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Hydrocarbon- Alkanes, Alkenes, Alkynes
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Organic Nomenclature. What are aliphatic compounds or aliphatic hydrocarbons? An aliphatic compound or aliphatic hydrocarbon is an organic compound containing hydrogen and carbon atoms that are usually linked together in chains that are straight. The term Aliphatic has been derived from the Greek word âAleipharâ which translates to âfatâ. It is used to describe hydrocarbons that are obtained by the chemical degradation of oils or fats. What are aliphatic compounds or aliphatic hydrocarbons? The simplest organic compounds are those composed of only two elements: carbon and hydrogen. These compounds are called hydrocarbons. Hydrocarbons are separated into two types: aliphatic hydrocarbons and aromatic hydrocarbons. Aliphatic hydrocarbons are hydrocarbons based on chains of C atoms. There are three types of aliphatic hydrocarbons: Alkanes are aliphatic hydrocarbons with only single covalent bonds. Alkenes are hydrocarbons that contain at least one CâC double bond, and alkynes are hydrocarbons that contain a CâC triple bond. Occasionally, we find an aliphatic hydrocarbon with a ring of C atoms; these hydrocarbons are called cycloalkanes (or cycloalkenes or cycloalkynes). The simplest alkanes have their C atoms bonded in a straight chain; these are called normal alkanes. They are named according to the number of C atoms in the chain. The smallest alkane is methane: molecule is three dimensional, with the H atoms in the positions of the four corners of a tetrahedron. The diagrams representing alkanes are called structural formulas because they show the structure of the molecule. As molecules get larger, structural formulas become more and more complex. One way around this is to use a condensed structural formula, which lists the formula of each C atom in the backbone of the Molecule. The condensed formulas show hydrogen atoms right next to the carbon atoms to which they are attached, as illustrated for butane: The ultimate condensed formula is a line-angle formula (or line drawing) , in which carbon atoms are implied at the corners and ends of lines, and each carbon atom is understood to be attached to enough hydrogen atoms to give each carbon atom four bonds. For example, we can represent pentane (CH3CH2CH2CH2CH3) and isopentane [(CH3)2CHCH2CH3] as follows: Unsaturated Hydocarbons: Alkenes and Alkynes Alkenes Organic compounds that contain one or more double or triple bonds between carbon atoms are described as unsaturated. Unsaturated hydrocarbons have less than the maximum number of H atoms possible. Unsaturated hydrocarbon molecules that contain one or more double bonds are called alkenes. Carbon atoms linked by a double bond are bound together by two bonds, one Ď bond and one Ď bond. Double and triple bonds give rise to a different geometry around the carbon atom that participates in them, leading to important differences in molecular shape and properties. The differing geometries are responsible for the different properties of unsaturated versus saturated fats. Naming Alkenes and Alkynes Alkenes and alkynes are named in a similar fashion. The biggest difference is that when identifying the longest carbon chain, it must contain the CâC double or triple bond. Furthermore, when numbering the main chain, the double or triple bond gets the lowest possible number. This means that there may be longer or higher-numbered substituents than may be allowed if the molecule were an alkane. For example, this molecule is 2,4-dimethyl-3-heptene (note the number and the hyphens that indicate the position of the double bond). â Unsaturated Hydocarbons: Alkenes and Alkynes Unsaturated Hydocarbons: Alkenes and Alkynes Alkynes Hydrocarbon molecules with one or more triple bonds are called alkynes; they make up another series of unsaturated hydrocarbons. Two carbon atoms joined by a triple bond are bound together by one Ď bond and two Ď bonds. The sp-hybridized carbons involved in the triple bond have bond angles of 180°, giving these types of bonds a linear, rod-like shape. The simplest member of the alkyne series is ethyne, C2H2, commonly called acetylene. The Lewis structure for ethyne, a linear molecule, is: Properties of Unsaturated Hydocarbons: Alkenes and Alkynes Ethylene (the common industrial name for ethene) is a basic raw material in the production of polyethylene and other important compounds. Over 135 million tons of ethylene were produced