浙江大学 英文 有机化学.ppt

Organic Chemistry 俞永平 浙江大学药学院,1710 yongpingyu@; Tel: Organic Reactions, Synthesis The first organic synthesis was accomplished by Friedrich Wohler in 1828 Alkanes and Cycloalkanes Alkanes: Cycloalkanes Alkanes are characterized by a general inertness to many chemical reagents When heated, alkanes can react with chlorine, bromine. Synthesis of alkanes and cycloalkanes A: Hyrogenation of alkenes and alkynes General Reaction: Synthesis of alkanes and cycloalkanes Specific examples Synthesis of alkanes and cycloalkanes Synthesis of alkanes and cycloalkanes B: Reduction of Alkyl Halides General Reaction: Zinc atoms transfer electrons to carbon atom of alkyl halide: Synthesis of alkanes and cycloalkanes Specific Examples Synthesis of alkanes and cycloalkanes Alyklation of terminal alkynes General reaction Specific reaction Synthesis of alkanes and cycloalkanes Specific reaction Alkyl Halides: Nucleophilic Substitution and Elimination Reactions When does the carbon-halogen bond break? A Mechanism for the SN2 Reaction Reaction: Mechanism: The stereochemistry of SN2 Reaction The nucleophile attacks from the back side, that is, from the side directly opposite the leaving group. This mode of attack causes a change in the configuration. The stereochemistry of SN2 Reaction A Mechanism for the SN1 Reaction Reactions: Step 1: A Mechanism for the SN1 Reaction Step 2: Step 3: The stereochemistry of SN1 reactions Reactions that involve racemization: Factors affecting the rates of SN1 and SN2 reaction The structure of the substrate The concentration and reactivity of the nucleophile The effect of the solvent The nature of the leaving group The effect of the structure of the substrate SN2 Reactions Simply alkyl halides show the following general order of reactivity in SN2 reactions: (steric effect) Methyl primary secondary (tertiary-unreactive) Factors favoring SN1 versus SN2 reactions Factor SN1 SN2 Sub