Essential Organic Chemistry Second Edition

Book Preface

To stay alive, early humans must have been able to tell the difference between two kinds of materials in their world. “You can live on roots and berries,” they might have said, “but you can’t live on dirt. You can stay warm by burning tree branches, but you can’t burn rocks.” By the early eighteenth century, scientists thought they had grasped the nature of that difference. Compounds derived from living sources were believed to contain an unmeasurable vital force—the essence of life. Because they came from organisms, they were called “organic” compounds. Compounds derived from minerals—those lacking that vital force—were “inorganic.” Because chemists could not create life in the laboratory, they assumed they could not create compounds that had a vital force. Since this was their mind-set, you can imagine how surprised chemists were in 1828 when Friedrich Wöhler produced urea—a compound known to be excreted by mammals—by heating ammonium cyanate, an inorganic mineral.

For the first time, an “organic” compound had been obtained from something other than a living organism and certainly without the aid of any kind of vital force. Clearly, chemists needed a new definition for “organic compounds.” Organic compounds are now defined as compounds that contain carbon. Why is an entire branch of chemistry devoted to the study of carbon-containing compounds? We study organic chemistry because just about all of the molecules that make life possible—proteins, enzymes, vitamins, lipids, carbohydrates, and nucleic acids—contain carbon; thus, the chemical reactions that take place in living systems, including our own bodies, are reactions of organic compounds. Most of the compounds found in nature—those we rely on for food, medicine, clothing (cotton, wool, silk), and energy (natural gas, petroleum)—are organic compounds as well. Organic compounds are not, however, limited to those found in nature. Chemists have learned to synthesize millions of organic compounds never found in nature, including synthetic fabrics, plastics, synthetic rubber, medicines, and even things like photographic film and Super Glue.

Many of these synthetic compounds prevent shortages of naturally occurring products. For example, it has been estimated that if synthetic materials were not available for clothing, all of the arable land in the United States would have to be used for the production of cotton and wool just to provide enough material to clothe us. Currently, there are about 16 million known organic compounds, and many more are possible. What makes carbon so special? Why are there so many carbon-containing compounds? The answer lies in carbon’s position in the periodic table. Carbon is in the center of the second row of elements. The atoms to the left of carbon have a tendency to give up electrons, whereas the atoms to the right have a tendency to accept electron

Because carbon is in the middle, it neither readily gives up nor readily accepts electrons. Instead, it shares electrons. Carbon can share electrons with several different kinds of atoms, and it can also share electrons with other carbon atoms. Consequently, carbon is able to form millions of stable compounds with a wide range of chemical properties simply by sharing electrons. When we study organic chemistry, we study how organic compounds react. When an organic compound reacts, some existing bonds break and some new bonds form. Bonds form when two atoms share electrons, and bonds break when two atoms no longer share electrons.

How readily a bond forms and how easily it breaks depend on the particular electrons that are shared, which, in turn, depend on the atoms to which the electrons belong. So if we are going to start our study of organic chemistry at the beginning, we must start with an understanding of the structure of an atom—what electrons an atom has and where they are located.