital Hybridization
6.05: Atomic-Orbital Models
6.06: Resonance
6.07: Advanced Quantum Theory of Organic Molecules
6.E: Bonding in Organic Molecules (Exercises)
07: Other Compounds than Hydrocarbons
7.01: General Approaches to Naming Organic Compounds
7.02: Alcohols and Phenols- ROH ArOH
7.03: Ethers ROR'
7.04: Aldehydes
7.05: Ketones RCOR'
7.06: Carboxylic Acids
7.07: Acyl Groups RCO-
7.08: Amines
7.09: Nitriles RCN
7.10: The Use of Greek Letters to Denote Substituent Positions
7.11: Single- or Multiple-Word Names
7.E: Other Compounds than Hydrocarbons (Exercises)
08: Nucleophilic Substitution and Elimination Reactions
8.01: Prelude to Nucleophilic Substitution and Elimination Reactions
8.02: Classification of Reagents as Electrophiles and Nucleophiles. Acids and Bases
8.03: Thermochemistry of Substitution Reactions
8.04: General Considerations of Substitution Reactions
8.05: Mechanisms of Nucleophilic Substitution Reactions
8.06: Stereochemistry of (S N2) Reactions
8.07: Stereochemistry of (S N1) Reactions
8.08: Structural and Solvent Effects in (S N) Reactions
8.09: The E2 Reaction
8.10: The E1 Reaction
8.11: Elimination Reactions
8.E: Nucleophilic Substitution and Elimination Reactions (Exercises)
09: Separation Purification and Identification of Organic Compounds
9.01: Prelude to Separation Purification and Identification
9.02: How do we know when an Organic Compounds is Pure
9.03: Chromatographic Separation Procedures
9.04: Why Can't We See Molecules
9.05: Atomic Energy States and Line Spectra
9.06: Energy States of Molecules
9.07: Microwave (Rotational) Spectra
9.08: Infrared (Rovibrational) Spectroscopy
9.09: Raman Spectroscopy
9.10: Electronic Spectra of Organic Molecules
9.11: Nuclear Magnetic Resonance Spectroscopy
9.12: Mass Spectroscopy
9.E: Separation Purification and Identification of Organic Compounds (Exercises)
10: Alkenes and Alkynes I - Ionic and Radical Addition Reactions
10.01: Prelude to Alkenes and Alkynes
10.02: Physical and Spectroscopic Properties of Alkenes and Alkynes
10.03: The Reactivity of Multiple Carbon-Carbon Bonds
10.04: Electrophilic Additions to Alkenes
10.05: Orientation in Addition to Alkenes
10.06: Electrophilic Addition Reactions of Alkynes
10.07: Nucleophilic Addition Reactions
10.08: Radical-Chain Addition Reactions to Alkenes
10.09: Polymerization of Alkenes
10.10: Alkylation of Alkenes
10.E: Alkenes and Alkynes I (Exercises)
11: Alkenes and Alkynes II - Oxidation and Reduction Reactions. Acidity of Alkynes
11.01: Oxidation-Reduction of Organic Compounds
11.02: Hydrogenation with Heterogeneous Catalysts
11.03: Heats of Hydrogenation
11.04: Hydrogenation with Homogeneous Catalysts
11.05: Hydrogenation with Diimide
11.06: Addition of Boron Hydrides to Alkenes. Organoboranes
11.07: Oxidation Reactions
11.08: Terminal Alkynes as Acids
11.E: Alkenes and Alkynes II (Exercises)
12: Cycloalkanes Cycloalkenes and Cycloalkynes
12.01: Nomenclature and Physical Properties of Cycloalkanes
12.02: Spectroscopic Properties of Cyclohexanes
12.03: Conformations of Cycloalkanes
12.04: Strain in Cycloalkane Rings
12.05: Chemical Properties
12.06: The Larger Cycloalkanes and their Conformations
12.07: Cycloalkenes and Cycloalkanes
12.08: Nomenclature of Polycycloalkanes
12.09: Conformations of Decalin
12.10: Strain in Polycyclic Molecules
