JEE Main 2025 · 3 April · morning · Single correct · +4 / −1

The least acidic compound, among the following is:

JEE Main PYQ figure
  1. (a) B
  2. (b) D
  3. (c) A
  4. (d) C
Answer and solution

Answer (b) D

Solution

Chemistry ma’am · 4 steps

Find the acidic H in each one. Only D has no O–H at all, just a terminal alkyne C–H.

  1. Locate the acidic H. Acidity depends on how stable the anion is after the H⁺ leaves. A, B and C each lose H⁺ from an O–H. D is an ester, HC≡C-COOC₂H₅, so its only acidic hydrogen is the one on the sp carbon of the alkyne.
  2. Oxygen versus carbon. Oxygen is far more electronegative than carbon, so it holds a negative charge much better. In B and C the charge is also spread by resonance over several oxygens, and in A it spreads over oxygen and the ring.
    CompoundAcidic HNegative charge ends up onApprox. pKₐ
    B, C₆H₅SO₃H-SO₃Hthree equivalent O atoms≈ -2.8
    C, butanoic acid-COOHtwo equivalent O atoms≈ 4.8
    A, 3-ethoxyphenolphenolic O–HO, partly delocalised into the ring≈ 9.6
    D, ethyl propiolate≡C–Hone sp carbonfar above 10
  3. Why D stays weak. The sp carbon has 50% s-character, and the ester group pulls some electron density away, so this C–H is more acidic than an ordinary C–H. A carbanion is still much less stable than any oxyanion, so D is the weakest acid of the four.
  4. So. The order is B > C > A > D. The least acidic compound is D, option (b).

The idea to keep. To rank acids, look at the conjugate base. Charge on oxygen, spread by resonance, means a strong acid. Charge on a single carbon means a very weak acid, even an sp carbon.

Answer from the NTA final answer key. Solution by PrepWiser.

Study General Organic Chemistry (GOC)

Asked about 180 times in JEE Main since 2020. This question is from 2025.