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Question #44814

Difficulty: 8/10 | 🟢 Free

The Question

The aminolysis of phenyl acetate (EE) by a primary amine (AA) in an aprotic solvent at 298 K proceeds via a zwitterionic tetrahedral intermediate (T±T^{\pm}). The proposed mechanism involves the following elementary steps:

Step 1: E+A⇌T±E + A \rightleftharpoons T^{\pm} (forward rate constant k1k_1, reverse k−1k_{-1})

Step 2: T±→k2Amide+PhenolT^{\pm} \xrightarrow{k_2} \text{Amide} + \text{Phenol}

Step 3: T±+A→k3Amide+Phenol+AT^{\pm} + A \xrightarrow{k_3} \text{Amide} + \text{Phenol} + A

The experimental initial rate of amide formation is expressed as v0=kapp[E][A]v_0 = k_{app}[E][A]. Applying the steady-state approximation to T±T^{\pm}, what are the limiting values of the apparent second-order rate constant kappk_{app} at very low amine concentration ([A]→0[A] \to 0) and very high amine concentration ([A]→∞[A] \to \infty), respectively?

Options

  • A.

    k1k2k−1+k2\frac{k_1 k_2}{k_{-1} + k_2} and k1k_1

  • B.

    k1k2k−1\frac{k_1 k_2}{k_{-1}} and k1k_1

  • C.

    k1k2k−1+k2\frac{k_1 k_2}{k_{-1} + k_2} and k3k_3

  • D.

    k1k_1 and k1k3k−1+k2\frac{k_1 k_3}{k_{-1} + k_2}

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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

Rate Law Derivation from Mechanism|Steady State Approximation|Esterification Reversibility

Why This Question Is Tricky

Common Mistakes

Students often erroneously assume the first step is the rate-determining step (RDS) or that the intermediate is in rapid equilibrium with the reactants.

Assuming rapid equilibrium yields kapp=k1k−1(k2+k3[A])k_{app} = \frac{k_1}{k_{-1}}(k_2 + k_3[A]), which incorrectly predicts that the rate constant diverges to infinity at high amine concentrations.

This problem forces the use of the Steady-State Approximation (SSA) to account for the reversibility of the intermediate formation.

It highlights a critical kinetic phenomenon: at high amine concentrations, the breakdown of the intermediate becomes so fast that the initial nucleophilic attack (Step 1) becomes the true rate-determining step, capping the apparent rate constant at k1k_1.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterChemical Kinetics - Class 12
ConceptRate Law Derivation from Mechanism
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree