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Alcohols Phenols and Ethers question

2023 · 29 Jan · Shift 1 · Q9
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  5. /2023 · 29 Jan · Shift 1 · Q9

Alcohols Phenols and Ethers question

2023 · 29 Jan · Shift 1 · Q9

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
The increasing order of pKa\mathrm{pK_a}pKa​ 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 :
  1. A
    (A), (E), (B), (D), (C)
  2. B
    (C), (E), (D), (B), (A)
  3. C
    (C), (D), (E), (B), (A)
  4. D
    (A), (B), (E), (D), (C)
View written solutionFree

Correct answer: D

  1. Concept used: Lower pKa\mathrm{p}K_apKa​ means stronger acid.

    For phenols:

    • Electron-withdrawing groups (EWG) increase acidity by stabilizing the phenoxide ion, so they decrease pKa\mathrm{p}K_apKa​.
    • Electron-donating groups (EDG) decrease acidity by destabilizing the phenoxide ion, so they increase pKa\mathrm{p}K_apKa​.
  2. Analyze each compound:

    (A) 2,4-Dinitrophenol

    • Has two nitro groups, both strongly electron-withdrawing by −I-I−I and −M-M−M effects.
    • This strongly stabilizes the phenoxide ion.
    • Hence it is the most acidic and has the lowest pKa\mathrm{p}K_apKa​.

    (B) 4-Nitrophenol

    • One nitro group at para position.
    • Strong EWG, stabilizes phenoxide by resonance.
    • More acidic than phenol.

    (E) 3-Chlorophenol

    • Chlorine shows −I-I−I 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 +I+I+I effect and hyperconjugation.
    • They destabilize the phenoxide ion.
    • Hence this is the least acidic and has the highest pKa\mathrm{p}K_apKa​.
  3. Therefore, acidity order is:

    A>B>E>D>CA > B > E > D > CA>B>E>D>C

    Since increasing pKa\mathrm{p}K_apKa​ is opposite to acidity order,

    A<B<E<D<C\boxed{A < B < E < D < C}A<B<E<D<C​

  4. Match with options:

    This corresponds to:

    (A),(B),(E),(D),(C)\boxed{(A), (B), (E), (D), (C)}(A),(B),(E),(D),(C)​

    So the correct option is D.

  5. Comparison with stored answer:

    Stored correct answer = D.

    My derived answer also = D.

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