The ascending order of acidity of -OH group in the following compounds is : [figure] Choose the correct answer from the options given below:
- (A) < (D) < (C) < (B) < (E)
- (C) < (A) < (D) < (B) < (E)
- (C) < (D) < (B) < (A) < (E)
- (A) < (C) < (D) < (B) < (E)
Answer
(4) (A) < (C) < (D) < (B) < (E)
Solution
Acidity ∝ stability of the conjugate base (RO- / ArO-):
(A): Bu–O⁻ has no resonance, +I of butyl ⇒ (A) least acidic (pKa ≈ 16)
(C): –OMe at p gives +R ⇒ destabilises phenoxide ⇒ (C) below phenol (10.2)
(D): phenoxide resonance stabilised ⇒ (D) phenol (10.0)
(B): one p-NO2 (−R, −I) ⇒ (B) more acidic (7.1)
(E): two NO2 (o and p) ⇒ (E) most acidic (4.0)
∴ (A) < (C) < (D) < (B) < (E)
Answer: (4)