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How does the nature of the leaving group affect the rate of SN1 and SN2 reactions?

Question

How does the nature of the leaving group affect the rate of SN1 and SN2 reactions?

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Solution

The nature of the leaving group significantly affects the rate of both SN1 and SN2 reactions. Here's how:

  1. Leaving Group Ability: A good leaving group is one that can stabilize the negative charge it receives after it leaves. This is usually a weak base. The better the leaving group, the faster the reaction, whether it's SN1 or SN2. This is because the leaving group is involved in the rate-determining step of both reactions.

  2. Stability of Leaving Group: In SN1 reactions, the leaving group leaves first, forming a carbocation. If the leaving group is stable on its own, it can leave more readily, speeding up the reaction. In SN2 reactions, the leaving group leaves at the same time the nucleophile attacks. A stable leaving group can handle the negative charge it receives when it leaves, which also speeds up the reaction.

  3. Polarizability: Leaving groups that are larger and more polarizable can also leave more readily because they can distribute the negative charge over a larger volume. This is particularly important in SN2 reactions, where the leaving group must leave at the same time the nucleophile attacks.

In summary, the nature of the leaving group can greatly affect the rate of SN1 and SN2 reactions. The more stable and polarizable the leaving group, the faster the reaction will be.

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