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Question #44312

Difficulty: 8/10 | 🟢 Free

The Question

Consider the following reaction sequence involving 3-methoxyphenol (Compound X\mathbf{X}): \begin{enumerate} \item X\mathbf{X} is treated with 1.01.0 equivalent of \ceEtMgBr\ce{EtMgBr} in anhydrous THF to yield a metal-phenoxide intermediate M1\mathbf{M_1}. M1\mathbf{M_1} is then heated with \ceCO2\ce{CO_2} (120∘C120^\circ\text{C}, 5 atm5\text{ atm}), followed by acidic workup, to yield major product P\mathbf{P}. \item Separately, X\mathbf{X} is treated with aqueous \ceKOH\ce{KOH} and evaporated to dryness to form salt M2\mathbf{M_2}. M2\mathbf{M_2} is heated with \ceCO2\ce{CO_2} (120∘C120^\circ\text{C}, 5 atm5\text{ atm}), followed by acidic workup, to yield major product Q\mathbf{Q}. \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 P\mathbf{P} and Q\mathbf{Q} 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 \ceK+\ce{K^+}, which follow standard thermodynamic/steric control.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterClassification of Elements and Periodicity in Properties - Class 11 Part 1
ConceptDiagonal Relationship
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree