Leaving group

From Academic Kids

A leaving group is an atom or molecule that detaches from an organic molecule, which, after detachment, is called the residual or main part. The ability for a functional group to leave is called lability. Leaving groups affect the intrinsic reactivity, not the nucleophilic discrimination factors.

The lower the pKa of the conjugate acid, the better the leaving group, because then they can easily stabilize the developing negative charge. Conversely, a strong base is a poor leaving group. SN1 reactions prefer halide ions as leaving groups.

In room temperature 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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