Nucleophilic Conjugate Substitution - The SN2' Mechanism

Reaction of a Secondary Allyl Chloride with HS -

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Picture displaying SN2 reaction

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

This subclass of nucleophilic substitution occurs when the nucleophile (HS-) attacks the alkene instead of the saturated carbon - the SN2' mechanism. This is the due to the saturated carbon being hindered (it is a secondary carbon), making the regular SN2 mechanism less favourable.

Back to more SN2 reactions

Alternatively, use these links: (Substrate: Nucleophile)

Allyl chloride : SH | Benzyl chloride : SH | 2o benzyl chloride : SH | 2o allyl chloride : SH (SN2')

Other pages of interest to do with Animated Molecular Orbitals are

Introduction to Animated Molecular Orbitals | Introductory Organic Reactions

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.