12.E: Cycloalkanes Cycloalkenes and Cycloalkynes (Exercises)
13: Polyfunctional Compounds Alkadienes and Approaches to Organic Synthesis
13.01: General Comments on Alkadienes
13.02: 13- or Conjugated Dienes. Electrophilic and Radical Addition
13.03: Cycloaddition Reactions
13.04: Polymerization Reactions of Conjugated Dienes
13.05: Cumulated Alkadienes
13.06: Approaches to Planning Practical Organic Syntheses
13.07: Building the Carbon Skeleton
13.08: Introducing Functionality
13.09: Construction of Ring Systems by Cycloaddition
13.10: Protecting Groups in Organic Synthesis
13.11: Building the Carbon Skeleton
13.E: Polyfunctional Compounds Alkadienes and Approaches to Organic Synthesis (Exercises)
14: Organohalogen and Organometallic Compounds
14.01: Prelude to Organohalogen and Organometallic Compounds
14.02: Physical Properties of Organohalogen and Organometallic Compounds
14.03: Spectroscopic Properties
14.04: Alkyl Halides
14.05: Alkenyl and Alkynyl Halides
14.06: Cycloalkyl Halides
14.07: Aryl Halides
14.08: Polyhalogenated Alkanes and Alkenes
14.09: Organometallic Compounds from Organohalogen Compounds
14.10: Properties of Organometallic Compounds
14.11: Preparation of Organometallic Compounds
14.12: Organomagnesium Compounds
14.13: Organomagnesium and Organolithium Compounds in Synthesis
14.E: Organohalogen and Organometallic Compounds (Exercises)
15: Alcohols and Ethers
15.01: Prelude to Alcohols and Ethers
15.02: Physical Properties of Alcohols Hydrogen Bonding
15.03: Spectroscopic Properties of Alcohols
15.04: Preparation of Alcohols
15.05: Chemical Reactions of Alcohols. Reactions Involving the O-H Bond
15.06: Reactions Involving the C-O Bond of Alcohols
15.07: Oxidation of Alcohols
15.08: Polyhydric Alcohols
15.09: Unsaturated Alcohols - Alkenols
15.10: Protection of Hydroxyl Groups
15.11: Types and Reactions of Simple Ethers
15.12: Cyclic Ethers
15.E: Alcohols and Ethers (Exercises)
16: Carbonyl Compounds I- Aldehydes and Ketones. Addition Reactions of the Carbonyl Group
16.01: Prelude to Aldehydes and Ketones
16.02: The Carbonyl Bond
16.03: Physical Properties
16.04: Spectroscopic Properties
16.05: Typical Carbonyl-Addition Reactions
16.06: Catalytic Hydrogenation
16.07: Reduction of Carbonyl Compounds to Hydrocarbons
16.08: Oxidation of Carbonyl Compounds
16.09: Protection of Carbonyl Groups
16.10: Preparative Methods for Aldehydes and Ketones
16.11: General Methods for the Preparation of Aldehydes and Ketones
16.E: Carbonyl Compounds I (Exercises)
17: Carbonyl Compounds II- Enols and Enolate Anions. Unsaturated and Polycarbonyl Compounds
17.01: Prelude to Enols and Enolate Anions Unsaturated and Polycarbonyl Compounds
17.02: Enolization of Aldehydes and Ketones
17.03: Halogenation of Aldehydes and Ketones
17.04: Nucleophilic Addition Reactions of Enolate Anions
17.05: Nucleophilic Substitution with Enolate Anions
17.06: -Unsaturated Aldehydes and Ketones
17.07: Ketenes
17.08: 12-Dicarbonyl Compounds
17.09: 13-Dicarbonyl Compounds
17.10: 14-Dicarbonyl Compounds
17.11: Tricarbonyl Compounds
17.12: Cyclopropanones and Cyclopropenones
17.E: Carbonyl Compounds II (Exercises)
18: Carboxylic Acids and Their Derivatives
18.01: Prelude to Carboxylic Acids and Their Derivatives
18.02: Physical Properties of Carboxylic Acids
18.03: Some Chemical Properties of Carboxylic Acids
