JEE Main 2023 · 13 April · evening · Single correct · +4 / −1

Given below are two statements, one is labelled as Assertion A and the other is labelled as Reason R.
Assertion A : Order of acidic nature of the following compounds is A > B > C.
Reason R : Fluoro is a stronger electron withdrawing group than Chloro group.
In the light of the above statements, choose the correct answer from the options given below:

JEE Main PYQ figure
  1. (a) Both A and R are correct but R is NOT the correct explanation of A
  2. (b) A is false but R is true
  3. (c) A is true but R is false
  4. (d) Both A and R are correct and R is the correct explanation of A
Answer and solution

Answer (a) Both A and R are correct but R is NOT the correct explanation of A

Solution

Chemistry ma’am · 5 steps

Both statements are true, but if fluorine's pull decided it, B would beat A. Position wins here.

  1. Read the compounds. The rings are benzene rings, so all three are phenols. A is 2-chlorophenol, B is 4-fluorophenol and C is 3-methylphenol (m-cresol).
  2. What sets acidity. A phenol is more acidic when its phenoxide ion is more stable. Electron-withdrawing effects near the oxygen stabilise the ion. Electron-donating effects destabilise it.
    PhenolEffect on the phenoxideApprox. pKₐ
    A: ortho-ClStrong -I, acting from very close to the O8.5, most acidic
    B: para-FWeak -I from far away, largely cancelled by strong +R (2p–2p overlap)9.9
    C: meta-CH₃+I donates electrons, so the ion is destabilised10.1, least acidic
  3. Check each statement. So A > B > C, and Assertion A is true. Fluorine is more electronegative than chlorine, so it withdraws more strongly by induction, and Reason R is true.
  4. Does R explain A. No. If fluorine's stronger pull decided the order, B would be more acidic than A. A wins because chlorine sits at the ortho position, close to the O–H, while para-fluorine also gives electrons back by +R.
  5. So. Both A and R are correct, but R is not the correct explanation of A. The answer is (a).

The idea to keep. For substituted phenols, check the position before the electronegativity. Ortho -I acts right next to the O–H. A para halogen also pushes electrons back by +R, and fluorine's +R is strong.

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

Study Alcohols, Phenols & Ethers

Asked about 110 times in JEE Main since 2020. This question is from 2023.