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Question #44449
The Question
The absolute difference in activation energies, , for the reaction of methyl tosylate (\ce{CH3OTs}) with \ce{F^-} and \ce{I^-} is measured in two different solvents at .
In Methanol (\ce{CH3OH}), . In Dimethyl Sulfoxide (DMSO), .
Assume the Arrhenius pre-exponential factor () is identical for all four reactions. It is given that the rate constant for the reaction with \ce{I^-} in DMSO is times the rate constant for the reaction with \ce{F^-} in Methanol ().
Calculate the ratio .
(Given: )
Options
- A.
- B.
- C.
- D.
Check Your Answer
Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Mechanism_Trap
Don't get tricked by the process! Learn the mechanical traps used in competitive exam questions.
Concepts Behind This Question
Solvent Effects on Reactivity|Basicity-Solvation Competition|Reaction Intermediates Stability
Why This Question Is Tricky
Common Mistakes
The question tests the 'Solvation Competition' exception in Nucleophilic Substitution.
Students often memorize that basicity dictates nucleophilicity (F- > I-).
However, in polar protic solvents (Methanol), the high charge density of F- leads to a strong hydrogen-bonded solvation shell, creating a massive kinetic barrier for desolvation and inverting the nucleophilicity trend (I- > F-).
In polar aprotic solvents (DMSO), this shell is absent, and the trend reverts to basicity.
The trap is set by providing absolute differences in activation energies (|ΔEa|); failing to correctly assign the sign of ΔEa based on the solvent-dependent nucleophilicity inversion leads directly to the distractor options.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Organic Chemistry – Some Basic Principles and Techniques - Class 11 Part 2 |
| Concept | Solvent Effects on Reactivity |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |