columbia大学有机化学课件 （四十）.pptVIP

Chapter 9Alkynes 9.1Sources of Alkynes Acetylene Industrial preparation of acetylene isby dehydrogenation of ethylene 9.2Nomenclature Nomenclature 9.3Physical Properties of Alkynes 9.4Structure and Bonding in Alkynes:sp Hybridization Structure linear geometry for acetylene Cycloalkynes Cyclononyne is the smallest cycloalkyne stable enough to be stored at room temperaturefor a reasonable length of time. Cyclooctyne polymerizeson standing. sp Hybridization in Acetylene sp Hybridization in Acetylene s Bonds in Acetylene p Bonds in Acetylene p Bonds in Acetylene Figure 9.3 Electrostatic Potential in Acetylene Table 9.1Comparison of Ethane, Ethylene, and Acetylene CH3CH3 800°C 1150°C cost of energy makes acetylene a more expensive industrial chemical than ethylene H2C CH2 H2C CH2 HC CH H2 + H2 + HC CH Acetylene and ethyne are both acceptableIUPAC names for Higher alkynes are named in much the sameway as alkenes except using an -yne suffixinstead of -ene. HC CCH3 Propyne HC CCH2CH3 1-Butyne (CH3)3CC CCH3 4,4-Dimethyl-2-pentyne The physical properties of alkynes are similar to those of alkanes and alkenes. C C H H 120 pm 106 pm 106 pm C C CH3 H 121 pm 146 pm 106 pm 2s 2p 2sp Mix together (hybridize) the 2s orbital and one of the three 2p orbitals 2p 2sp Mix together (hybridize) the 2s orbital and one of the three 2p orbitals 2p Each carbon has two half-filled sp orbitalsavailable to form s bonds. Each carbon isconnected to ahydrogen by as bond. The twocarbons are connectedto each other by as bond and two p bonds. Figure 9.2 (a) One of the twop bonds in acetylene isshown here.The second pbond is at rightangles to the first. Figure 9.2 (b) This is the secondof the twop bonds in acetylene. Figure 9.2 (c) The region of highest negative charge lies aboveand below the molecular plane in ethylene. The region of highest negative charge encirclesthe molecule around itscenter in acetylene. C—C distance C—H distance H—C—C angles C—C BD