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Question #44825

Difficulty: 8/10 | 🟢 Free

The Question

The keto-enol tautomerization of Uracil (UU) in a mixed solvent system containing water (WW) and an inert diluent proceeds via a solvent-bridged intermediate (II). The proposed mechanism is:

Step 1: \ceU+W<=>[k1][k−1]I\ce{U + W <=>[k_1][k_{-1}] I} Step 2: \ceI+W−>[k2]E+2W\ce{I + W ->[k_2] E + 2W} (where EE is the enol form)

The Arrhenius parameters for the elementary steps at 300 K300\text{ K} are given below: A1=1011 M−1s−1A_1 = 10^{11}\text{ M}^{-1}\text{s}^{-1}, Ea1=15.0 kJ/molE_{a1} = 15.0\text{ kJ/mol} A−1=1012 s−1A_{-1} = 10^{12}\text{ s}^{-1}, Ea,−1=28.5 kJ/molE_{a,-1} = 28.5\text{ kJ/mol} A2=1014 M−1s−1A_2 = 10^{14}\text{ M}^{-1}\text{s}^{-1}, Ea2=40.0 kJ/molE_{a2} = 40.0\text{ kJ/mol}

Applying the steady-state approximation to [I][I], the reaction exhibits a change in kinetic order with respect to [W][W] depending on the solvent composition. Determine the transition concentration [W]trans[W]_{trans} at which the rate of dissociation of II equals its rate of forward reaction to EE. Furthermore, calculate the apparent activation energy (Ea,obsE_{a,obs}) of the overall tautomerization when [W]≪[W]trans[W] \ll [W]_{trans}.

(Given: 2.303RT=5.75 kJ/mol2.303 RT = 5.75\text{ kJ/mol} at 300 K300\text{ K})

Options

  • A.

    [W]trans=1.0 M[W]_{trans} = 1.0\text{ M}, Ea,obs=26.5 kJ/molE_{a,obs} = 26.5\text{ kJ/mol}

  • B.

    [W]trans=0.1 M[W]_{trans} = 0.1\text{ M}, Ea,obs=55.0 kJ/molE_{a,obs} = 55.0\text{ kJ/mol}

  • C.

    [W]trans=10.0 M[W]_{trans} = 10.0\text{ M}, Ea,obs=15.0 kJ/molE_{a,obs} = 15.0\text{ kJ/mol}

  • D.

    [W]trans=1.0 M[W]_{trans} = 1.0\text{ M}, Ea,obs=11.5 kJ/molE_{a,obs} = 11.5\text{ kJ/mol}

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Mechanism_Trap

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Concepts Behind This Question

Collision Frequency vs. Effective Collisions|Nitrogenous Base Keto-Enol Tautomerism|Steady State Approximation

Why This Question Is Tricky

Common Mistakes

This problem tests the intersection of Collision Theory and the Steady-State Approximation in the context of solvent-assisted tautomerization.

Students often assume that high collision frequencies directly dictate the rate-determining step.

However, the strict geometric requirement for the proton relay (Step 2) imposes a high activation energy (Ea2E_{a2}), making the intermediate highly susceptible to dissociation (k−1k_{-1}) at low water concentrations.

The 'Hidden Variable' is the solvent concentration acting as both a reactant and a kinetic switch.

By changing [W][W], the steady-state concentration of the enol precursor shifts, masking the true molecularity and altering the apparent activation energy from Ea1+Ea2−Ea,−1E_{a1} + E_{a2} - E_{a,-1} (at low [W][W]) to simply Ea1E_{a1} (at high [W][W]).

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Question Information

SubjectChemistry
ChapterChemical Kinetics - Class 12
ConceptCollision Frequency vs. Effective Collisions
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree