Chapter 9 Alkynes 有机化学英文版教学课件（美国达拉斯社区学院） 《Organic Chemistry 5th Edition (L.G. Wade JR.)》.pptVIP

Chapter 9 Chapter 9Alkynes Introduction Alkynes contain a triple bond. General formula is CnH2n-2 Two elements of unsaturation for each triple bond. Some reactions are like alkenes: addition and oxidation. Some reactions are specific to alkynes.  = Nomenclature: IUPAC Find the longest chain containing the triple bond. Change -ane ending to -yne. Number the chain, starting at the end closest to the triple bond. Give branches or other substituents a number to locate their position. = Name these: Additional Functional Groups All other functional groups, except ethers and halides have a higher priority than alkynes. For a complete list of naming priorities, look inside the back cover of your text.  = Examples Common Names Named as substituted acetylene. Physical Properties Nonpolar, insoluble in water. Soluble in most organic solvents. Boiling points similar to alkane of same size. Less dense than water. Up to 4 carbons, gas at room temperature.  = Acetylene Acetylene is used in welding torches. In pure oxygen, temperature of flame reaches 2800?C. It would violently decompose to its elements, but the cylinder on the torch contains crushed firebrick wet with acetone to moderate it.  = Synthesis of Acetylene Heat coke with lime in an electric furnace to form calcium carbide. Then drip water on the calcium carbide. Electronic Structure The sigma bond is sp-sp overlap. Bond Lengths More s character, so shorter length. Three bonding overlaps, so shorter. Acidity of Alkynes Terminal alkynes, R-C?C-H, are more acidic than other hydrocarbons. Acetylene ? acetylide by NH2-, but not by OH- or RO-. More s character, so pair of electrons in anion is held more closely to the nucleus. Less cha