Seon Oc Organic KNOWLEDGE TOOLS Thomson'NOW Throughout this chapter, sign in at veww.thomsonedu.com for online self-study and interactive tutorials based on your level of understanding, 'yge Online homework for this chapter may be assigned in Organic OWL. 31 ThomsonNNOW" Click Organic Interactive to learn how to recognize functional groups in organic molecules, ’ bye it _ Organic Compounds: Alkanes and Their Stereochemistry According to Chemical Abstracts, the publication that abstracts and indexes the chemical literature, there are more than 30 million known organic compounds. Each of these compounds has its own physical properties, such as melting point and boiling point, and each has its own chemical reactivity. Chemists have learned through many years of experience that organic com- pounds can be classified into families according to their structural features and that the members of a given family often have similar chemical behavior, Instead of 30 million compounds with random reactivity, there are a few dozen families of organic compounds whose chemistry is reasonably predictable. We'll study the chemistry of specific families throughout much of this book, begin- ning in this chapter with a look at the simplest family, the alkanes. WHY THIS CHAPTER? Alkanes are relatively unreactive, but they nevertheless provide a useful vehicle for introducing some important general ideas. In this chapter, we'll use alkanes for discussing the basic approach to naming organic compounds and for taking an initial look at some of the three-dimensional aspects of molecules, a topic of particular importance in understanding biological organic chemistry. Functional Groups ‘The structural features that make it possible to classify compounds into families are called functional groups. A functional group is a group of atoms that has a char- acteristic chemical behavior in every molecule where it occurs. For example, com- pate ethylene, a plant hormone that causes fruit to ripen, with menthene, a much more complicated molecule. Both substances contain a carbon-carbon double- bond functional group, and both therefore react with Br, in the same way to give products in which a Bratom has added to each of the doublebond carbons ( ure 3.1). This example is typical: the chemistry of every organic molecule, regardless of size and complexity, is determined by the fictional groups it contains, B —_—74 CHAPTER 3 Organic Compounds: Alkanes and Their Stereachemistry Double bond ’ CHa Figure 3.1 The reactions of [ex ethylene and menthene with bromine. In both molecules, bond funetional group has @ Ve H similar polarity pattern, so neon both molecules react with Bp HH in the same way. The sizo and ‘complexity ofthe remainders of tho molecules are nat important Hs oH Menthene [pe Bromine added a here aan ot the carbon-carbon double- Br. “Br aN a NL Bey LH nc OH 2c SH tac—cH G—CHs \ Hoc 4 Look carefully at Table 3.1 on pages 76 and 77, which lists meny of the com- mon functional groups and gives simple examples of their occurrence, Some functional groups have only carbon-carbon double or triple bonds; others have halogen atoms; and still others contain oxygen, nitrogen, or sulfur, Much of the chemistry you'll be studying is the chemistry of these functional groups. Functional Groups with Carbon—Carbon Multiple Bonds Alkenes, alkynes, and arenes (aromatic compounds) all contain carbon-carbon multiple bonds. Alkenes have a double bond, alkynes have a triple bond, and arenes have alternating double and single bonds in a six-membered ring of carbon atoms. Because of their structural similarities, these compounds also have chemical similarities. ‘ed / Alkene (aromatie ring)Alley! halide {haloalkane) Amine 3.1 Functional Groups 75 Functional Groups with Carbon Singly Bonded to an Electronegative Atom Alkyl halides (haloalkanes), alcohols, ethers, amines, thiols, sulfides, and disulfides all have a carbon atom singly bonded to an electronegative atom—halogen, oxygen, nitrogen, or sulfur. Alay! halides have a carbon atom bonded to halo- gen (-X), alcohols have a carbon atom bonded to the oxygen of a hydroxyl group (—OH), ethers have two carbon atoms bonded to the same oxygen, organophosphates have a carbon atom bonded to the oxygen of a phosphate group (-OPO,2-), amines have a carbon atom bonded to a nitrogen, thiols have a carbon atom bonded to an ~SH group, stlfides have two carbon atoms bonded to the same sulfur, and disuifides have carbon atoms bonded to two sulfurs that are joined together. In all cases, the bonds are polar, with the carbon atom bear- ing a partial positive charge (6+) and the electronegative atom bearing a partial negative charge (5—). Alcohol Ether Phosphate \ V \ \ 3. “su sey Arg So" Hs Thiol Sulfide Disulfide Functional Groups with a Carbon-Oxygen Double Bond (Carbonyl Groups) Note particularly the last seven entries in Table 3.1, which list cifferent families of compounds that contain the carbonyl group, C=O (pronounced car-bo-neel), Functional groups with a carbon-oxygen double bond are present in the great majority of organic compounds and in practically all biological molecules. ‘These compounds behave similarly in many respects but differ depending on the identity of the atoms bonded to the carbonyl-group carbon. Aldehydes have at least one hydrogen bonded to the C=O, ketones have two carbons bonded to the C=O, carboxylic acids have an ~OH group bonded to the C=O, esters have an ether-like oxygen bonded to the C=O, amides have an amine-like nitrogen