Click the structures and reaction arrows in sequence to view the 3D models and animations respectively
The π framework of p orbitals provides stabilisation in the transition state. This improves the rate of the SN2 reaction and also causes the SN2 reaction to be favoured over SN1.
Alternatively, use these links: (Substrate: Nucleophile)
Allyl chloride : SH | Benzyl chloride : SH | 2o benzyl chloride : SH | 2o allyl chloride : SH (SN2′)
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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