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Question #44387
The Question
Consider the bifunctional aromatic compound 4-(4-aminobenzyl)phenol. It is subjected to two separate electrophilic aromatic substitution reactions:
Reaction 1: Treatment with 1 equivalent of in at 298 K yields major product P.
Reaction 2: Treatment with 1 equivalent of conc. and conc. at 288 K, followed by mild basic neutralization, yields major product Q.
Identify the major products P and Q.
Options
- A.
P = 4-(4-amino-3-bromobenzyl)phenol ; Q = 4-(4-aminobenzyl)-2-nitrophenol
- B.
P = 4-(4-aminobenzyl)-2-bromophenol ; Q = 4-(4-amino-3-nitrobenzyl)phenol
- C.
P = 4-(4-amino-3-bromobenzyl)phenol ; Q = 4-(4-amino-3-nitrobenzyl)phenol
- D.
P = 4-(4-aminobenzyl)-2-bromophenol ; Q = 4-(4-aminobenzyl)-2-nitrophenol
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
EAS in Phenols|Electrophilic Substitution Control|Ortho-Effect in Anilines
Why This Question Is Tricky
Common Mistakes
This question tests the student's ability to dynamically evaluate relative ring activation in a multi-ring system based on the pH of the reaction medium.
The 'Textbook Rule' states that -NH2 is a stronger activator than -OH.
Students who blindly apply this rule will choose Option C.
The 'Hidden Variable' is the drastic pKa difference between the amine and the phenol.
Under strongly acidic nitration conditions, the amine is protonated to a deactivating -NH3+ group, forcing the electrophile to attack the phenol ring instead.
This perfectly illustrates reagent-controlled regioselectivity.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Alcohols, Phenols, and Ethers - Class 12 |
| Concept | EAS in Phenols |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |