This general organic Textmap by John D. Robert and Marjorie C. Caserio emphasizes thermochemistry to aid the undergraduate's understanding of organic reactions
• ## 1: Introduction to Organic Chemistry

You now are starting the study of organic chemistry, which is the chemistry of compounds of carbon. In this introductory chapter, we will tell you some- thing of the background and history of organic chemistry, something of the problems and the rewards involved, and something of our philosophy of what is important for you to learn so that you will have a reasonable working knowledge of the subject, whether you are just interested in chemistry or plan for a career as a chemist.
• ## 2: Structural Organic Chemistry

This chapter briefly reviews the most important types of covalent bonds encountered in organic substances and the ways in which these bonds are represented in structural formulas. Then it considers the sizes and shapes of organic molecules and how structural formulas written in two dimensions can be translated into three-dimensional models that show the relative positions of the atoms in space. We also discuss models that reflect the relative sizes of the atoms and may sterically interact.
• ## 3: Organic Nomenclature

A chemical nomenclature is a set of rules to generate systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Applied Chemistry (IUPAC). The primary function of chemical nomenclature is to ensure that a spoken or written chemical name leaves no ambiguity concerning which chemical compound the name refers to: each chemical name should refer to a single substance.
• ## 4: Alkanes

Alkanes are the simplest organic molecules, consisting of only carbon and hydrogen and with only single bonds between carbon atoms. Alkanes are used as the basis for naming the majority of organic compounds (their nomenclature). Alkanes have the general formula $$C_nH_{2n+2}$$.
• ## 5. Stereoisomerism of Organic Molecules

Position isomers wherein compounds of the same molecular formula differ because substituents, chain branches, and so on, are not at the same positions in the molecules. 1-Chloropropane & 2-chloropropane are straightforward examples of position isomers. A much more subtle form of isomerism is present when two different compounds have the same molecular formulas, the same substituent and chain-branching positions, and, indeed, even have the same names by all of the established nomenclature rules.
• ## 6: Bonding in Organic Molecules

Remembering that electrons and nuclei are charged particles, and that it is electrical forces of attraction and repulsion between the electrons and nuclei that determine the bonding. What we will try to do in this chapter is to show you how the modern electronic theory of chemical bonding provides strong support for the use of ball-and-stick models for many organic molecules, and also where it indicates that the models need to be modified or cannot properly represent the structural arrangements.
• ## 7: Other Compounds than Hydrocarbons

We begin our study of compounds with a range of functional groups other than hydrocarbons and consider the nomenclature of organic compounds of oxygen, nitrogen, and halogens. Many of the principles you have learned in connection with naming hydrocarbons will have direct application to these compounds. We will use systematic nomenclature to obtain first-choice names, but we also will indicate common usage, at least parenthetically.
• ## 8: Nucleophilic Substitution and Elimination Reactions

Nucleophilic substitution is a fundamental class of reactions in which an electron rich nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms to replace a so-called leaving group.
• ## 9: Separation, Purification, & Identification of Organic Compounds

Separations can be achieved by differences in physical properties, such as differences in boiling point, or by chemical means, wherein differences in physical properties are enhanced by chemical reactions. In this chapter we will consider some separations of compounds based on differences in physical properties. Chemical procedures will be discussed elsewhere in connection with the appropriate classes of compounds.
• ## 10: Alkenes and Alkynes I - Ionic and Radical Addition Reactions

With few exceptions, the multitude of reactions discussed in introductory texts are classified as ionic reactions. By this we mean that nucleophilic and electrophilic sites in reacting molecules bond to each other. Furthermore, charged species such as carbocations, carbanions, conjugate acids and conjugate bases are often intermediates on the reaction path, the overall transformation taking place in two or more discrete steps.
• ## 11: Alkenes and Alkynes II - Oxidation and Reduction Reactions. Acidity of Alkynes

