JEE Main 2025 · 3 April · morning · Single correct · +4 / −1
The least acidic compound, among the following is:
- (a) B
- (b) D
- (c) A
- (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.
- 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.
- 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.
Compound Acidic H Negative charge ends up on Approx. pKₐ B, C₆H₅SO₃H -SO₃H three equivalent O atoms ≈ -2.8 C, butanoic acid -COOH two equivalent O atoms ≈ 4.8 A, 3-ethoxyphenol phenolic O–H O, partly delocalised into the ring ≈ 9.6 D, ethyl propiolate ≡C–H one sp carbon far above 10 - 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.
- 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.