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有机化学课件 The SN2 Mechanism of Nucleophilic Substitution.ppt

有机化学课件 The SN2 Mechanism of Nucleophilic Substitution.ppt

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有机化学课件 The SN2 Mechanism of Nucleophilic Substitution

8.3 The SN2 Mechanism of Nucleophilic Substitution Kinetics Many nucleophilic substitutions follow a second-order rate law. CH3Br + HO – ? CH3OH + Br – rate = k[CH3Br][HO – ] inference: rate-determining step is bimolecular Bimolecular mechanism one step concerted Bimolecular mechanism one step concerted Bimolecular mechanism one step concerted 8.4 Stereochemistry of SN2 Reactions Generalization Nucleophilic substitutions that exhibit second-order kinetic behavior are stereospecific and proceed with inversion of configuration. Inversion of Configuration Inversion of Configuration Stereospecific Reaction A stereospecific reaction is one in which stereoisomeric starting materials give stereoisomeric products. The reaction of 2-bromooctane with NaOH (in ethanol-water) is stereospecific. (+)-2-Bromooctane ? (–)-2-Octanol (–)-2-Bromooctane ? (+)-2-Octanol Stereospecific Reaction Problem 8.4 The Fischer projection formula for (+)-2-bromooctane is shown. Write the Fischer projection of the (–)-2-octanol formed from it by nucleophilic substitution with inversion of configuration. Problem 8.4 The Fischer projection formula for (+)-2-bromooctane is shown. Write the Fischer projection of the (–)-2-octanol formed from it by nucleophilic substitution with inversion of configuration. 8.5 How SN2 Reactions Occur 8.6 Steric Effects in SN2 Reactions Crowding at the Reaction Site Table 8.2 Reactivity toward substitution by the SN2 mechanism Alkyl Class Relative bromide rate CH3Br Methyl 221,000 CH3CH2Br Primary 1,350 (CH3)2CHBr Secondary 1 (CH3)3CBr Tertiary too small to measure Decreasing SN2 Reactivity Decreasing SN2 Reactivity Crowding Adjacent to the Reaction Site Table 8.3 Effect of chain branching on rate of SN2 substitution Alkyl Structure Relative bromide rate Ethyl CH3CH2Br 1.0 Propyl CH3CH2CH2Br 0.8 Isobutyl (CH3)2CHCH2Br 0.036 Neopentyl (CH3)3CCH2Br 0.00002 25 25 24 25 29 29 30 31 31 31 HO – CH3Br + HOCH3 Br – + HO – CH3Br + HOCH3 Br – +

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