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Question #44312
The Question
Consider the following reaction sequence involving 3-methoxyphenol (Compound ): \begin{enumerate} \item is treated with equivalent of in anhydrous THF to yield a metal-phenoxide intermediate . is then heated with (, ), followed by acidic workup, to yield major product . \item Separately, is treated with aqueous and evaporated to dryness to form salt . is heated with (, ), followed by acidic workup, to yield major product . \end{enumerate} Given the diagonal relationship between Mg and Li, which strongly influences the electrostatic polarization and coordination geometry of the intermediates, identify the IUPAC names of major products and respectively.
Options
- A.
2-hydroxy-6-methoxybenzoic acid and 4-hydroxy-2-methoxybenzoic acid
- B.
4-hydroxy-2-methoxybenzoic acid and 2-hydroxy-6-methoxybenzoic acid
- C.
2-hydroxy-4-methoxybenzoic acid and 4-hydroxy-2-methoxybenzoic acid
- D.
2-hydroxy-6-methoxybenzoic acid and 2-hydroxy-4-methoxybenzoic acid
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
Diagonal Relationship|Phenol Acidity vs. Substituents|Resonance Stability Criteria
Why This Question Is Tricky
Common Mistakes
The question tests a 'Chemical Exception' where electrostatic polarization and chelation override standard steric and resonance rules.
Students typically learn that electrophilic aromatic substitution avoids sterically hindered positions (like C2 between two substituents).
However, the hidden variable is the 'Diagonal Relationship' between Mg and Li—both possess high charge densities that enable rigid multi-dentate chelation.
This chelation creates a pre-organized transition state that forces intramolecular delivery of the electrophile to the most hindered position, completely reversing the expected regioselectivity seen with non-chelating ions like , which follow standard thermodynamic/steric control.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Classification of Elements and Periodicity in Properties - Class 11 Part 1 |
| Concept | Diagonal Relationship |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |