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Chapter 13 Unsaturated and Aromatic Hydrocarbons

Opening Essay

Our modern society is based to a large degree on the chemicals we discuss in this chapter. Most are made from petroleum. In Chapter 12 "Organic Chemistry: Alkanes and Halogenated Hydrocarbons" we noted that alkanes—saturated hydrocarbons—have relatively few important chemical properties other than that they undergo combustion and react with halogens. Unsaturated hydrocarbons—hydrocarbons with double or triple bonds—on the other hand, are quite reactive. In fact, they serve as building blocks for many familiar plastics—polyethylene, vinyl plastics, acrylics—and other important synthetic materials (e.g., alcohols, antifreeze, and detergents). Aromatic hydrocarbons have formulas that can be drawn as cyclic alkenes, making them appear unsaturated, but their structure and properties are generally quite different, so they are not considered to be alkenes. Aromatic compounds serve as the basis for many drugs, antiseptics, explosives, solvents, and plastics (e.g., polyesters and polystyrene).

The two simplest unsaturated compounds—ethylene (ethene) and acetylene (ethyne)—were once used as anesthetics and were introduced to the medical field in 1924. However, it was discovered that acetylene forms explosive mixtures with air, so its medical use was abandoned in 1925. Ethylene was thought to be safer, but it too was implicated in numerous lethal fires and explosions during anesthesia. Even so, it remained an important anesthetic into the 1960s, when it was replaced by nonflammable anesthetics such as halothane (CHBrClCF3).