Sn2 Reactions and Solvent characteristics

In summary, the rate of SN2 reactions is fastest when the solvent has moderate polarity if the nucleophile and/or electrophile have a formal charge, but when both are neutral, the reaction rate is fastest with a highly polar solvent. This is because a polar solvent stabilizes the transition state, which contains a significant charge, resulting in a lower activation energy for the rate-determined step and thus a faster reaction rate.
  • #1
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I am having trouble figuring out why this statement is true, especially the bolded sentence:

"When the nucleophile and/or electrophile have a formal charge, SN2 reaction rate is fastest when the solvent is of modest polarity. When the nucelophile and electrophile are both neutral, SN2 reaction rate is fastest when the solvent is highly polar."
 
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  • #2
Look at it this way: we have situation when both reagents and products are neutral and thus destabilized by the charged solvent (green line). The transition state, on the other hand, where there is a significant charge is present is stabilized by polar solvent, so reaction goes faster, because activation energy for the rate determined step is decreased.
 

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1. What is an Sn2 reaction?

An Sn2 reaction, or nucleophilic substitution reaction, is a type of chemical reaction where an atom or group of atoms (the nucleophile) replaces a leaving group on a substrate molecule. This reaction follows a one-step mechanism and involves a backside attack of the nucleophile on the substrate.

2. What are the key characteristics of Sn2 reactions?

Sn2 reactions are characterized by a strong nucleophile, a good leaving group, and a polar aprotic solvent. They also follow second-order kinetics, meaning the rate of the reaction is dependent on both the concentration of the substrate and the nucleophile.

3. What is the role of solvent in Sn2 reactions?

The solvent plays a crucial role in Sn2 reactions. It must be polar to solvate the reactants, but aprotic to prevent the nucleophile from being protonated. This allows for a strong nucleophile to attack the substrate without interference from the solvent.

4. How do solvent characteristics affect Sn2 reactions?

The choice of solvent can significantly impact the rate and outcome of an Sn2 reaction. A polar solvent can stabilize the transition state and increase the reaction rate, while aprotic solvents can decrease the steric hindrance and improve the nucleophile's ability to attack the substrate.

5. What are some examples of solvents used in Sn2 reactions?

Some common solvents used in Sn2 reactions include polar aprotic solvents such as dimethyl sulfoxide (DMSO), acetone, and acetonitrile. These solvents are often used in organic chemistry reactions due to their ability to dissolve polar compounds and not interfere with the reaction mechanism.

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