Further chemistry of alkenes and alkynes is described in this chapter, with emphasis on addition reactions that lead to reduction and oxidation of carbon-carbon multiple bonds. First we explain what is meant by the terms reduction and oxidation as applied to carbon compounds. Then we emphasize hydrogenation, which is reduction through addition of hydrogen, and oxidative addition reactions.
• ## 12: Cycloalkanes, Cycloalkenes and Cycloalkynes

Cycloalkanes are hydrocarbons that contain rings of carbon atoms linked together by single bonds. They make up a particularly important homologous series in which the chemical properties change in a much more dramatic way than do those of the acyclic hydrocarbons. The cycloalkanes with small rings are of special interest in exhibiting chemical properties intermediate between those of alkanes and alkenes.
• ## 13: Polyfunctional Compounds, Alkadienes, and Approaches to Organic Synthesis

Organic compounds of natural origin rarely have simple structures. Most have more than one functional group in each molecule. Usually the chemical behavior of a functional group is influenced significantly by the presence of another functional group, especially when the groups are in close proximity. Indeed, the complexities that are associated with polyfunctionality are of central importance in biochemical reactions and in the design of organic syntheses.
• ## 14: Organohalogen & Organometallic Compounds

The general term of "organohalogen" refers to compounds with covalent carbon-halogen bonds. Substances such a bromomethane ($$\ce{CH_3Br}$$) and chloroethene ($$\ce{CH_2=CHCl}$$), are examples of organohalogen compounds, whereas others such as the methylammonium chloride salt, which have no carbon-halogen bonds, are not. This chapter is only concerned with compounds that have covalent carbon-halogen bonds.
• ## 15: Alcohols and Ethers

The physical, chemical and spectroscopic properties of alcohols are relative to it’s chemical structures. Alcohols are compounds of the general formula ROH, where R is any alkyl or substituted alkyl group. The simple ethers, ROR, do not have O-H bonds, and most of their reactions are limited to the substituent groups.
• ## 16: Carbonyl Compounds I: Aldehydes and Ketones. Addition Reactions of the Carbonyl Group

It is convenient to discuss aldehydes and ketones separately from carboxylic acids and, following some general observations about the carbonyl group, this chapter mainly is concerned with aldehydes and ketones.
• ## 17: Carbonyl Compounds II: Enols and Enolate Anions. Unsaturated and Polycarbonyl Compounds

Some of the most useful reactions of carbonyl compounds involve carbon-hydrogen bonds adjacent to the carbonyl group. Such reactions, which can be regarded as the backbone of much synthetic organic chemistry, usually result in the replacement of the hydrogen by some other atom or group. The important examples we will consider in this chapter are halogenation, alkylation, and aldol reactions of aldehydes and ketones.
• ## 18: Carboxylic Acids and Their Derivatives

Now we will be concerned mostly with putting concepts together, moving from the simple to the complex. For example, in this chapter we will be trying to understand the ways that carboxylic acids, which possess the −COOH functional group, are similar to and different from alcohols, which have the −OH group, and aldehydes and ketones, which have C=O bonds.
• ## 19: More on Stereochemistry

There are, however, practical aspects of stereochemistry that have not yet been mentioned, particularly with regard to chiral compounds. How, for instance, can a racemic mixture be separated into its component enantiomers (resolution); what methods can be used to establish the configuration of enantiomers; how can we tell if they are pure; and how do we synthesize one of a pair of enantiomers preferentially (asymmetric synthesis)?
• ## 20: Carbohydrates

Carbohydrates are a major class of naturally occurring organic compounds, which come by their name because they usually have, or approximate, the general formula Cn(H2O)m , with nn equal to or greater than three. Among the well-known carbohydrates are various sugars, starches, and cellulose, all of which are important for the maintenance of life in both plants and animals.
• ## 21: Resonance and Molecular Orbital Methods

Molecular orbital theory is a method for determining molecular structure in which electrons are not assigned to individual bonds between atoms, but are treated as moving under the influence of the nuclei in the whole molecule. The spatial and energetic properties of electrons within atoms are fixed by quantum mechanics to form orbitals that contain these electrons.
• ## 22: Arenes, Electrophilic Aromatic Substitution

