PART 1. GENERAL ASPECTS OF CHEMICAL STRUCTURE AND REACTIVITY OF ORGANIC COMPOUNDS
CHAPTER 1. CHEMICAL STRUCTURE AND BONDING
1.1. The Structural Theory of Organic Compounds
1.2. The Structure of Atoms
1.2.1. Atomic Orbitals
1.2.2. Electronic Configuration
1.3. The Nature of Chemical Bonding
1.3.1. Ionic Bonds
1.3.2. Covalent Bonds
1.4. Bonding in Carbon Compounds
1.4.1. sp3 Hybridization
1.4.2. sp2 Hybridization
1.4.3. sp Hybridization
1.4.4. Hybridization of Other Atoms
1.5. The Representation of Structural Formulas
1.6. Shape of Molecules and Molecular Models
Additional Problems
СHAPTER 2. CLASSIFICATION AND NOMENCLATURE OF ORGANIC COMPOUNDS
2.1. Classification
2.1.1. Classification According to the Molecular Framework
2.1.2. Classification According to Functional Groups
2.2. Nomenclature
2.2.1. General Principles of the IUPAC Nomenclature
2.2.2. General Principles of Forming a Systematic Name
2.2.3. Names of Parent Structures
2.2.4. Examples of Constructing the Systematic Names
Additional Problems
CHAPTER 3. ELECTRONIC STRUCTURE OF ORGANIC MOLECULES
3.1. Conjugation as Stabilizing Factor of Molecules
3.1.1. Conjugation
3.1.2. p. Conjugation
3.2. Aromaticity
3.2.1. Benzene
3.2.2. Modern Theories of the Structure of Benzene
3.3. Electronic Effects in Organic Molecules
3.3.1. Polar and Nonpolar Covalent Bonds
3.3.2. Inductive Effect
3.3.3. Mesomeric Effect
Additional Problems
CHAPTER 4. A BRIEF SURVEY OF ORGANIC REACTIONS
4.1. Types of Organic Reactions
4.2. Reaction Mechanisms
4.2.1. Radical and Polar Processes
4.2.2. Types of Reagents
4.3. Energetics of Chemical Reactions
4.3.1. Activation Energy and Reaction Energy Diagram
4.3.2. Catalysis
Additional Problems
CHAPTER 5. ACIDITY AND BASICITY OF ORGANIC COMPOUNDS
5.1. General Concepts of Acids and Bases
5.2. Acids
5.2.1. Electronegativity and Polarizability of an Atom
5.2.2. Delocalization of a Charge in an Anion
5.2.3. Solvation Effects
5.3. Bases
5.4. Acidic and Basic Sites in a Molecule
Additional Problems
CHAPTER 6. HYDROCARBONS
6.1. Classification
6.2. Saturated Hydrocarbons
6.2.1. Conformational Isomerism
6.2.2. Chemical Properties
6.2.3. Cyclopropane
6.3. Unsaturated Aliphatic Hydrocarbons
6.3.1. Isomerism
6.3.2. Addition Reactions of Alkenes
6.3.3. Addition Reactions to Dienes
6.4. Aromatic Hydrocarbons
6.4.1. Electrophilic Aromatic Substitution
6.4.2. Substituent Effects in Electrophilic Aromatic Substitution
6.4.3. Oxidation and Reduction of Arenes
Additional Problems
PART 2. MONOFUNCTIONAL ORGANIC COMPOUNDS OF BIOLOGICAL INTERESTS
CHAPTER 7. ORGANIC HALIDES, ALCOHOLS, PHENOLS, ETHERS, AMINES, AND ORGANOSULFUR COMPOUNDS
7.1. Organic Halides
7.1.1. Nucleophilic Substitution Reactions
7.1.2. Elimination Reactions
7.2. Alcohols, Phenols, and Thiols
7.2.1. Classification and Nomenclature
7.2.2. Acidic and Basic Properties
7.2.3. Electrophilic and Nucleophilic Properties
7.2.4. Elimination Reactions
7.2.5. Oxidation Reactions
7.3. Ethers and Sulfides
7.4. Amines
7.4.1. Classification and Nomenclature
7.4.2. Chemical Properties
7.5. Biochemical Alkylations
Additional Problems
CHAPTER 8. CARBONYL COMPOUNDS
8.1. General Characteristics of Aldehydes and Ketones
8.1.1. Classification and Nomenclature
8.1.2. Electronic Structure of the Carbonyl Group
8.2. Nucleophilic Addition Reactions
8.2.1. Addition of Alcohols: Hemiacetal and Acetal Formation
8.2.2. Addition of Water: Hydration
8.2.3. Addition of Nitrogen Nucleophiles: Imines and Related Compounds
8.3. CH-Acidic Properties of Aldehydes and Ketones
8.3.1. Keto-Enol Tautomerism
8.3.2. The Aldol Condensation
8.3.3. The Biochemical Aldol Condensation
8.3.4. The Haloform Reaction
8.4. Oxidation and Reduction Reactions
8.4.1. Oxidation of Aldehydes and Ketones
8.4.2. Reduction of Aldehydes and Ketones
8.4.3. Biochemical Oxidation and Reduction of Carbonyl Compounds
Additional Problems
CHAPTER 9. CARBOXYLIC ACIDS AND THEIR DERIVATIVES
9.1. General Characteristics of Carboxylic Acids
