第一学期期末（卢家锡）.ppt

有机化学习题课 Alcohols Playing as Acids Conversion to Mesylates and Tosylates Conversion to Alkyl Halides Oxidation Reactions of Alcohols Alcohols as Acids Conversion of Alcohols into Mesylates and Tosylates Mesylates and Tosylates in SN2 Reactions Conversion of Alcohols to Alkyl Halides Reaction of Alcohols with PBr3 or SOCl2 Oxidation of Secondary Alcohols Secondary alcohols can be oxidized to ketones. Oxidation of Primary Alcohols Oxidation of Alcohols to Aldehyde Ethers and Epoxides Ether Cleavage by Strong Acid Ring Opening of an Epoxide Acid-Catalyzed Base-Catalyzed Ether Cleavage by Strong Acid Ring Opening of an Epoxide Acid-Catalyzed Base-Catalyzed Aromatic Compounds Hückel’s rule Electrophilic Aromatic Substitution Halogenation Nitration Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation (Clemmensen Reduction) Effect of Substituents on Reactivity and Orientation Other Reactions Oxidation Reduction (Birch Reduction) Benzylic halogenation Hückel’s rule Monocyclic conjugated polyenes Planar (4n + 2) ? electrons The Annulenes Aromatic Ions Benzenoid Aromatic Compounds Nonbenzenoid Aromatic Compounds Heterocyclic Aromatic Compounds Electrophilic Aromatic Substitution Limitations of Friedel-Crafts Alkylation Other carbocationlike species Friedel-Crafts Acylation Synthetic Applications Cloromethylation and Gatterman-Koch Reaction Effect of Substituents on Reactivity and Orientation Ortho-para directors Oxidation of the Benzene Ring Oxidation of the Side Chain Reductions of Aromatic Compounds Benzylic halogenation Conjugated Unsaturated Systems Allylic halogenation 1,4-Addition Diels-Alder Reaction Allylic Chlorination (High Temperature) Allylic Bromination with NBS (Low Concentration of Br2) Kinetic Control versus Thermodynamic Control Stereochemistry of the Diles-Alder Reaction Syn Addition Molecular Orbital Considerations That favor an Endo Transition State Phenols Reaction of Phenols Playing as Acids Conversion to Ethers by Williamson Synthes