ASCOT Library Zabali Campus

1 Introduction – review of bond types and bond formation –
1.1 The electrovalent bond –
1.2 The covalent bond –
1.3 Dative covalency –
1.4 Partial ionic character of covalent bonds –
1.5 Electronegativity –
1.6 Molecular polarity –
1.7 Bond polarity and bond energy; bond length –
1.8 Organic and inorganic compounds –
2. Atomatic and molecular structures –
2.1. Atomic orbitals –
2.2 Molecular orbitals-orbital picture of covalent bonds –
2.3 Electronic configuration of some elements found in organic compounds –
2.4 Hybrid orbitals –
2.5 Hybridization of carbon atom –
2.6 Comparison of the bond lengths and bond energies of C-C bonds –
2.7 Delocalized chemical bonding –
2.8 Kinds of molecules which have delocalized bonds –
2.9 Resonance method in delocalized bonds –
2.10 Resonance energy –
2.11 Some common functional groups –
3. Organic reactions –
Characteristics of organic reactions –
3.1 Classes of organic reactions –
3.2 Reaction mechanism –
3.3 Reaction intermediates –
3.4 Hyperconjugation - relative stability of carbonium ions and free radicals –
3.5 The nature of organic reactions –
Energy relations in organic reactions –
3.6 Equilibrium –
3.7 Heat of reaction –
3.8 Free-energy diagram –
3.9 Rate of reaction –
3.10 Multistage reactions –
3.11 Competing reactions –
4. The aliphatic hydrocarbons – Acyclic and cyclic –
4.1 Hydrocarbons –
4.2 Sources and uses of hydrocarbons –
4.3 Homologous series –
4.4 Structural isomerism –
4.5 Alkyl groups –
4.6 Nomenclature –
4.7 Structure of aliphatic and alicyclic hydrocarbons –
4.71 Rotation about single bonds –
4.72 Restricted rotation about double bonds –
4.73 Restricted rotation in ring compounds –
4.8 Structure and physical properties –
4.9 Reactions –
4.91 Combustion –
4.92 Relative acidity of carbon to hydrogen bond –
4.93 Reactions of alkenes and cycloalkanes –
4.94 Reactions of alkenes and alkynes –
1. Hydrogenation –
2. Electrophilic addition –
3. Radical addition –
4. Multiple bond oxidation –
4.95 Reactions in petroleum refining –
5. Aromatic hydrocarbons –
5.1 Aromatic structure –
5.2 Nomenclature of aromatic hydrocarbons –
5.3 Physical properties and structure –
5.4 Reactions of aromatic hydrocarbons –
5.41 Addition to aromatic compounds –
5.42 Electrophilic aromatic substitution –
5.5 Electrophilic reagents –
5.51 Halogenation –
5.52 Nitration --
5.53 Sulfonation –
5.54 Friedel-Crafts alkylation –
5.55 Friedel-Crafts acylation –
5.6 Substituent effect on electrophilic substitution –
5.7 Explanations of orientation and reactivity –
5.71 Resonance effect –
5.72 Inductive effect –
5.73 Stability of the ground state structure –
5.74 Stability of the sigma complex –
6. Organic halides –
6.1 Introduction –
6.2 Classification and nomenclature –
6.3 Physical properties of organic halides –
Reactions of alkyl halides with a nucleophile –
6.4 Nucleophilic substitution in alkyl halides –
6.41 Stereochemical and kinetic course of substitution reaction –
6.42 Relative reactivity in substitution reactions –
6.43 Comparison between SN1 and SN2 reactions –
6.5 Nucleophilic substitution in aryl halides –
6.6 Nucleophilic elimination reactions –
6.61 Competing reaction of SN2 : E2 reaction –
6.62 Competing reaction of SN1 : E1 reaction –
6.7 Substitution and elimination reactions of alkyl halides –
6.71 Reaction with alkoxides and hydroxides –
6.72 Reaction with alcohols and water –
6.73 Reaction with cyanide –
6.74 Reaction with ammonia and amines –
6.75 Reaction with acetylides –
6.8 Reaction of Vic-Dihalides –
6.9 The Grignard reagent - an organometallic compound –
6.91 Other organomettalic compounds –
7. Alcohols, phenols and ethers –
7.1 Introduction –
7.2 Alcohols, phenols and ethers of commercial importance –
7.3 Structure and physical properties –
7.4 Acidity of alcohols, phenols and ethers –
7.5 Reactivity of alcohols, phenols and ethers –
7.6 Reactions of alcohols, phenols and ethers –
7.61 Reaction with halogen acids –
7.62 Reaction with concentrated strong acids –
7.63 Reaction with carbonyl compounds –
7.64 Reaction with oxiding agents –
8. Aldehydes and ketones –
8.1 Introduction –
8.2 Tautomerism –
8.3 Structure of the carbonyl group –
8.4 Structure and physical properties –
8.5 Reactivity and carbonyl group –
8.6 Nucleophilic additions to the carbonyl group –
8.7 Oxidation –
8.8 Reduction –
8.9 Halogenation and the haloform reaction –
8.10 Aldol condensation –
8.11 Cannizzaro reaction –
9. The carboxylic acids and their derivatives –
9.1 Introduction –
9.2 Sources and uses of organic acids –
9.3 Structure and physical properties –
