The descending order of acidity among the following compounds is : [figure] Choose the correct answer from the options given below :
- B > D > E > A > C
- D > B > E > A > C
- C > A > B > D > E
- D > E > B > A > C
Answer
(4) D > E > B > A > C
Solution
Carboxylic acids are stronger than phenols: in a carboxylate ion the negative charge is spread over two equivalent, electronegative O atoms.
Acids: −NO2 (−I, −R) stabilises the carboxylate ⇒ D (p-nitrobenzoic acid, pKa 3.41) > E (benzoic acid, pKa 4.19)
Phenols: −NO2 at para delocalises the negative charge of phenoxide (−R) ⇒ B (p-nitrophenol, pKa 7.1) > A (phenol, pKa 10.0)
−OCH3 at para donates electrons (+R) and destabilises phenoxide ⇒ C (p-methoxyphenol, pKa 10.2) is the weakest.
∴ D > E > B > A > C
Answer: (4)