Before You Begin
Question #44388
The Question
Consider the following reaction sequence starting from 2,6-dimethylphenol: Identify the correct IUPAC name of the final major product .
Options
- A.
2-(bromomethyl)-1,4-dimethoxy-6-methylbenzene
- B.
1-(bromomethyl)-2-methoxy-3-(methoxymethyl)benzene
- C.
2-(bromomethyl)-4-chloro-1-methoxy-6-methylbenzene
- D.
3-bromo-1,4-dimethoxy-2,6-dimethylbenzene
Check Your Answer
Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Exception_Exposure
Learn to identify edge cases and boundary exceptions that JEE examiners hide in math problems.
Concepts Behind This Question
EAS in Phenols|Oxidation State Traps|Reduction Selectivity (Sn/HCl vs LiAlH4)
Why This Question Is Tricky
Common Mistakes
The core trap tests the student's ability to recognize the 'Oxidation State Trap' in highly activated aromatic systems.
Students mechanically apply the Etard reaction () to the benzylic methyl groups, falsely identifying as a benzaldehyde derivative (leading to Option B).
Alternatively, they assume standard Electrophilic Aromatic Substitution (chlorination, leading to Option C).
The hidden variable is the competitive oxidation rate (), where the electrophilic oxidant preferentially attacks the electron-rich phenolic ring to form a quinone, completely altering the subsequent reaction pathway.
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 |