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Question #44061

Difficulty: 8/10 | 🟢 Free

The Question

The formation of the Wheland intermediate (σ\sigma-complex) during the electrophilic aromatic substitution of 1,3,5-trimethoxybenzene (TMB) with tropylium tetrafluoroborate (\ceC7H7+BF4−\ce{C7H7+ BF4-}) is an equilibrium-controlled process:

\ceTMB+C7H7+<=>σ−complex+\ce{TMB + C7H7+ <=> \sigma-complex+}

In 1,2-dichloroethane (DCE, a non-polar solvent), the equilibrium constant is K1=0.1K_1 = 0.1 at 298 K. When the solvent is changed to acetonitrile (MeCN, a polar aprotic solvent), the σ\sigma-complex and the transition state (TS‡TS^\ddagger) are significantly stabilized by solvation. The transfer free energies from DCE to MeCN are ΔGtr(σ+)=−22.8 kJ/mol\Delta G_{tr}(\sigma^+) = -22.8 \text{ kJ/mol} and ΔGtr(TS‡)=−11.4 kJ/mol\Delta G_{tr}(TS^\ddagger) = -11.4 \text{ kJ/mol}.

Assuming the transfer free energies of the neutral TMB and the large, diffuse \ceC7H7+\ce{C7H7+} cation are negligible (≈0\approx 0), calculate the equilibrium constant K2K_2 and the ratio of the forward rate constants (kf2/kf1k_{f2}/k_{f1}) in MeCN at 298 K.

(Given: 2.303RT=5.7 kJ/mol2.303 RT = 5.7 \text{ kJ/mol} at 298 K)

Options

  • A.

    K2=103K_2 = 10^3, kf2/kf1=102k_{f2}/k_{f1} = 10^2

  • B.

    K2=104K_2 = 10^4, kf2/kf1=102k_{f2}/k_{f1} = 10^2

  • C.

    K2=103K_2 = 10^3, kf2/kf1=104k_{f2}/k_{f1} = 10^4

  • D.

    K2=10−5K_2 = 10^{-5}, kf2/kf1=10−2k_{f2}/k_{f1} = 10^{-2}

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Correct Answer

Step-by-Step Solution

Explanation

How the Examiner Thinks

Exception_Exposure

Learn to identify edge cases and boundary exceptions that JEE examiners hide in math problems.

Concepts Behind This Question

Reaction Quotient vs. Equilibrium Constant|Solvent Effects on Reactivity|Electrophilic Substitution Activation/Deactivation

Why This Question Is Tricky

Common Mistakes

This question tests the 'Hidden Variable' of solvent-induced thermodynamic and kinetic shifts in electrophilic aromatic substitution.

Students typically memorize that EAS is kinetically controlled and assume KeqK_{eq} is an intrinsic property of the electrophile and the aromatic ring.

The trap exposes the failure to differentiate between the solvation of the Transition State (which dictates the kinetic rate enhancement, kfk_f) and the solvation of the Wheland intermediate (which dictates the thermodynamic equilibrium shift, KeqK_{eq}).

By providing transfer free energies (ΔGtr\Delta G_{tr}), the problem forces the application of thermodynamic cycles to a real physical organic scenario, penalizing those who confuse ΔG∘\Delta G^\circ with ΔG‡\Delta G^\ddagger or misapply the sign conventions of stabilization energy.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterEquilibrium - Class 11 Part 1
ConceptReaction Quotient vs. Equilibrium Constant
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree