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TOPIC 3. ALKANES (chapter 4 and parts of chapters 7 and 10) Lect Topics Reading L6 SYSTEMATIC IUPAC NOMENCLATURE OF ALKANES Linear (Unbranched) Alkanes Branched alkanes 4.1 Introduction to Alkanes and Cycloalkanes 4.2 Shapes of Alkanes NAMING OTHER COMPOUNDS Alcohols Alkyl Halides Cyclic Alkanes Bicyclic Compounds Alkenes Cyclic Alkenes Bicyclic alkanes 4.3 IUPAC Nomenclature of Alkanes, Alkyl Halides, and Alcohols 4.4 Nomenclature of Cycloalkanes 4.5 Nomenclature of Alkenes and Cycloalkenes 4.6 Nomenclature of Alkynes 4.15 Bicyclic and Polycyclic Alkanes MOLECULAR FORMULA Differentiating Alkenes and Cycloalkanes PHYSICAL PROPERTIES OF ALKANES 4.18 Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency th (8 ed.: section 7.15) 4.7 Physical Properties of Alkanes and Cycloalkanes CONFORMATIONAL ANALYSIS: ROTATION AROUND C-C SINGLE BONDS Ethane Butane 4.8 Sigma Bonds and Bond Rotation 4.9 Conformational Analysis of Butane RELATIVE STABILITY OF CYCLOALKANES 4.10 The Relative Stabilities of Cycloalkanes: Ring Strain CONFORMATIONAL ANALYSIS OF SUBSTITUTED CYCLOHEXANES The Shape of Cyclohexane cis and trans Stereoisomers Ring Inversion (“Ring Flip”) Conformational Preferences of Substituted Cyclohexanes Conformational Preferences of Disubstituted Cyclohexanes Conformational Preferences of Disubstituted Cyclohexanes Bearing Different Substituents 4.11 The Origin of Ring Strain in Cyclopropane and Cyclobutane: Angle Strain and Torsional Strain 4.12 Conformations of Cyclohexane 4.13 Substituted Cyclohexanes: Axial and Equatorial Hydrogen Atoms 4.14 Disubstituted Cycloalkanes: Cis – Trans Isomerism FREE-RADICAL HALOGENATION OF ALKANES Overall Reaction Mechanism Regioselectivity Origin of Regioselectivity Energetics 4.16 10.2 10.3 10.4 10.5 10.6 SYNTHESES OF ALKANES Hydrogenation of Alkenes and Alkynes 4.17 Synthesis of Alkanes and Cycloalkanes L7 L8 L9 NOT COVERED UNTIL TOPIC 9: 4.19 13 C NMR Spectroscopy – A Practical Introduction Chemical Reactions of Alkanes Homolytic Bond Dissociation Energies The Reactions of Alkanes with Halogens Chlorination of Methane: Mechanism of Reaction Chlorination of Methane: Energy Changes Halogenation of Higher Alkanes
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