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Organic Chemistry An Introduction To understand life as we know it, we must first understand a little bit of organic chemistry. Organic molecules contain both carbon and hydrogen. Though many organic chemicals also contain other elements, it is the carbon-hydrogen bond that defines them as organic. Organic chemistry defines life. Just as there are millions of different types of living organisms on this planet, there are millions of different organic molecules, each with different chemical and physical properties. There are organic chemicals that make up your hair, your skin, your fingernails, and so on. The diversity of organic chemicals is due to the versatility of the carbon atom. Why is carbon such a special element? Let's look at its chemistry in a little more detail. Carbon (C) appears in the second row of the periodic table and has four bonding electrons in its valence shell (see our Periodic Table module for more information). Similar to other non-metals, carbon needs eight electrons to satisfy its valence shell. Carbon therefore forms four bonds with other atoms (each bond consisting of one of carbon's electrons and one of the bonding atom's electrons). Every valence electron participates in bonding, thus a carbon atom's bonds will be distributed evenly over the atom's surface. These bonds form a tetrahedron (a pyramid with a spike at the top), as illustrated below: carbon bonds - Carbon forms 4 bonds Carbon forms 4 bonds Organic chemicals get their diversity from the many different ways carbon can bond to other atoms. The simplest organic chemicals, called hydrocarbons, contain only carbon and hydrogen atoms; the simplest hydrocarbon (called methane) contains a single carbon atom bonded to four hydrogen atoms: carbon-methane - Methane - a carbon atom bonded to 4 hydrogen atoms Methane - a carbon atom bonded to 4 hydrogen atoms But carbon can bond to other carbon atoms in addition to hydrogen, as illustrated in the molecule ethane below: carbon-ethane - Ethane - a carbon-carbon bond Ethane - a carbon-carbon bond In fact, the uniqueness of carbon comes from the fact that it can bond to itself in many different ways. Carbon atoms can form long chains: carbon-hexane - Hexane - a 6-carbon chain Hexane - a 6-carbon chain branched chains: carbon-isohexane - Isohexane - a branched-carbon chain Isohexane - a branched-carbon chain rings: carbon-cyclohexane - Cyclohexane - a ringed hydrocarbon Cyclohexane - a ringed hydrocarbon There appears to be almost no limit to the number of different structures that carbon can form. To add to the complexity of organic chemistry, neighboring carbon atoms can form double and triple bonds in addition to single carbon-carbon bonds: c-ethane c-ethene c-ethyne Single bonding Double bonding Triple bonding Keep in mind that each carbon atom forms four bonds. As the number of bonds between any two carbon atoms increases, the number of hydrogen atoms in the molecule decreases (as can be seen in the figures above). Simple hydrocarbons The simplest hydrocarbons are those that contain only carbon and hydrogen. These simple hydrocarbons come in three varieties depending on the type of carbon-carbon bonds that occur in the molecule. Alkanes are the first class of simple hydrocarbons and contain only carbon-carbon single bonds. The alkanes are named by combining a prefix that describes the number of carbon atoms in the molecule with the root ending "ane". The names and prefixes for the first ten alkanes are given in the following table. Carbon Atoms Prefix Alkane Name Chemical Formula Structural Formula 1 Meth Methane CH 4 CH4 2 Eth Ethane C2H6 CH3CH3 3 Prop Propane C3H8 CH3CH2CH3 4 But Butane C4H10 CH3CH2CH2CH3 5 Pent Pentane C5H12 CH3CH2CH2CH2CH3 6 Hex Hexane C6H14 ... 7 Hept Heptane C7H16 8 Oct Octane C8H18 9 Non Nonane C9H20 10 Dec Decane C10H22 The chemical formula for any alkane is given by the expression CnH2n+2. The structural formula, shown for the first five alkanes in the table, shows each carbon atom and the elements that are attached to it. This structural formula is important when we begin to discuss more complex hydrocarbons. The simple alkanes share many properties in common. All enter into combustion reactions with oxygen to produce carbon dioxide and water vapor. In other words, many alkanes are flammable. This makes them good fuels. For example, methane is the principle component of natural gas, and butane is common lighter fluid. CH4 + 2O2 arrow CO2 + 2H2O The combustion of methane The second class of simple hydrocarbons, the alkenes, consists of molecules that contain at least one double-bonded carbon pair. Alkenes follow the same naming convention used for alkanes. A prefix (to describe the number of carbon atoms) is combined with the ending "ene" to denote an alkene. Ethene, for example is the two- carbon molecule that contains one double bond. The chemical formula for the simple alkenes follows the expression CnH2n. Because