18.04: Reactions at the Carbonyl Carbon of Carboxylic Acids
18.05: Decarboxylation of Carboxylic Acids
18.06: Reactions at the (alpha) Carbons of Carboxylic Acids
18.07: Functional Derivatives of Carboxylic Acids
18.08: Reactions at the Carbonyl Carbon of Acid Derivatives
18.09: Reactions at the (alpha) Carbons of Carboxylic Acid Derivatives
18.10: Reactions of Unsaturated Carboxylic Acids and Their Derivatives
18.11: Dicarboxylic Acids
18.12: Methods of Preparation of Carboxylic Acids and Their Derivatives
18.E: Carboxylic Acids and Their Derivatives (Exercises)
19: More on Stereochemistry
19.01: Plane-Polarized Light and the Origin of Optical Rotation
19.02: Specific Rotation
19.03: Separation or Resolution of Enantiomers
19.04: Enantiomeric Purity
19.05: Absolute And Relative Configuration
19.06: The RS Convention for Designating Stereochemical Configurations
19.07: EZ Notation
19.08: Prochirality
19.09: Optical Rotatory Dispersion and Circular Dichroism
19.10: Asymmetric Synthesis
19.11: Racemization
19.E: More on Stereochemistry (Exercises)
20: Carbohydrates
20.01: Prelude to Carbohydrates
20.02: Classification and Occurrence of Carbohydrates
20.03: The Structure and Properties of D-Glucose
20.04: Conventions for Indicating Ring Size and Anomer Configurations of Monosaccharides
20.05: Derivatives of Glucose
20.06: Glycosides
20.07: Disaccharides
20.08: Polysaccharides
20.09: Vitamin C
20.10: Formation of Carbohydrates by Photosynthesis
20.11: The Generation of Energy from Carbohydrate Metabolism
20.E: Carbohydrates (Exercises)
21: Resonance and Molecular Orbital Methods
21.01: Prelude to Resonance and Molecular Orbital Methods
21.02: Characteristics of Simple Covalent Bonds
21.03: Comparison of the Resonance and Molecular-Orbital Methods
21.04: The Benzene Problem
21.05: Application of the MO Method to 13-Butadiene
21.06: Application of MO Theory to Other Systems
21.07: Which Is Better- MO or VB
21.08: More on Stabilization Energies
21.09: Bond Lengths and Double-Bond Character
21.10: Huckel's 4n 2 Rule
21.11: Pericyclic Reactions
21.12: Evidence Bearing on the Mechanism of 2 2 Cycloadditions
21.E: Resonance and Molecular Orbital Methods (Exercises)
22: Arenes Electrophilic Aromatic Substitution
22.01: Nomenclature of Arenes
22.02: Physical Properties of Arenes
22.03: Spectral Properties of Arenes
22.04: Electrophilic Aromatic Substitution
22.05: Effect of Substituents on Reactivity and Orientation in Electrophilic Aromatic Substitution
22.06: Orientation in Disubstituted Benzenes
22.07: IPSO Substitution
22.08: Substitution Reactions of Polynuclear Aromatic Hydrocarbons
22.09: Addition Reactions of Arenes
22.10: Oxidation Reactions
22.11: Sources and Uses of Aromatic Hydrocarbons
22.12: Some Conjugated Cyclic Polyenes
22.13: Fluxional Compounds
22.E: Arenes Electrophilic Aromatic Substitution (Exercises)
23: Organonitrogen Compounds I - Amines
23.01: Amines Compared with Alcohols
23.02: Naturally Occurring Amines
23.03: Types and Nomenclature of Amines
23.04: Physical Properties of Amines
23.05: Spectroscopic Properties of Amines
23.06: Stereochemistry of Amines
23.07: Amines as Bases
23.08: Amines as Acids
23.09: Amines as Nucleophiles
23.10: Amines with Nitrous Acid
23.11: Oxidation of Amines
23.12: Synthesis of Amines
23.13: Protection of Amino Groups in Synthesis
