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Question #44415
The Question
Consider the organic compound , which is 5-chloro-2-(hydroxymethyl)-4-nitrophenol. undergoes the following reaction sequence:
Step 1: is treated with Lucas reagent (anhydrous and conc. ) at to yield the major product .
Step 2: is reacted with excess in at , followed by mild acidification with dilute , to yield the major product .
Identify the correct IUPAC name for the final product .
Options
- A.
5-chloro-2-(methoxymethyl)-4-nitrophenol
- B.
5-methoxy-2-(methoxymethyl)-4-nitrophenol
- C.
5-chloro-2-(hydroxymethyl)-4-nitrophenol
- D.
2-(chloromethyl)-5-methoxy-4-nitrophenol
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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
Lucas Test Logic|Nucleophilic Aromatic Substitution (SNAr)|Aryl Halide Resonance
Why This Question Is Tricky
Common Mistakes
This problem tests the intersection of chemoselectivity and a critical exception in Nucleophilic Aromatic Substitution (NAS).
The 'Hidden Variable' is the initial acid-base reaction: basic conditions () deprotonate the phenol.
The resulting phenoxide ion () is a tremendously powerful electron-donating group.
Because it is para to the nitro group, it engages in cross-conjugation, pumping electron density into the nitro group and the aromatic ring.
This completely overrides the nitro group's activating effect, rendering the aryl chloride inert to NAS.
Furthermore, the problem tests the Lucas test's chemoselectivity, requiring students to distinguish between the reactive benzylic alcohol (stabilized by the ortho-OH) and the unreactive phenolic alcohol.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Alcohols, Phenols, and Ethers - Class 12 |
| Concept | Lucas Test Logic |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |