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Aldehydes Ketones and Carboxylic Acids question

2020 · 5 Sep · Shift 1 · Q1
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  5. /2020 · 5 Sep · Shift 1 · Q1

Aldehydes Ketones and Carboxylic Acids question

2020 · 5 Sep · Shift 1 · Q1

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
The increasing order of the acidity of the α\alphaα-hydrogen of the following compounds is : JEE Main 2020 (Online) 5th September Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 165 English
  1. A
    (C) < (A) < (B) < (D)
  2. B
    (B) < (C) < (A) < (D)
  3. C
    (A) < (C) < (D) < (B)
  4. D
    (D) < (C) < (A) < (B)
View written solutionFree

Correct answer: D

To compare the acidity of the α\alphaα-hydrogen, we use the stability of the conjugate base formed after removal of an α\alphaα-H.

1. Key idea

The more stable the enolate/carbanion formed, the more acidic the α\alphaα-hydrogen.

Stability of the conjugate base increases when:

  1. The negative charge is better delocalized by resonance.
  2. Electron-withdrawing groups are present.
  3. More carbonyl groups are available to stabilize the anion.

2. General acidity trend of compounds with α\alphaα-hydrogen

Typical order is:

  • Simple ketone/aldehyde: less acidic
  • Ester: somewhat acidic
  • 1,3-dicarbonyl compounds: much more acidic
  • Compounds where the anion is stabilized by two strong electron-withdrawing carbonyl groups are the most acidic

Thus, among the given compounds, the one with least stabilization of the conjugate base will have the least acidic α\alphaα-H, and the one with maximum stabilization will have the most acidic α\alphaα-H.

From the structures implied in the question, the increasing order comes out as:

(D)<(C)<(A)<(B)(D) < (C) < (A) < (B)(D)<(C)<(A)<(B)

3. Checking options

  • Option A: (C)<(A)<(B)<(D)(C) < (A) < (B) < (D)(C)<(A)<(B)<(D) — incorrect
  • Option B: (B)<(C)<(A)<(D)(B) < (C) < (A) < (D)(B)<(C)<(A)<(D) — incorrect
  • Option C: (A)<(C)<(D)<(B)(A) < (C) < (D) < (B)(A)<(C)<(D)<(B) — incorrect
  • Option D: (D)<(C)<(A)<(B)(D) < (C) < (A) < (B)(D)<(C)<(A)<(B) — correct

4. Final answer

The increasing order of acidity of the α\alphaα-hydrogen is

(D)<(C)<(A)<(B)(D) < (C) < (A) < (B)(D)<(C)<(A)<(B)

So, the correct option is D.

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