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Question #45053
The Question
Consider the reactions of 1-fluoro-2,4-dinitrobenzene (\textbf{I}) and 1-chloro-2,4-dinitrobenzene (\textbf{II}) at 298 K under two different conditions:\n\nReaction 1: \textbf{I} and \textbf{II} with in DMSO. (Second-order rate constants: and )\nReaction 2: \textbf{I} and \textbf{II} with in DMSO. (Second-order rate constants: and )\n\nLet 'Attack' denote the formation of the Meisenheimer complex and 'Cleavage' denote the breaking of the carbon-halogen bond. Which of the following correctly identifies the relative rate constants and the rate-determining step (RDS) for each reaction?
Options
- A.
(RDS: Attack) ; (RDS: Cleavage)
- B.
(RDS: Attack) ; (RDS: Attack)
- C.
(RDS: Cleavage) ; (RDS: Cleavage)
- D.
(RDS: Attack) ; (RDS: Cleavage)
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
Resonance Energy and Stability|Nucleophilic Aromatic Substitution (SNAr)|Solvent Effects on Reactivity
Why This Question Is Tricky
Common Mistakes
Students typically memorize the reactivity order as F > Cl > Br > I, assuming the nucleophilic attack is always the rate-determining step due to the temporary loss of aromaticity.
The hidden variable being tested is the steric bulk of the nucleophile.
A bulky nucleophile like introduces massive steric strain in the intermediate, making its formation highly reversible.
This shifts the RDS to the leaving group departure, completely inverting the reactivity order because the C-F bond is exceptionally strong compared to C-Cl.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Organic Chemistry – Some Basic Principles and Techniques - Class 11 Part 2 |
| Concept | Resonance Energy and Stability |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |