生物化学 Chapter 9 Alkynes.ppt

Chapter 9 Exercises 9.1---9.8 9.12----9.33 §9.1 Sources of Alkynes Acetylene Industrial preparation of acetylene isby dehydrogenation of ethylene Naturally Occurring Alkynes §9.2 Nomenclature In naming alkynes the IUPAC rules for hydrocarbons are followed and suffix –ane is replaced by –yne. The position of the triple bond along the chain is specified by the lowest possible number. The —C≡CH group is named as a substituent, it is designated as an ethynyl group. If both double and triple bonds are present in the parent chain, the ending becomes –enyne. Numbering is such as to give the lowest possible number to the double and triple bonds, irrespective of whether –ene or –yne has the lower number. When either group can be assigned the same number, -ene has the lower- number priority. -enyne -dienyne -trienyne -enediyne -diene -diyne 3-penten-1-yne 3-戊烯-1-炔 ( 书写时先烯后炔 ) §9.3 Physical Properties of Alkynes The physical properties of alkynes are similar to those of alkanes and alkenes. As with hydrocarbons in general, alkynes are non-polar and are insoluble in water but soluble in non-polar organic solvents §9.4 Structure and Bonding in Alkynes:sp Hybridization linear geometry for acetylene Structural Feature of Ethane, Ethene and Acetylene The carbon atoms of acetylene are connected by a ? + ? + ? triple bond. H3CH H2NH CH3C≡CH CH3CH2OH HOH Pka 49 34 25 15.9 15.74 The two separate perpendicular (垂直的) p molecular orbitals ? Bonds in Acetylene ? Bonds in Acetylene Electrostatic Potential in Acetylene The p bonds are a region of high electron density (red) so alkynes are typically nucleophiles. Alkynes typically undergo addition reactions in which one or both of the p-bonds are converted to new s bonds. Terminal alkynes, R-C≡C-H, are quite acidic (indicated by blue) for hydrocarbons, pKa = 26 Deprotonation of a terminal acetylene g