The least acidic compound, among the following is: [figure]
- B
- D
- A
- C
Answer
(2) D
Solution
(B) Benzenesulphonic acid: a very strong acid (pKa -2.8); the anion is strongly resonance stabilised over three O atoms.
(C) Butanoic acid: carboxylic acid (pKa 4.8); the carboxylate ion is resonance stabilised over two O atoms.
(A) 3-Ethoxyphenol: a phenol (pKa 10); the phenoxide ion is stabilised by delocalisation into the ring.
(D) Ethyl propiolate: only the ≡C–H hydrogen is acidic; the negative charge stays on an sp carbon (pKa of a terminal alkyne is above 20, even with the -CO2Et group).
Acidic strength: B > C > A > D D is the least acidic.
Answer: (2)