20.1 Hydrocarbons

The largest database This is the Beilstein database, now available through the Reaxys site (www.elsevier.com/online-tools/reaxys). of organic compounds lists about 10 million substances, which include compounds originating from living organisms and those synthesized by chemists. The number of potential organic compounds has been estimated Peplow, Mark. “Organic Synthesis: The Robo-Chemist,” Nature 512 (2014): 20–2. at 10 ⁶⁰ —an astronomically high number. The existence of so many organic molecules is a consequence of the ability of carbon atoms to form up to four strong bonds to other carbon atoms, resulting in chains and rings of many different sizes, shapes, and complexities.

The simplest organic compounds contain only the elements carbon and hydrogen, and are called hydrocarbons. Even though they are composed of only two types of atoms, there is a wide variety of hydrocarbons because they may consist of varying lengths of chains, branched chains, and rings of carbon atoms, or combinations of these structures. In addition, hydrocarbons may differ in the types of carbon-carbon bonds present in their molecules. Many hydrocarbons are found in plants, animals, and their fossils; other hydrocarbons have been prepared in the laboratory. We use hydrocarbons every day, mainly as fuels, such as natural gas, acetylene, propane, butane, and the principal components of gasoline, diesel fuel, and heating oil. The familiar plastics polyethylene, polypropylene, and polystyrene are also hydrocarbons. We can distinguish several types of hydrocarbons by differences in the bonding between carbon atoms. This leads to differences in geometries and in the hybridization of the carbon orbitals.

Alkanes

Alkanes , or saturated hydrocarbons , contain only single covalent bonds between carbon atoms. Each of the carbon atoms in an alkane has sp ³ hybrid orbitals and is bonded to four other atoms, each of which is either carbon or hydrogen. The Lewis structures and models of methane, ethane, and pentane are illustrated in [link] . Carbon chains are usually drawn as straight lines in Lewis structures, but one has to remember that Lewis structures are not intended to indicate the geometry of molecules. Notice that the carbon atoms in the structural models (the ball-and-stick and space-filling models) of the pentane molecule do not lie in a straight line. Because of the sp ³ hybridization, the bond angles in carbon chains are close to 109.5°, giving such chains in an alkane a zigzag shape.

The structures of alkanes and other organic molecules may also be represented in a less detailed manner by condensed structural formulas (or simply, condensed formulas ). Instead of the usual format for chemical formulas in which each element symbol appears just once, a condensed formula is written to suggest the bonding in the molecule. These formulas have the appearance of a Lewis structure from which most or all of the bond symbols have been removed. Condensed structural formulas for ethane and pentane are shown at the bottom of [link] , and several additional examples are provided in the exercises at the end of this chapter.