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World of Chemistry Chapter 20—Organic Chemistry Price Definition: Organic chemistry is the study of carbon-containing compounds and their properties. Overview: Polymers (long chain-like molecules) and other organic compounds have changed the world. Nylon, Velcro, Kevlar and other polymers are used every day. This is made possible by 2 group 4 elements: Carbon and silicon. I. Section 20.1—Carbon bonding A. There are several million known carbon-chain (organic) molecules which are the basis for respiration and reproduction in all plants and animals. B. Carbon forms strong bonds to itself and to many other elements C. More than any other element, carbon can form long chains of molecules II. Section 20.2—Alkanes A. Alkanes are saturated hydrocarbons—which means that they are a chain of carbon and hydrogen atoms where each carbon atom is bound to 4 other atoms with no double or triple bonds B. The simplest alkane is methane—CH4 C. All alkanes can be represented by the general formula: CnH2n+2 III. Section 20.3—Isomerism and Structural Formulas A. An isomer is a molecule with the same formula but different arrangement as its parent molecule B. Different isomers have different properties due to their different arrangements IV. Section 20.4—Naming Alkanes A. Rules for naming alkanes Rules for Naming Alkanes 1. Find the longest continuous chain of carbon atoms. This chain (called the parent chain) determines the base alkane name. 2. Number the carbons in the parent chain, starting at the end closest to any branching (the first alkyl substituent). When a substituent occurs the same number of carbons from each end, use the next substituent (if any) to determine from which end to start numbering. 3. Using the appropriate name for each alkyl group, specify its position on the parent chain with a number. 4. When a given type of alkyl group occurs more than once, attach the appropriate prefix to the alkyl name. 5. The alkyl groups are listed in alphabetical order, disregarding any prefix V. VI. Section 20.5—Petroleum A. Petroleum is a thick, dark liquid composed largely of hydrocarbons containing from 5 to over 25 carbon atoms (also known as “crude oil”.) B. Natural gas (which is found with petroleum deposits) contains mostly methane as well as significant amounts of ethane, propane and butane. C. Petroleum probably formed from the remains of marine organisms that lived about 500 million years ago. D. When petroleum and natural gas are burned they release energy that originally came from the sun…photosynthesis stored energy in the plants and by burning their decay products we can release that energy. These are fossil fuels Section 20.6—Reactions of Alkanes A. At high temperatures alkanes react vigorously with oxygen…these are combustion reactions B. Substitution reactions occur when one or more hydrogen atoms are replaced by different atoms Example: CH4 + Cl2 CH3Cl+ HCl C. Dehydrogenation reactions occur when a hydrogen atom is removed and a double bond is formed VII. Section 20.7—Alkenes and Alkynes A. Alkanes are saturated hydrocarbons (each carbon atom is bonded to 4 other atoms by single bonds) B. Alkenes are unsaturated hydrocarbons where a hydrogen atom is removed and a double bond forms C. Alkynes are unsaturated hydrocarbons where a hydrogen atom is removed and a triple bond forms Rules for Naming Alkenes and Alkynes 1. Select the longest continuous chain of carbon atoms that contains the double or triple bond. 2. For an alkene, the root name of the carbon chain is the same as the alkane except that the –ane ending is replaced by –ene. For an alkyne, the –ane is replaced by –yne. 3. Number the parent chain, starting at the end closest to the double or triple bond. The location of the multiple bond is given by the lowest-numbered carbon involved in the bond. 4. Substituents on the parent chain are treated the same way as in naming alkanes. D. Reactions of alkenes 1. addition reactions=new atoms form single bonds to the carbons formerly involved in multiple bonds 2. hydrogenation reactions=replaces multiple bonds with hydrogen atoms 3. halogenation reactions=replaces multiple bonds with halogen atoms 4. polymerization reactions=many small molecules are joined together to form a large molecule. VIII.Section 20.8—Aromatic Hydrocarbons A. Wintergreen, cinnamon and vanilla are all aromatic hydrocarbons. B. Aromatic hydrocarbons all have a six-carbon atom structure called a “benzene ring”. IX. X. Section 20.9--Naming Aromatic Compounds A. Monosubstituted Benzenes (formed when one of the hydrogen atoms on the ring is replaced) are named by adding the substituent name as a prefix to “benzene”. B. Disubstituted Benzenes (formed when more than one hydrogen atom on the ring is replaced) are named by 2 different methods described on pp.656-7 Section 20.10—Functional Groups A. Definition: A Functional Group is an atom or group of atoms that are added to a hydrocarbon chain. B. Functional groups include: 1. Halohydrocarbons 2. Alcohols 3. Ethers XI. 4. Aldehydes 5. Ketones 6. Carboxylic Acids 7. Esters 8. Amines C. Rules for naming the functional groups are found on pp.660-670 (Sec. 20.11-20.15) Polymers A. Polymers are large, chain-like molecules that are built from smaller molecules called monomers. B. Plastics (like polyethylene) are polymers and can be very versatile. C. Teflon, vinyl, Dacron (a polyester), styrene and nylon are all common polymers.