Question:

For the given compounds, the correct order of increasing \(pK_a\) value :
Chemical compounds

Updated On: Nov 23, 2024
  • \((E)<(D)<(C)<(B)<(A)\)

  • \((D)<(E)<(C)<(B)<(A)\)

  • \((E)<(D)<(B)<(A)<(C)\)

  • \((B)<(D)<(A)<(C)<(E)\)

  • None of these
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The Correct Option is

Solution and Explanation

Explanation:

  1. Definition of \( pK_a \): Lower \( pK_a \) corresponds to a stronger acid.
  2. Factors affecting \( pK_a \):
    • Electron-withdrawing groups (EWG) increase acidity by stabilizing the conjugate base.
    • Electron-donating groups (EDG) decrease acidity by destabilizing the conjugate base.
  3. Order Analysis:
    • (D) Dinitrophenol: Strongest acid due to two nitro (EWG) groups stabilizing the phenoxide ion.
    • (B) Nitrophenol: Less acidic than (D), but still acidic due to one nitro group.
    • (A) Phenol: Less acidic than (B) due to the absence of strong EWGs.
    • (C) Methoxyphenol: The methoxy group (EDG) destabilizes the phenoxide ion, making it less acidic than phenol.
    • (E) Methoxy-dinitrophenol: The methoxy group reduces the effect of the nitro groups, making it less acidic than dinitrophenol but more acidic than phenol.
  4. Final Order: \[ (D) < (B) < (A) < (C) < (E). \]

Final Answer: None of these.

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