Benzene and other aromatic hydrocarbons usually have such strikingly different properties from typical open-chain conjugated polyenes, such as 1,3,5-hexatriene, that it is convenient to consider them as a separate class of compounds called arenes. In this chapter we shall outline the essential features of the chemistry of arenes, particularly their reactions with electrophilic reagents which result in the substitution of a ring hydrogen with other functional groups
• ## 23: Organonitrogen Compounds I: Amines

A wide variety of organic compounds contain nitrogen. In fact, the types of nitrogen compounds are so numerous and diverse that we shall be unable to consider them all. We shall give most attention to the chemistry of amines and amides in this and the following chapter, because these represent the two largest classes of nitrogen compounds.
• ## 24: Organonitrogen Compounds II: Amides, Nitriles, & Nitro Compounds

The properties of the simple amides are relevant to the chemistry of peptides and proteins, substances that are fundamental to all life as we know it. Indeed, the characteristics of peptides and proteins are primarily due to their polyamide structures. For this reason, it is important to know and understand the chemistry of simple amides.
• ## 25: Amino Acids, Peptides, and Proteins

The chemistry of life is largely the chemistry of polyfunctional organic compounds. The functional groups usually are of types that interact rather strongly as, for example, the hydroxyl and carbonyl functions of carbohydrates. The interaction between amino and carboxyl functions of amino acids figures greatly in the present chapter. We will approach the very important chemistry of amino acids and their derivatives in three stages.
• ## 26: More on Aromatic Compounds

the reactivity of a substituent on an aromatic ring is greatly modified from that of its aliphatic counterpart. Likewise, the substituent can influence the reactivity of the ring. We have seen this interplay between ring and substituent in the chemistry of aryl halides, of arenamines, and in electrophilic substitution reactions of aromatic compounds. It is particularly manifest in the chemistry of substances that have oxygen attached directly to arene rings.
• ## 27: More about Spectroscopy

Previously, in NMR spectra, we passed rather quickly over the basis of understanding why some lines are broad and others sharp, why rate effects can cause chemical shifts to be averaged, and how to correlate spin-spin splitting with the energies of NMR transitions. These topics will be discussed in this chapter along with a brief explanation of the remarkable effects on NMR spectra associated with some kinds of chemical reactions, namely, chemically induced dynamic nuclear polarization (CIDNP)
• ## 28: Photochemistry

Quite  apart  from  the  unparalleled  importance  of  photosynthesis, photo-chemical reactions  have  a great  impact on  biology  and technology,  both  good  and  bad.  Vision  in  all  animals  is  triggered  by  photochemical  reactions.  The  destructive  effects  of  ultraviolet radiation on  all  forms  of  life  can be traced  to  photochemical  reactions  that  alter  cellular  DNA,  and  the  harmful  effects  of  overexposure  to  sunlight  are  well  established.
• ## 29: Polymers

Polymers are substances made up of recurring structural units, each of which can be regarded as derived from a specific compound called a monomer. The number of monomeric units usually is large and variable, each sample of a given polymer being characteristically a mixture of molecules with different molecular weights. The range of molecular weights is sometimes quite narrow, but is more often very broad.
• ## 30: Natural Products and Biosynthesis

Natural products are compounds that are produced by a living organism. This definition encompasses many compounds already discussed, such as carbohydrates, proteins, lipids, and nucleic acids, all of which play an important and primary role in metabolic reactions. However, there are other organic compounds produced naturally, some of extraordinary complexity, which are not primary metabolites.
• ## 31: Transition Metal Organic Compounds

The discovery of ferrocene in 1951 by P. L. Pauson was revolutionary. Ferrocene has unheard of properties for an organoiron compound, stable to more than 500° and able to be dissolved in, and recovered from, concentrated sulfuric acid! Pauson's work started an avalanche of research on transition metals in the general area between organic and inorganic chemistry, which has flourished ever since and has led to an improved understanding of important biochemical processes.