Chapter 24 Organic Compounds
In Chapter 2 "Molecules, Ions, and Chemical Formulas", you were introduced to the major classes of organic compounds, covalent compounds composed primarily of carbon and hydrogen. Organic substances have been used throughout this text to illustrate the differences between ionic and covalent bonding and to demonstrate the intimate connection between the structures of compounds and their chemical reactivity. You learned, for example, that even though NaOH and alcohols (ROH) both have OH in their formula, NaOH is an ionic compound that dissociates completely in water to produce a basic solution containing Na+ and OH− ions, whereas alcohols are covalent compounds that do not dissociate in water and instead form neutral aqueous solutions. You also learned that an amine (RNH2), with its lone pairs of electrons, is a base, whereas a carboxylic acid (RCO2H), with its dissociable proton, is an acid. (For more information on acids and bases, see Chapter 2 "Molecules, Ions, and Chemical Formulas", Section 2.5 "Acids and Bases".)
The structure of a solid with a hybrid metal-organic framework. Organic and inorganic groups of the proper structure can be used to synthesize solids with very large pores (central sphere) that can accommodate a variety of small molecules. The rigid benzene rings are used as “props” to hold the metal units (carboxylate-bridged copper dimers) apart. Such solids have potential applications in hydrogen storage for use in fuel cells or automobiles.
Carbon is unique among the elements in its ability to catenate, to form a wide variety of compounds that contain long chains and/or rings of carbon atoms. (For more information on carbon, see Chapter 12 "Solids", Section 12.8 "Polymeric Solids", and Chapter 22 "The ", Section 22.2 "The Elements of Group 14".) Some of the most complex chemical structures known are those of the organic molecules found in living organisms. (For more information on biopolymers, see Chapter 12 "Solids", Section 12.8 "Polymeric Solids".) In spite of their size and complexity, these biological molecules obey the same chemical principles as simpler organic molecules. Thus we can use Lewis electron structures to understand the preferred mode of reactivity of a variety of organic compounds, relative electronegativities and bond polarities to predict how certain groups of atoms will react, and molecular orbital theory to explain why certain organic species that contain multiple bonds are especially stable or undergo particular reactions when they interact with light. (For more information on Lewis electron structures, see Chapter 8 "Ionic versus Covalent Bonding", Section 8.5 "Lewis Structures and Covalent Bonding". For more information on bonding, see Chapter 8 "Ionic versus Covalent Bonding", Section 8.9 "Polar Covalent Bonds". For more information on light interactions, see Chapter 9 "Molecular Geometry and Covalent Bonding Models", Section 9.4 "Polyatomic Systems with Multiple Bonds".) In this chapter, we continue our description of organic compounds by focusing on their molecular structures and reactivity; we will also introduce some of the fundamental types of reactions and reaction mechanisms you will encounter in organic and biological chemistry. We discuss why butter is a solid and oils are liquids despite the apparent similarities in their structures, why the widely used anti-inflammatory drug ibuprofen takes longer than half an hour to relieve pain, and the identity of the major carcinogen in grilled meats and cigarette smoke. The chapter concludes with a brief introduction to the molecules of life, which will explain how the consumption of lactose can result in mental retardation and cirrhosis of the liver in some individuals, how hibernating animals survive during the winter, and how certain groups of antibiotics kill bacteria that are harmful to humans.