23.14: Carcinogenic Nitrogen Compounds
23.E: Organonitrogen Compounds I- Amines (Exercises)
24: Organonitrogen Compounds II - Amides Nitriles and Nitro Compounds
24.01: Structural Physical and Spectral Characteristics of Amides
24.02: Amides as Acids and Bases
24.03: Synthesis of Amides
24.04: Hydrolysis of Amides
24.05: Nitriles
24.06: Nitro Compounds
24.07: Some Compounds with N-N Bonds
24.E: Organonitrogen Compounds II- Amides Nitriles and Nitro Compounds (Exercises)
25: Amino Acids Peptides and Proteins
25.01: Types of Biologically Important Amino Acids
25.02: Acid-Base Properties of (alpha)-Amino Acids
25.03: Physical and Spectroscopic Properties
25.04: Analysis of Amino Acids
25.05: Reactions of Amino Acids
25.06: Synthesis of -Amino Acids
25.07: Peptides and Proteins
25.08: Structure and Function of Proteins
25.09: Enzymes
25.10: Coenzymes
25.11: Enzyme Regulation
25.12: Enzyme Technology
25.13: Biosynthesis of Proteins
25.14: Chemical Evolution
25.E: Amino Acids Peptides and Proteins (Exercises)
26: More on Aromatic Compounds
26.01: Aryl Oxygen Compounds
26.02: Quinones
26.03: Tropolones and Related Compounds
26.04: Some Aromatic Side-Chain Compounds
26.05: Natural Occurrence and Uses of Some Aromatic Side-Chain Compounds
26.06: Correlations of Structure with Reactivity of Aromatic Compounds
26.E: More on Aromatic Compounds (Exercises)
27: More about Spectroscopy
27.01: Prelude to More Spectroscopy
27.02: Line-Width Differences in NMR
27.03: Use of the Uncertainty Principle to Measure the Rates of Chemical Transformations
27.04: Why Spin-Spin Splitting
27.05: Chemically Induced Dynamic Nuclear Polarization (CIDNP)
27.06: Photoelectron Spectroscopy
27.07: Mossbauer Spectroscopy
27.08: Field- and Chemical-Ionization Mass Spectroscopy
27.09: Ion-Cyclotron Resonance
27.10: Electron-Spin Resonance (ESR) Spectroscopy of Organic Radicals
27.E: More about Spectroscopy (Exercises)
28: Photochemistry
28.01: Prelude to Photochemistry
28.02: Light Absorption Flourescence and Phosphorescence
28.03: Organic Photochemistry
28.04: Chemiluminescence
28.05: Color and Constitution
28.06: The Sensation of Color
28.07: Color Photography
28.08: Chemistry of Vision
28.E: Photochemistry (Exercises)
29: Polymers
29.01: Prelude
29.02: A Simple Addition Polymerization. The Parts of a Polymer
29.03: Types of Polymers
29.04: Forces Between Polymer Chains
29.05: Correlation of Polymer Properties with Structure
29.06: Condensation Polymers
29.07: Addition Polymers
29.08: Block Graft and Ladder Polymers
29.09: Naturally Occurring Polymers
29.10: Preparation of Synthetic Polymers
29.E: Polymers (Exercises)
30: Natural Products and Biosynthesis
30.01: Classification of Natural Products
30.02: Approaches to the Study of Natural Products
30.03: Isoprenoid Compounds
30.04: Steroids
30.05: Biosynthesis
30.06: Some Nitrogen-Containing Natural Products
30.07: Prostaglandins
30.E: Natural Products and Biosynthesis (Exercises)
31: Transition Metal Organic Compounds
31.01: Metallocenes
31.02: Other Organometallic Compounds of Transition Metals
31.03: Transition-Metal Compounds as Reagents for Organic Syntheses
31.04: Some Homogeneous Catalytic Reactions Involving Transition-Metal Complexes
31.05: -Propenyl Complexes of Nickel
31.06: Vitamin B as an Organometallic Compound
31.E: Transition Metal Organic Compounds (Exercises)