SN2 Reaction: Benzyl Chloride with HS

Picture displaying SN2 reaction

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

The π framework of p orbitals provide stabilisation in the transition state. This improves the rate of the SN2 reaction and also causes the SN2 reaction to be favoured over SN1.

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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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