JEE Main 2024 · 9 April · morning · Single correct · +4 / −1
For the given compounds, the correct order of increasing pKₐ value :
Choose the correct answer from the options given below :
- (a) (E) <(D)<(C)<(B)<(A)
- (b) (B) <(D)<(A)<(C)<(E)
- (c) (D) < (E) < (C) < (B) < (A)
- (d) (E) <(D)<(B)<(A)<(C)
Answer and solution
Answer (b) (B) <(D)<(A)<(C)<(E)
Solution
Chemistry ma’am · 3 steps
Lower pKa means stronger acid, so rank by how well each group stabilises the phenoxide ion.
- What decides pKa. Phenol loses H⁺ to give a phenoxide ion. A group that pulls electron density away spreads the negative charge and stabilises the ion, so the acid is stronger and its pKa is lower. A group that pushes electrons in does the reverse.
- Position matters. Resonance effects act only from the ortho and para positions. From the meta position a group acts mainly through its weaker inductive effect. So a group at para has a bigger effect than the same group at meta, in whichever direction it pushes.
Compound Group and position Effect on phenoxide pKa (B) -NO₂, para −R and −I, strongly stabilises lowest (D) -NO₂, meta −I only, stabilises less low (A) none reference middle (C) -OCH₃, meta no +R from meta, small effect high (E) -OCH₃, para +R pushes charge onto the ring, destabilises most highest - So. Increasing pKa runs from the strongest acid to the weakest: (B) < (D) < (A) < (C) < (E), which is option (b).
The idea to keep. Electron-withdrawing groups lower pKa and electron-donating groups raise it. The effect is strongest at para (resonance plus induction) and weaker at meta (induction alone).
Answer from the NTA final answer key. Solution by PrepWiser.