PREFACE
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
1.3. The Nature of Chemical Bonding
1.4. Bonding in Carbon Compounds
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
2.2. Nomenclature
Additional Problems
CHAPTER 3. ELECTRONIC STRUCTURE OF ORGANIC MOLECULES
3.1. Conjugation as Stabilizing Factor of Molecules
3.2. Aromaticity
3.3. Electronic Effects in Organic Molecules
Additional Problems
CHAPTER 4. A BRIEF SURVEY OF ORGANIC REACTIONS
4.1. Types of Organic Reactions
4.2. Reaction Mechanisms
4.3. Energetics of Chemical Reactions
Additional Problems
CHAPTER 5. ACIDITY AND BASICITY OF ORGANIC COMPOUNDS
5.1. General Concepts of Acids and Bases
5.2. Acids
5.3. Bases
5.4. Acidic and Basic Sites in a Molecule
Additional Problems
CHAPTER 6. HYDROCARBONS
6.1. Classification
6.2. Saturated Hydrocarbons
6.3. Unsaturated Aliphatic Hydrocarbons
6.4. Aromatic Hydrocarbons
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
7.2. Alcohols, Phenols, and Thiols
7.3. Ethers and Sulfides
7.4. Amines
7.5. Biochemical Alkylations
Additional Problems
CHAPTER 8. CARBONYL COMPOUNDS
8.1. General Characteristics of Aldehydes and Ketones
8.2. Nucleophilic Addition Reactions
8.3. CH-Acidic Properties of Aldehydes and Ketones
8.4. Oxidation and Reduction Reactions
Additional Problems
CHAPTER 9. CARBOXYLIC ACIDS AND THEIR DERIVATIVES
9.1. General Characteristics of Carboxylic Acids
9.2. Acidic Properties
9.3. Nucleophilic Substitution at Acyl Carbon
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
11.3. CH-Acidic Properties of Heterofunctional Compounds
11.4. Decarboxylation of Heterofunctional Carboxylic Acids
11.5. Heterofunctional Compounds in Chemotherapy
Additional Problems
CHAPTER 12. LIPIDS
12.1. Classification
12.2. Structural Components of Lipids
12.3. Simple Lipids
12.4. Complex Lipids
Additional Problems
CHAPTER 13. TERPENOIDS AND STEROIDS
13.1. Terpenoids
13.2. Steroids
Additional Problems
PART 4. BIOPOLYMERS AND THEIR STRUCTURAL CONSTITUENTS
CHAPTER 14. CARBOHYDRATES
14.1. Monosaccharides
14.2. Oligosaccharides
14.3. Polysaccharides
14.4. Carbohydrates on Cell Surfaces
Additional Problems
CHAPTER 15. α-AMINO ACIDS. PEPTIDES, AND PROTEINS
15.1. α-Amino Acids
15.2. Peptides and Proteins
Additional Problems
CHAPTER 16. BIOLOGICALLY ACTIVE HETEROCYCLIC COMPOUNDS
16.1. General Characteristics of Heterocyclic Systems
16.2. General Aspects of Reactivity of Aromatic Heterocycles
16.3. Five-Membered Rings with One Nitrogen
16.4. Six-Membered Rings with One Heteroatom
16.5. Rings with More than One Heteroatom
16.6. Alkaloids
Additional Problems
CHAPTER 17. NUCLEOTIDES AND NUCLEIC ACIDS
17.1. Constituents of Nucleic Acids
17.2. Primary Structure of Nucleic Acids
17.3. Secondary Structure of Nucleic Acids
17.4. Nucleoside Phosphates in Biological Processes
Additional Problems
Appendix 1. PRINCIPAL PARAMETERS OF COVALENT BONDS
Appendix 2. GLOSSARY
Appendix 3. ANSWERS TO PROBLEMS
References
Subject Index