JEE Main 2022 · 26 June · evening · Single correct · +4 / −1

The correct order of nucleophilicity is

  1. (a) F⁻ > OH⁻
  2. (b) H₂Ö > OH⁻
  3. (c) RO(··)H > RO⁻
  4. (d) NH₂⁻ > NH₃
Answer and solution

Answer (d) NH₂⁻ > NH₃

Solution

Chemistry ma’am · 3 steps

Same attacking atom, extra negative charge: the anion always beats its neutral partner as a nucleophile.

  1. Charge rule. When the attacking atom is the same, the negatively charged species is a stronger nucleophile than its neutral form. The extra electron density makes its lone pair much more ready to be donated.
  2. Across a period. When the attacking atoms are different but in the same period, nucleophilicity falls as electronegativity rises. A more electronegative atom holds its lone pairs more tightly, so it shares them less readily.
    OptionPair comparedStronger nucleophileStated order
    (a)F⁻ and OH⁻OH⁻, since O is less electronegative than Fwrong
    (b)H₂O and OH⁻OH⁻, the charged formwrong
    (c)ROH and RO⁻RO⁻, the charged formwrong
    (d)NH₂⁻ and NH₃NH₂⁻, the charged formcorrect
  3. So. The amide ion NH₂⁻ is a stronger nucleophile than ammonia NH₃, so the correct order is (d).

The idea to keep. For the same attacking atom, the anion beats the neutral molecule. For atoms in the same period, the less electronegative atom is the better nucleophile.

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

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Asked about 180 times in JEE Main since 2020. This question is from 2022.