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Question #44402
The Question
An organic salt, -(2-bromoethyl)anilinium bromide (1.0 equivalent), is treated with exactly 1.0 equivalent of sodium ethoxide (\ce{NaOEt}) in absolute ethanol (\ce{EtOH}) at 298 K. The reaction mixture is stirred for a short duration. Which of the following represents the major organic species present in the reaction mixture?
Options
- A.
-(2-ethoxyethyl)anilinium bromide
- B.
1-phenylaziridine
- C.
-(2-bromoethyl)aniline
- D.
-vinylaniline
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
Williamson Ether Synthesis Constraints|Basicity-Solvation Competition|Aniline Resonance Pitfalls
Why This Question Is Tricky
Common Mistakes
This problem tests the kinetic supremacy of acid-base neutralization over bimolecular nucleophilic substitution (Williamson ether synthesis) and the stereoelectronic impact of resonance on nucleophilicity.
The primary trap is the 'Aniline Resonance Pitfall'.
Students often assume the alkoxide will act as a nucleophile to form an ether, ignoring the acidic proton.
Alternatively, if they recognize the acid-base step, they falsely assume the resulting free amine will rapidly cyclize into an aziridine (like an aliphatic amine would).
The hidden variable is the stoichiometric exhaustion of the base combined with the resonance-deactivated nucleophile, which kinetically stalls the synthesis at the free base at room temperature.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Alcohols, Phenols, and Ethers - Class 12 |
| Concept | Williamson Ether Synthesis Constraints |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |