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In which of the following reactions, SN^...

In which of the following reactions, `SN^2` rate increases on changing the solvent from (95 % acetone + 5 % `H_2 O`) to (80 % acetone + 20 % `H_2O`) ?

A

`Me_2 - overset (oplus) P- Me + NH_3 rarr Me overset (oplus) N H_3 + Me_2 P`

B

`MeI + PH_3 rarr Me overset (oplus) P H_3 + I^(Ө)`

C

`MeBr + overset (Ө) O H rarr MeOH + Br^(Ө)`

D

`Me_2 - overset (oplus) S - Me + overset (Ө)OH rarr MeOH + Me_2 S`

Text Solution

AI Generated Solution

The correct Answer is:
To determine in which of the following reactions the SN2 rate increases when changing the solvent from 95% acetone + 5% water to 80% acetone + 20% water, we need to analyze the effect of solvent polarity on the SN2 reaction mechanism. ### Step-by-Step Solution: 1. **Understanding SN2 Mechanism**: - The SN2 (Substitution Nucleophilic Bimolecular) reaction involves a nucleophile attacking an electrophile, leading to the substitution of one group for another. The rate of an SN2 reaction depends on both the nucleophile and the substrate. 2. **Effect of Solvent on SN2 Reactions**: - The solvent can affect the rate of the reaction by stabilizing or destabilizing the reactants and transition states. - In a polar solvent, charged species (like nucleophiles or electrophiles) are stabilized due to solvation, which can slow down the reaction if the reactants are charged. 3. **Changing Solvent Composition**: - By changing the solvent from 95% acetone (a polar aprotic solvent) + 5% water to 80% acetone + 20% water, we are increasing the polarity of the solvent mixture. - Increasing the proportion of water (which is a polar protic solvent) increases the overall polarity of the solvent. 4. **Analyzing Reactants**: - If the reactants are charged (e.g., a nucleophile like OH⁻), increasing solvent polarity will stabilize the charged reactants, thus decreasing the reaction rate. - If the reactants are neutral, increasing the solvent polarity will stabilize the transition state, which can increase the reaction rate. 5. **Conclusion**: - Based on the above analysis, the SN2 reaction rate will increase when the reactants are neutral and the solvent polarity is increased. - Therefore, we need to identify the reaction among the options provided where the reactants are neutral. ### Final Answer: The correct answer is **B**, where the SN2 reaction rate increases upon changing the solvent from 95% acetone + 5% water to 80% acetone + 20% water.
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CENGAGE CHEMISTRY ENGLISH-ORGANIC REACTION MECHANISM-Single correct
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