The lower the pKa of the conjugate acid, the better the leaving group, because then they can easily stabilize the developing negative charge. SN1 reactions prefer halide ions as leaving groups.
In room-temperate water, the sequence of lability is:
During the SN2[?] nucleophilic attack[?], a partial negative charge forms on the leaving group. During SN1 reactions, the leaving group anionizes and leaves.
In the non-mechanistic transformations, leaving group is the actual substituent group present in the substrate and product.
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