Welcome to organic chemistry! This text has been written for students. It emphasizes the practical details and skills needed to master this challenging subject. Learning organic chemistry is brain yoga! Our brains become strong and flexible with practice.
Because the first year of general chemistry covers such a wide range of topics, this chapter will briefly review some of the more relevant concepts for first year organic chemistry. If these basic concepts do NOT feel mastered, then refer to the general chemistry LibreTexts resources. This chapter will also build and expand on some topics with new information as organic chemistry is introduced.
In this chapter, we will apply theories of bonding and polarity to organic compounds to determine the intermolecular forces (IMFs) of organic molecules. To communicate about organic compounds, we need to be able to recognize, name, and distinguish between functional groups, so nomenclature and isomerism are introduced. All of this knowledge is integrated to predict solubility, relative boiling points, and relative densities.
This chapter introduces the concept of chirality and looks more closely at stereochemistry. The structures of compounds containing one or two chiral centers are emphasized and molecular modeling assists in the understanding of the phenomenon of chirality. Enzymes and receptors involve stereochemistry so this topic is important to both synthetic organic pathways and biochemistry.
This chapter introduces the mechanisms of organic reactions. Two types of reaction pathways are introduced—polar reactions and radical reactions. The chapter briefly reviews a number of topics from first year general chemistry including rates and equilibria, elementary thermodynamics and bond dissociation energies. A working knowledge of these topics is applied to the reaction mechanism for the free radical halogenation of alkanes.
Alkyl halides are electrophiles, which means they can undergo nucleophilic substitution and base-induced elimination reactions. These reaction types offer a large and useful range of reactions for organic synthesis in the laboratory. Alkyl halides are an o-chem student's best friend.
Understanding the bonding structure of alkenes helps explain their stereochemistry and how to synthesize them. In this chapter we will apply bonding theories to alkene structure and synthesis. Nomenclature of alkenes was introduced in Chapter 3 and is extended to the E/Z system in this chapter.
Addition reactions not only dominate the chemistry of alkenes, they are also the major class of reaction for alkynes. An important difference between (terminal) alkynes and alkenes is the acidity of the former. We have now learned enough reactions that we can begin devising multi-step organic syntheses. The nomenclature of alkynes is explained in chapter 3.
Alcohols are neither good nucleophiles , nor good electrophiles. Therefore, alcohols are chemically changed to increase their reactivity for either role. In the last chapter, we synthesized alcohols by reducing carbonyls. In this chapter, we will oxidize alcohols to produce carbonyls. The protecting group strategy for multi-step syntheses is introduced.
Alcohols can undergo a wide variety of reactions and can be prepared in a number of different ways. Alcohols are the first functional group capable of H-bonding that we are studying. This polarity can lead to full ionization in strongly basic environments of organic solvents. The physical properties of alcohols are discussed along with industrial scale applications and uses. The nomenclature of alcohols is explained in chapter 3.
The processes of identifying and characterizing organic compounds are of great importance to the working organic chemist. With the use of modern instrumental techniques, these tasks can now be accomplished much more readily than in the past. In this chapter, you will learn about two spectroscopic techniques (mass spectroscopy and infrared spectroscopy) that are used to identify organic compounds.
NMR is a non-destructive technique and has found uses in fields of medicine, chemistry, and environmental science. The two most common forms of NMR spectroscopy, ¹H NMR and ¹³C NMR, are discussed, the former in much more detail than the latter.
Ether synthesis and reactivity are discussed. However the relative inertness of ethers combined with their slight polarity makes ethers excellent solvents for many organic reactions. Crown ethers are discussed in their role as solvents, as well. Cyclic ethers containing a three‑membered ring, epoxides, are useful synthetic reagents and will be discussed in greater detail.
In this chapter, we study compounds that contain two carbon-carbon double bonds which are separated by one carbon-carbon single bond. These compounds are called “conjugated dienes.” Molecular orbital theory can help us understand the chemical reactivity of conjugated dienes.
While benzene is the primary aromatic compound, aromaticity can be present in larger hydrocarbons and heterocyclic compounds and can play a role in determining reaction intermediate stability. Aromaticity will defined more completely using the terms of resonance and molecular orbital theory. We will learn how to predict aromaticity using the Hückel (4n + 2) rule. The chapter concludes with a brief summary of the spectroscopic properties of arenes. Nomenclature of aromatic compounds was covered
Electrophilic aromatic substitution (EAS) reactions and their mechanisms are introduced. The factors that determine both the rate and position of substitution (regiochemistry) are explored in detail with an emphasis on synthetic strategies for multiple substitutions. Nucleophilic aromatic substitution reactions are also introduced with a discussion of the benzyne intermediate.
The acidity of carboxylic acids can be influenced by structural effects. The synthesis and reactivity of carboxylic acids is discussed. Carboxylic acids are important biochemically for both protein and lipid chemistry.
The reactions of carboxylic acid derivatives (acyl halides, acid anhydrides, esters and amides) and nitriles are explained. Structure elucidation from spectroscopy data is also discussed. Some biochemical significant compounds and reactions are introduced.
Amines are the first nitrogen-containing compounds that we study in detail in this text. The basicity of amines brings a new dynamic to their reactivity. The chemistry of amines plays an important role in biochemistry and pharmacology. Plants produce biologically active amines known as alkaloids.
This chapter provides an overview of the biologically important group of compounds known as carbohydrates. Many of the compounds you will encounter while studying this chapter may appear to have very complex structures, but much of their chemistry can be readily understood in terms of the concepts and reactions discussed in earlier chapters of the course.
Amino acids are important biochemicals, as they are the building blocks from which proteins and polypeptides are assembled. The fundamental chemistry of amino acids, peptides and proteins is discussed.
Lipids are naturally occurring organic compounds that can be extracted from cells and tissues using nonpolar solvents. Although many lipids have complex structures, their chemistry can often be understood quite readily by applying the basic concepts you have studied in previous units. We begin the unit with a study of fats and oils, and explain the different origins of these structurally similar substances.
Two types of nucleic acids are found in cells—deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). These highly complex substances are built up from a number of simpler units, called nucleotides. Each nucleotide consists of three parts: a phosphoric acid residue, a sugar and a nitrogen‑containing heterocyclic base. This chapter examines the structure and replication of DNA and then describes the structure and synthesis of RNA with a brief study of the role played by RNA in the biosynthesis of