9.4 Acidity of the carboxylic acids –
9.5 Reactions of carboxylic acids –
9.6 Salts of organic acids –
9.7 The carboxylic acid derivatives –
9.8 Reactions of acid derivatives –
9.9 Relative reactivities of the acid derivatives –
9.10 Reaction diagrams of the acid derivatives –
9.11 Qualitative tests –
9.12 Natural esters –
9.13 The hydroxy acids –
9.14 Optical isomerism –
9.15 Relative and absolute configuration –
10. Amines and diazonium compounds –
10.1 Introduction –
10.2 Sources of amines –
10.3 Structure and physical properties of amines –
10.4 Basicity of amines –
10.5 Reactions of amines –
10.51 Basic reactions –
10.52 Alkylation and Hofmann degradation –
10.53 Acylation –
10.54 Hinsberg reaction –
10.55 Reactions with nitrous acid –
10.56 Isocyanide test –
10.57 Oxidation –
10.6 Reactions of the aromatic diazonium salts –
10.61 Substitution –
10.62 The coupling reaction –
11. Carbohydrates –
11.1 Introduction –
11.2 Nomenclature and classification –
11.3 Stereoisomerism and configuration –
11.4 Structure of the monosaccharides –
11.5 Mutarotation –
11.6 Selected reactions of the monosaccharides –
11.61 Osazone formation –
11.62 Reaction with alkali –
11.63 Oxidation –
11.64 Interconversions of aldoses –
11.65 Action of strong acids –
11.66 Ester formation –
11.7 Glycosides –
11.8 Disaccharides –
11.81 Maltose –
11.82 Collobiose –
11.83 Lactose –
11.84 Sucrose –
11.9 Polysaccharides –
11.91 Starch –
11.92 Glycogen –
11.93 Cellulose –
11.94 Other polysaccharides –
12. Amino acids and properties –
12.1 Introduction –
12.2 Structure and configuration of amino acids –
12.3 Properties of amino acids –
12.31 Acid and base properties –
12.32 The isoelectric point –
12.4 Chemical reactions of amino acids –
12.41 Ester and amide formation –
12.42 Reaction with nitrous acid –
12.43 The Ninhydrin reaction –
12.44 Other color reactions –
12.5 Synthesis of amino acids –
12.6 Structure of proteins –
12.61 Classification –
12.7 Properties of proteins.

"The first edition of this text was written as a response to the need of those students taking a basic course in Organic Chemistry. The primary goal was to present a book which would be easy for the students to read and understand.
The general design of the first edition is retained in this second edition, that of following an electronic-mechanistic approach in treating the chemical properties of the organic compounds while keeping the systematic-classic or traditional functional group organization.
This second edition retains the emphasis on the best features of the present-day modern theories; the stress or orbital structures of organic molecules; the recognition of reactive sites; the use of energy profiles, transition states, stable and unstable intermediates for describing the courses of organic reactions; the involvement of the stereo-chemical aspects of these reactions to provide clear pictures of the mechanisms of the reactions and a discussion of the structural effects e.g. resonance, inductive effect, etc., which determine the rates and equilibria of reactions.
The authors have again chosen to omit discussions of the more sophisticated instrumental methods like infrared absorption, mass spectronomy, nuclear magnetic resonance, etc., because we do believe that students taking up a basic course in Organic Chemistry will not have the opportunity to make use of these techniques in the laboratory and the authors therefore reiterate that they depend on the individual teacher to supplement whatever particulars will be suitable for his class.
The second edition continues to be a text written for those students taking up a one year basic course in Organic Chemistry. By leaving out the details on kinetics, mechanisms, etc., the text may be used for a one semester course in Organic Chemistry. For this one semester course, the teacher may elect to assign the students to read the more descriptive portions of the chapters for a fuller coverage of the topics.
Once again we state that users of this text will find that a mastery of the first theoretical chapters will help provide them with self-confidence and a good foundation for learning the later chapters. The chapters on the amino acids, proteins and carbohydrates will be useful "stepping stones" for the field of biochemistry.
Lastly, because a book is never a "private project", the authors welcome criticisms, comments, corrections and suggestions so that errors, misprints, improvements, etc. that may have been missed in the revision of this text can be corrected in subsequent printings.” - The Authors