An SN2 reaction couples backside nucleophilic bond formation to leaving-group departure in one elementary substitution step. At a suitable stereogenic reaction centre, the geometry produces inversion.
Approach of a nucleophile opposite the leaving-group bond permits bond formation with inversion at the attacked tetrahedral carbon in an SN2 pathway.
Carbon-centred substitution in a cyclic sulfonate ester. The incoming nucleophile bonds to the oxygen-bound ring carbon and the resulting product retains the carbon–sulfur bond.
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