9.1.1. Classification and Nomenclature
9.1.2. Electronic Structure of the Carboxyl Group
9.2. Acidic Properties
9.3. Nucleophilic Substitution at Acyl Carbon
9.3.1. Esterification of Carboxylic Acids
9.3.2. Acylation Reactions with Carboxylic Acid Derivatives
9.4. Ester Condensation
9.5. Decarboxylation of Carboxylic Acids
Additional Problems
PART 3. POLY- AND HETEROFUNCTIONAL COMPOUNDS IN LIVING SYSTEMS
CHAPTER 10. STEREOISOMERISM
10.1. Chiral and Achiral Objects
10.2. Optical Activity
10.3. Enantiomers
10.4. Configuration and the D,L Convention
10.5. Configuration and the R,S Convention
10.6. Molecules with More than One Chiral Centre
10.7. meso Compounds
10.8. Cis-trans isomerism
Additional Problems
CHAPTER 11. POLY- AND HETEROFUNCTIONAL COMPOUNDS
11.1. Types of Heterofunctional Compounds
11.2. Interaction of Different Groups in Heterofunctional Compounds
11.2.1. Intramolecular Reactions
11.2.2. Intermolecular Reactions
11.3. CH-Acidic Properties of Heterofunctional Compounds
11.3.1. Elimination Reactions
11.3.2. Keto-Enol Tautomerism
11.4. Decarboxylation of Heterofunctional Carboxylic Acids
11.5. Heterofunctional Compounds in Chemotherapy
11.5.1. Derivatives of Amino Alcohols and Amino Phenols
11.5.2. Derivatives of Amino Acids
11.5.3. Derivatives of Salicylic Acid
11.5.4. Derivatives of Sulfanilic Acid (Sulfa Drugs)
Additional Problems
CHAPTER 12. LIPIDS
12.1. Classification
12.2. Structural Components of Lipids
12.2.1. Fatty Acids
12.2.2. Alcohols
12.3. Simple Lipids
12.3.1. Waxes
12.3.2. Fats and Oils
12.3.3. Soaps and Detergents
12.4. Complex Lipids
12.4.1. Phospholipids
12.4.2. Glycolipids
Additional Problems
CHAPTER 13. TERPENOIDS AND STEROIDS
13.1. Terpenoids
13.2. Steroids
13.1.1. Structure of Steroids
13.2.2. Steroid Groups
13.2.3. General Chemical Characteristic of Steroids
Additional Problems
PART 4. BIOPOLYMERS AND THEIR STRUCTURAL CONSTITUENTS
CHAPTER 14. CARBOHYDRATES
14.1. Monosaccharides
14.1.1. Classification, Stereoisomerism, and Nomenclature
14.1.2. The Cyclic Hemiacetal Structures
14.1.3. Chemical Properties
14.2. Oligosaccharides
14.2.1. Reducing Disaccharides
14.2.2. Nonreducing Disaccharides
14.2.3. Chemical Properties
14.3. Polysaccharides
14.3.1. Homopolysaccharides
14.3.2. Heteropolysaccharides
14.4. Carbohydrates on Cell Surfaces
Additional Problems
CHAPTER 15. AMINO ACIDS, PEPTIDES, AND PROTEINS
15.1. Amino Acids
15.1.1. Structure and Classification
15.1.2. Chemical Properties
15.1.3. Biologically Important Reactions
15.2. Peptides and Proteins
15.2.1. Primary Structure
15.2.2. Secondary Structure
15.2.3. Tertiary Structure
15.2.4. Hydrolysis of Peptides and Proteins
Additional Problems
CHAPTER 16. BIOLOGICALLY ACTIVE HETEROCYCLIC COMPOUNDS
16.1. General Characteristics of Heterocyclic Systems
16.1.1. Classification
16.1.2. Nomenclature
16.2. General Aspects of Reactivity of Aromatic Heterocycles
16.2.1. Aromaticity of Pyridine and Pyrrole
16.2.2. Basicity and Acidity
16.2.3. Substitution Reactions in Heterocycles
16.3. Five-Membered Rings with One Nitrogen
16.4. Six-Membered Rings with One Heteroatom
16.4.1. Nitrogen-Containing Heterocycles
16.4.2. Oxygen-Containing Heterocycles
16.5. Rings with More than One Heteroatom
16.5.1. Imidazole and Pyrazole
16.5.2. Pyrimidine Derivatives
16.5.3. Purine Derivatives
16.6. Alkaloids
16.6.1. Pyridine Alkaloids
16.6.2. Quinoline and Isoquinoline Alkaloids
16.6.3. Tropane Alkaloids
Additional Problems
CHAPTER 17. NUCLEOTIDES AND NUCLEIC ACIDS
17.1. Constituents of Nucleic Acids
17.1.1. Structure of Nucleosides and Nucleotides
17.1.2. Some Chemical Properties of Nucleosides and Nucleotides
17.2. Primary Structure of Nucleic Acids
17.3. Secondary Structure of Nucleic Acids
17.4. Nucleoside Phosphates in Biological Processes
17.4.1. Nucleoside Polyphosphates
17.4.2. Nucleotide Coenzymes
Additional Problems
Appendix 1. PRINCIPAL PARAMETERS OF COVALENT BONDS
Appendix 2. GLOSSARY
Appendix 3. ANSWERS TO PROBLEMS
References
Subject Index