one of the carbon pairs is double bonded, simple alkenes have two fewer hydrogen atoms than alkanes. carbon-ethene - Ethene Ethene Alkynes are the third class of simple hydrocarbons and are molecules that contain at least one triple-bonded carbon pair. Like the alkanes and alkenes, alkynes are named by combining a prefix with the ending "yne" to denote the triple bond. The chemical formula for the simple alkynes follows the expression CnH2n-2. carbon-ethyne - Ethyne Ethyne Isomers Because carbon can bond in so many different ways, a single molecule can have different bonding configurations. Consider the two molecules illustrated here: C6H14 c-hexane CH3CH2CH2CH2CH2CH3 C6H14 c-isohexane CH 3 I CH3 CH2 CH CH2 CH3 Both molecules have identical chemical formulas (shown in the left column); however, their structural formulas (and thus some chemical properties) are different. These two molecules are called isomers. Isomers are molecules that have the same chemical formula but different structural formulas. Functional groups In addition to carbon and hydrogen, hydrocarbons can also contain other elements. In fact, many common groups of atoms can occur within organic molecules, these groups of atoms are called functional groups. One good example is the hydroxyl functional group. The hydroxyl group consists of a single oxygen atom bound to a single hydrogen atom (-OH). The group of hydrocarbons that contain a hydroxyl functional group is called alcohols. The alcohols are named in a similar fashion to the simple hydrocarbons, a prefix is attached to a root ending (in this case "anol") that designates the alcohol. The existence of the functional group completely changes the chemical properties of the molecule. Ethane, the two-carbon alkane, is a gas at room temperature; ethanol, the two-carbon alcohol, is a liquid. carbon-ethanol - Ethanol Ethanol Ethanol, common drinking alcohol, is the active ingredient in "alcoholic" beverages such as beer and wine. External Resources • Organic Molecular Model Kit • The Most Beautiful Molecule: The Discovery of the Buckyball • Other Recommended Products Back to top Anthony Carpi, Ph.D. "Organic Chemistry: An Introduction," Visionlearning Vol. CHE-2 (4), 2003. http://www.visionlearning.com/library/module_viewer.php?mid=60 Visionlearning Resources Glossary Library + Biology Adaptation Cells Charles Darwin I Charles Darwin II Charles Darwin III DNA I DNA II DNA III Genetics I Genetics II Taxonomy I Taxonomy II: Nomenclature + Chemistry Acids and Bases Atomic Theory I Atomic Theory II Carbohydrates Chemical Bonding Chemical Equations Chemical Reactions Fats and Proteins Matter Matter: States of Matter Nuclear Chemistry Organic Chemistry The Mole The Periodic Table of Elements Water + Earth Science Earth Structure Earth's Atmosphere Minerals I Minerals II Minerals III Plate Tectonics I Plate Tectonics II The Carbon Cycle The Hydrologic Cycle The Nitrogen Cycle The Rock Cycle + General Science Density Energy Temperature The Metric System The Scientific Method Unit Conversion + Physics Gravity Light I Light II Waves and Wave Motion + Process of Science Data: Analysis and Interpretation Data: Statistics Data: Uncertainty, Error, and Confidence Data: Using Graphs and Visual Data Ideas in Science: Scientific Controversy Ideas in Science: Theories, Hypotheses, and Laws Research Methods: Comparison Research Methods: Description Research Methods: Experimentation Research Methods: Modeling Research Methods: The Practice of Science Scientific Communication: Peer Review Scientific Communication: The How and Why of Scientific Meetings Scientific Communication: Understanding Scientific Journals and Articles Scientific Communication: Utilizing the Scientific Literature Scientific Ethics Scientific Institutions and Societies Scientists and the Scientific Community The Nature of Scientific Knowledge The Process of Science + Scientific Research Bone Changes in Rock Climbers Classic Experiment: Meselson and Stahl Creativity in Science From Stable Chromosomes to Jumping Genes Studying Climate Change with Kevin Arrigo The Case of the Ivory-billed Woodpecker + Toxicology & Pharmacology Absorption, Distribution and Storage of Chemicals + Trigonometry Wave Mathematics + Interactive Animations Bohr's Atom: Quantum Behavior in Hydrogen The reaction of sodium with chlorine An example of an interactive learning tool: Mid-Ocean Ridges Leaning Tower of Pisa Experiment The formation of water The Virtual Animal Cell Nuclear Fusion Two Types of Nuclear Chain Reactions Dalton's Playhouse Darwin's Finches The Illustrated Animal Cell States of Matter The Illustrated Periodic Table External Resources • Organic Molecular Model Kit • The Most Beautiful Molecule: The Discovery of the Buckyball • Other Recommended Products Quotes ...one or two atoms can convert a fuel to a poison, change a color, render an inedible substance edible, or replace a pungent odor with a fragrant one. 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