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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.
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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