worldwide in 2010 for use in the polymer, petrochemical, and plastic industries. Ethylene is produced industrially in a process called cracking, in which the long hydrocarbon chains in a petroleum mixture are broken into smaller molecules. Halogens can also react with alkenes and alkynes, but the reaction is different. In these cases, the halogen reacts with the CâC double or triple bond and inserts itself onto each C atom involved in the multiple bonds. This reaction is called an addition reaction. One example is Properties of Unsaturated Hydocarbons: Alkenes and Alkynes Hydrogen can also be added across a multiple bond; this reaction is called a hydrogenation reaction. In this case, however, the reaction conditions may not be mild; high pressures of H2 gas may be necessary. A platinum or palladium catalyst is usually employed to get the reaction to proceed at a reasonable pace: CH2=CH2+H2âmetalcatalystCH3CH3 CH2=CH2+H2âmetalcatalystCH3CH3. HYDROCARBONHydrocarbon bondsHYDROCARBON 1Aromatic hydrocarbonCreate a quiz about hydrocarbon Organic Nomenclature. Hydrocarbon Derivatives: ALCOHOL School Logo An alcohol is an organic compound with a hydroxyl (OH) functional group on an aliphatic carbon atom. Because OH is the functional group of all alcohols, we often represent alcohols by the general formula ROH, where R is an alkyl group. Hydrocarbon Derivatives: ETHER School Logo Ethers are a class of compounds that contain an ether group- an oxygen atom bonded to two organyl groups (alkyl or aryl). They have the general formula R-O-Râ . Hydrocarbon Derivatives: ALDEHYDE School Logo Aldehydes are also known as formyl or methanoyl group. It derived their name from the dehydration of alcohols and contain the carbonyl group bonded to at least one hydrogen atom. Hydrocarbon Derivatives: KETONE School Logo Ketone is any of a class of organic compounds characterized by the presence of a carbonyl group in which the carbon atom is covalently bonded to an oxygen atom. Hydrocarbon Derivatives: CARBOXYLIC ACID School Logo A carboxylic acid is an organic compound that contains the carboxyl functional group. The general formula for a carboxylic acid is R-COOH. The carbon atom of the carboxyl group may be attached to a hydrogen atom or to a carbon chain. Hydrocarbon Derivatives: Ester School Logo Esters are organic compounds that are derived from carboxylic acids. The carboxyl group âCOOH is contained in a carboxylic acid. The hydrogen in this group is being replaced by a hydrocarbon group in esters. These hydrocarbon groups could be a methyl, ethyl, or phenyl group. Hydrocarbon Derivatives: Amine School Logo An amine is a derivative of ammonia in which one, two, or all three hydrogen atoms are replaced by hydrocarbon groups. The amine functional group is as follows: primary, secondary, or tertiary by the number of hydrocarbon groups attached to the nitrogen atom.Hydrocarbon Derivatives: Amine School Logo An amine is a derivative of ammonia in which one, two, or all three hydrogen atoms are replaced by hydrocarbon groups. The amine functional group is as follows: primary, secondary, or tertiary by the number of hydrocarbon groups attached to the nitrogen atom. Lipids are large, nonpolar organic molecules. They do not dissolve in water. Lipids include triglycerides (trie-GLIS-uhr-IEDZ), phospho- lipids, steroids, waxes, and pigments. Lipid molecules have a higher ratio of carbon and hydrogen atoms to oxygen atoms than carbohydrates have. Because lipid molecules have larger numbers of carbon-hydrogen bonds per gram than other organic com- pounds do, they store more energy per gram. Fatty Acids Fatty acids are unbranched carbon chains that make up most lipids. Figure 3-10 shows that a fatty acid contains a long carbon chain (from 12 to 28 carbons) with a carboxyl group, âCOOH, attached at one end. The two ends of the fatty-acid molecule have different properties. The carboxyl end is polar and is thus hydrophilic or attracted to water molecules. In contrast, the hydro- carbon end of the fatty-acid molecule is nonpolar. This end tends not to interact with water molecules and is said to be hydrophobic (HIE-droh-FOH-bik), or âwater fearing.