Nucleophilic Substitution at Saturated Carbon: SN2 Reactions


SN2 reactions are one particular type of nucleophilic substitution where the rate is determined by both the nucleophile and the substrate. They usually have an unhindered substrate (primary or secondary), a strong nucleophile, and a good leaving group. There is also usually inversion of the stereochemistry at the carbon where the substitution takes place.

SN2 mechanisms

Click each reaction to view the associated 3D animations

R. H. DeWolfe and W. G. Young, Chem. Rev., 1956, 56, 753–901.

J. W. Hill and A. Fry, J. Am. Chem. Soc., 1962, 84, 2763–2769.

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