Chapter 7 STRUCTURE AND SYNTHESIS OF ALKENES Reference: Organic Chemistry", L.G. Wade, Printice Hall, 8th Edition 1 7.1 Introduction Alkenes are hydrocarbons with carbon–carbon double bonds. Alkenes are sometimes called olefins 7.2 The Orbital Description of the Alkene Double Bond 7.21 The Sigma Bond Framework Reference: Organic Chemistry", L.G. Wade, Printice Hall, 8th Edition 2 7.22 The Pi Bond 7.23 Elements of Unsaturation Alkenes are said to be unsaturated because they are capable of adding hydrogen in the presence of a catalyst. 3 7.3 Nomenclature of Alkenes Reference: Organic Chemistry", L.G. Wade, Printice Hall, 8th Edition 4 7.4 Nomenclature of Cis-Trans Isomers 7.41 Cis-Trans Nomenclature 7.42 E-Z Nomenclature To name an alkene by the E-Z system, mentally separate the double bond into its two ends. Remember how you used the Cahn–Ingold–Prelog rules 5 Reference: Organic Chemistry", L.G. Wade, Printice Hall, 8th Edition 6 7.5 Physical Properties of Alkenes 7 Reference: Organic Chemistry", L.G. Wade, Printice Hall, 8th Edition 7.6 Alkene Synthesis by Elimination of Alkyl Halides Dehydrohalogenation is the elimination of a hydrogen and a halogen from an alkyl halide to form an alkene • Dehydrohalogenation by the E2 Mechanism Example Reference: Organic Chemistry", L.G. Wade, Printice Hall, 8th Edition 8 7.7 Alkene Synthesis by Dehydration of Alcohols Dehydration of alcohols is a common method for making alkenes. The word dehydration literally means “removal of water.” The Mechanism Reference: Organic Chemistry", L.G. Wade, Printice Hall, 8th Edition 9 7.8 Alkene Synthesis by High-Temperature Industrial Methods 7.81 Catalytic Cracking of Alkanes The least expensive way to make alkenes on a large scale is by the catalytic cracking of petroleum 7.82 Dehydrogenation of Alkanes Dehydrogenation is the removal of H2 from a molecule, just the reverse of hydrogenation. Dehydrogenation of an alkane gives an alkene Reference: Organic Chemistry", L.G. Wade, Printice Hall, 8th Edition 10