Chapter 2 Notes - 9/8/2010 Carbon-carbon Covalent Bonds...

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9/8/2010 1 Chapter 2 Representative Carbon Compounds: Functional Groups, Intermolecular Forces and Infrared (IR) Spectroscopy Chapter 2 2 l Carbon-carbon Covalent Bonds c Carbon forms strong covalent bonds to other carbons and to other elements such as hydrogen, oxygen, nitrogen and sulfur b This accounts for the vast variety of organic compounds possible c Organic compounds are grouped into functional group families b A functional group is a specific grouping of atoms ( e.g . carbon- carbon double bonds are in the family of alkenes) b An instrumental technique called infrared (IR) spectroscopy is used to determine the presence of specific functional groups Chapter 2 3 l Hydrocarbons: Representative Alkanes, Alkenes Alkynes, and Aromatic Compounds b Hydrocarbons contain only carbon and hydrogen atoms b Subgroups of Hydrocarbons: h Alkanes contain only carbon-carbon single bonds h Alkenes contain one or more carbon-carbon double bonds h Alkynes contain one or more carbon-carbon triple bonds h Aromatic hydrocarbons contain benzene-like stable structures (discussed later) b Saturated hydrocarbons: contain only carbon-carbon single bonds e.g. alkanes b Unsaturated hydrocarbons: contain double or triple carbon- carbon bonds e.g. alkene, alkynes, aromatics h Contain fewer than maximum number of hydrogens per carbon h Capable of reacting with H 2 to become saturated Chapter 2 4 l Representative Hydrocarbons c Alkanes b Principle sources of alkanes are natural gas and petroleum h Smaller alkanes (C 1 to C 4 ) are gases at room temperature b Methane is h A component of the atmosphere of many planets h Major component of natural gas h Produced by primitive organisms called methanogens found in mud, sewage and cows’ stomachs
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9/8/2010 2 Chapter 2 5 c Alkenes b Ethene (ethylene) is a major industrial feedstock h Used in the production of ethanol, ethylene oxide and the polymer polyethylene b Propene (propylene) is also very important in industry h Molecular formula C 3 H 6 h Used to make the polymer polypropylene and is the starting material for acetone b Many alkenes occur naturally Chapter 2 6 c Alkynes b Ethyne (acetylene) is used in welding torches because it burns at high temperature b Many alkynes are of biological interest h Capillin is an antifungal agent found naturally h Dactylyne is a marine natural product h Ethinyl estradiol is a synthetic estrogen used in oral contraceptives Chapter 2 7 c Benzene: A Representative Hydrocarbon b Benzene is the prototypical aromatic compound h The Kekulé structure (named after August Kekulé who formulated it) is a six- membered ring with alternating double and single bonds b Benzene does not actually have discreet single and double carbon-carbon bonds h All carbon-carbon bonds are exactly equal in length (1.38 Å) h This is between the length of a carbon-carbon single bond and a carbon-carbon double bond b Resonance theory explains this by suggesting there are two resonance hybrids that contribute equally to the real structure
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This note was uploaded on 05/16/2011 for the course CHEM BIO 20a3 taught by Professor Stover during the Fall '10 term at McMaster University.

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Chapter 2 Notes - 9/8/2010 Carbon-carbon Covalent Bonds...

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