Polar aprotic solvent sn2 rate

In summary, a polar aprotic solvent is a type of solvent with high polarity that does not have hydrogen atoms bonded to the electronegative atom. The SN2 reaction is a type of organic chemistry reaction where a nucleophile attacks an electrophilic center, resulting in the displacement of a leaving group. Polar aprotic solvents tend to increase the rate of SN2 reactions by stabilizing the transition state. Examples of polar aprotic solvents include dimethyl sulfoxide (DMSO), dimethylformamide (DMF), acetonitrile, and acetone. However, using polar aprotic solvents in SN2 reactions can also have limitations, such as side reactions and substrate compatibility issues.
  • #1
fish
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In a Finkelstein rxn, if more acetone is added so that the total volume of the solution is doubled, would the reaction be faster or slower and by how much?

Polar aprotic solvents (like acetone) increase the rate of SN2 reactions by dissolving the ionic nucleophile and yet not solvating the nucleophile by H-bonding.

k = [substrate] [nucleophile]

so would the reaction increase by twice as much?
 
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  • #2
Well, look at your equation for k, what changes by doubling the amount of solvent?
 
  • #3


In theory, doubling the volume of the solution by adding more acetone would increase the rate of the Finkelstein reaction by a factor of two. This is because the rate of an SN2 reaction is directly proportional to the concentration of both the substrate and the nucleophile. By doubling the volume, the concentration of both the substrate and the nucleophile would also double, resulting in a faster reaction rate. However, it is important to note that in practice, other factors such as temperature, solvent polarity, and steric hindrance may also affect the reaction rate. Therefore, the increase in reaction rate may not be exactly twice as much, but it would still be significantly faster than the original reaction rate.
 

FAQ: Polar aprotic solvent sn2 rate

What is a polar aprotic solvent?

A polar aprotic solvent is a type of solvent that has a high polarity, meaning it has a strong separation of electrical charges within the molecule. However, unlike polar protic solvents, aprotic solvents do not have hydrogen atoms bonded directly to the electronegative atom.

What is the SN2 reaction?

The SN2 (substitution nucleophilic bimolecular) reaction is a type of reaction in organic chemistry where a nucleophile attacks an electrophilic center, resulting in the displacement of a leaving group. This reaction typically takes place in one step and involves the inversion of stereochemistry.

How does polar aprotic solvent affect the SN2 reaction rate?

Polar aprotic solvents tend to increase the rate of SN2 reactions by stabilizing the transition state. This is because the high polarity of the solvent helps to solvate the reactants and lowers the energy barrier for the reaction to occur.

What are some examples of polar aprotic solvents?

Examples of polar aprotic solvents include dimethyl sulfoxide (DMSO), dimethylformamide (DMF), acetonitrile, and acetone.

What are the limitations of using polar aprotic solvents in SN2 reactions?

While polar aprotic solvents can increase the rate of SN2 reactions, they can also lead to side reactions, such as elimination reactions. Additionally, some substrates may not be compatible with polar aprotic solvents, and the solvent may also affect the selectivity of the reaction.

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