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Alcohols Phenols and Ethers question

2024 · 29 Jan · Shift 2 · Q18
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Alcohols Phenols and Ethers question

2024 · 29 Jan · Shift 2 · Q18

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1

Match List I with List II

List - I
(Compound)
List - II
(pKa\mathrm{pK_a}pKa​ value)
(A) Ethanol (I) 10.0
(B) Phenol (II) 15.9
(C) m-Nitrophenol (III) 7.1
(D) p-Nitrophenol (IV) 8.3

Choose the correct answer from the options given below:

  1. A
    A-I, B-II, C-III, D-IV
  2. B
    A-IV, B-I, C-II, D-III
  3. C
    A-II, B-I, C-IV, D-III
  4. D
    A-III, B-IV, C-I, D-II
View written solutionFree

Correct answer: C

  1. Recall approximate pKa\mathrm{p}K_apKa​ values of the given compounds.

    • Ethanol is a simple alcohol, so it is much less acidic than phenols. pKa(ethanol)≈15.9\mathrm{p}K_a(\text{ethanol}) \approx 15.9pKa​(ethanol)≈15.9

    • Phenol is more acidic than ethanol because the phenoxide ion is resonance-stabilized. pKa(phenol)≈10.0\mathrm{p}K_a(\text{phenol}) \approx 10.0pKa​(phenol)≈10.0

    • Nitrophenols are more acidic than phenol because the −NO2-\mathrm{NO_2}−NO2​ group is electron-withdrawing and stabilizes the phenoxide ion.

  2. Compare mmm-nitrophenol and ppp-nitrophenol.

    • In ppp-nitrophenol, the −NO2-\mathrm{NO_2}−NO2​ group exerts both −I-I−I and −R-R−R effects, giving stronger stabilization of the conjugate base.
    • In mmm-nitrophenol, only the −I-I−I effect operates significantly; resonance stabilization of the negative charge is not effective at meta position.

    Therefore, p-nitrophenol is more acidic than m-nitrophenol\text{$p$-nitrophenol is more acidic than $m$-nitrophenol}p-nitrophenol is more acidic than m-nitrophenol so it must have the lower pKa\mathrm{p}K_apKa​.

  3. Match with the given values:

    Given values are: (I)  10.0,(II)  15.9,(III)  7.1,(IV)  8.3\text{(I)}\;10.0,\quad \text{(II)}\;15.9,\quad \text{(III)}\;7.1,\quad \text{(IV)}\;8.3(I)10.0,(II)15.9,(III)7.1,(IV)8.3

    So,

    • Ethanol →15.9\to 15.9→15.9 ⇒\Rightarrow⇒ A-II
    • Phenol →10.0\to 10.0→10.0 ⇒\Rightarrow⇒ B-I
    • mmm-Nitrophenol →8.3\to 8.3→8.3 ⇒\Rightarrow⇒ C-IV
    • ppp-Nitrophenol →7.1\to 7.1→7.1 ⇒\Rightarrow⇒ D-III
  4. Final matching: A−II,  B−I,  C−IV,  D−IIIA-\mathrm{II},\;B-\mathrm{I},\;C-\mathrm{IV},\;D-\mathrm{III}A−II,B−I,C−IV,D−III

  5. Check options:

    This corresponds to Option C.

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