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Mechanism of Nucleophilic Substitution

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Chemistry

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Nucleophilic substitution is the reaction of an electron pair donor (the nucleophile,Nu) with an electron pair acceptor (the electrophile). A sp3-hybridized electrophilemust have a leaving group (X) in order for the reaction to take place.Mechanism of Nucleophilic SubstitutionThe term SN2 means that two molecules are involved in the actual transition state:The departure of the leaving group occurs simultaneously with the backside attack bythe nucleophile. The SN2 reaction thus leads to a predictable configuration of thestereocenter - it proceeds with inversion (reversal of the configuration).In the SN1 reaction, a planar carbenium ion is formed first, which then reacts furtherwith the nucleophile. Since the nucleophile is free to attack from either side, thisreaction is associated with racemization.In both reactions, the nucleophile competes with the leaving group. Because of this,one must realize what properties a leaving group should have, and what constitutes agood nucleophile. For this reason, it is worthwhile to know which factors willdetermine whether a reaction follows an SN1 or SN2 pathway.Very good leaving groups, such as triflate, tosylate and mesylate ...
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