JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
The increasing order of for the following phenols is (A) 2, 4 - Dinitrophenol (B) 4 - Nitrophenol (C) 2, 4, 5 - Trimethylphenol (D) Phenol (E) 3-Chlorophenol Choose the correct answer from the option given below :
- A(A), (E), (B), (D), (C)
- B(C), (E), (D), (B), (A)
- C(C), (D), (E), (B), (A)
- D(A), (B), (E), (D), (C)
View written solutionFree
Correct answer: D
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Concept used: Lower means stronger acid.
For phenols:
- Electron-withdrawing groups (EWG) increase acidity by stabilizing the phenoxide ion, so they decrease .
- Electron-donating groups (EDG) decrease acidity by destabilizing the phenoxide ion, so they increase .
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Analyze each compound:
(A) 2,4-Dinitrophenol
- Has two nitro groups, both strongly electron-withdrawing by and effects.
- This strongly stabilizes the phenoxide ion.
- Hence it is the most acidic and has the lowest .
(B) 4-Nitrophenol
- One nitro group at para position.
- Strong EWG, stabilizes phenoxide by resonance.
- More acidic than phenol.
(E) 3-Chlorophenol
- Chlorine shows effect (electron-withdrawing), which increases acidity.
- At meta position, resonance interaction with the phenoxide ion is not effective, so mainly inductive effect operates.
- Thus it is more acidic than phenol, but less acidic than p-nitrophenol.
(D) Phenol
- Reference compound.
(C) 2,4,5-Trimethylphenol
- Three methyl groups are electron-donating by effect and hyperconjugation.
- They destabilize the phenoxide ion.
- Hence this is the least acidic and has the highest .
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Therefore, acidity order is:
Since increasing is opposite to acidity order,
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Match with options:
This corresponds to:
So the correct option is D.
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Comparison with stored answer:
Stored correct answer = D.
My derived answer also = D.
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