â In saturated fatty acids, such as palmitic acid, which is shown in Figure 3-10, each carbon atom is covalently bonded to four atoms. The carbon atoms are in effect full, or saturated. In contrast, linoleic acid, also shown in Figure 3-10, has carbon atoms that are not bonded to the maximum number of atoms to which they can bond. Instead, they have formed double bonds within the carbon chain. This type of fatty acid is said to be unsaturated. Triglycerides Three classes of lipids important to living things contain fatty acids: triglycerides (fats), phospholipids, and waxes. A triglyceride is composed of three molecules of fatty acid joined to one molecule of the alcohol glycerol. Saturated triglycerides are composed of saturated fatty acids. They typically have high melting points and tend to be hard at room temperature. Common dietary saturated triglycerides include butter and fats in red meat. In contrast, unsaturated triglycerides are composed of unsaturated fatty acids and are usually soft or liquid at room temperature. Unsaturated triglycerides are found primarily in plant seeds where they serve as an energy and carbon source for germinating plants. Phospholipids Phospholipids have two, rather than three, fatty acids attached to a molecule of glycerol. They have a phosphate group attached to the third carbon of the glycerol. As shown in Figure 3-11, the cell membrane is made of two layers of phospholipids, called the lipid bilayer. The inability of lipids to dissolve in water allows the mem- brane to form a barrier between the inside and outside of the cell. Hydrophilic âheadâ Phospholipids Hydrophobic âtailâ Phospholipids Water Water The lipid bilayer of a cell membrane is a double row of phospholipids.The âtailsâ face each other.The âheadâ of a phospholipid, which contains a phosphate group, is polar and hydrophilic.The two tails are two fatty acids and are nonpolar and hydrophobic. FIGURE 3-11 H C H C O OH H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H C H H H H C H H C H H C H H C H H C H C O OH H C H H C H H C H C H C H C H H C H H C H C H H C H H C H C H H H H C H Fatty acids have a polar carboxyl head, highlighted in purple, and a nonpolar hydrocarbon tail, highlighted in green. FIGURE 3-10 Palmitic acid Linoleic acid mb06se_bchs02.qxd 5/18/07 10:49 AM Page 59 60 CHAPTER 3 1. Compare the structure of monosaccharides, dis- accharides, and polysaccharides. 2. How are proteins constructed from amino acids? 3. How do amino acids differ from one another? 4. Describe a model of enzyme action. 5. Why do phospholipids orient in a bilayer when in a watery environment, such as a cell? 6. Describe how the three major types of lipids differ in structure from one another. 7. What are the functions of the two types of nucleic acids? CRITICAL THINKING 8. Applying Information Before a long race, run- ners often âcarbo load.â This means that they eat substantial quantities of carbohydrates. How might this help their performance? 9. Recognizing Relationships High temperatures can weaken bonds within a protein molecule. How might this explain the effects of using a hot curling iron or rollers in oneâs hair? 10. Applying Information You want to eat more unsaturated than saturated fats. Name examples of foods you would eat more of and less of. SECTION 2 REVIEW Waxes A wax is a type of structural lipid consisting of a long fatty-acid chain joined to a long alcohol chain. Waxes are waterproof, and in plants, form a protective coating on the outer surfaces. Waxes also form protective layers in animals. For example, earwax helps pre- vent microorganisms from entering the ear canal. Steroids Unlike most other lipids, which are composed of fatty acids, steroid molecules are composed of four fused carbon rings with various functional groups attached to them. Many animal hor- mones, such as the male hormone testosterone, are steroid com- pounds. One of the most familiar steroids in humans is cholesterol. Cholesterol is needed by the body for nerve and other cells to func- tion normally. It is also a component of the cell membrane. NUCLEIC ACIDS Nucleic acids are very large and complex organic molecules that store and transfer important information in the cell. There are two major types of nucleic acids: deoxyribonucleic acid and ribonucleic acid. Deoxyribonucleic acid, or DNA, contains information that deter- mines the characteristics of an organism and directs its cell activi- ties. Ribonucleic (RIE-boh-noo-KLEE-ik) acid, or RNA, stores and transfers information from DNA that is essential for the manufactur- ing of proteins. Some RNA molecules can also act as enzymes. Both DNA and RNA are polymers, composed of thousands of linked monomers called nucleotides (NOO-klee-uh-TIEDS). As shown in Figure 3- 12, each nucleotide is made of three main components: a phosphate group, a five-carbon sugar, and a ring-shaped nitrogenous base.