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Choose the Best Answer · Q3

Q.Decreasing order of nucleophilicity is

(a) OH⁻ > NH₂⁻ > ⁻OCH₃ > RNH₂
(b) NH₂⁻ > OH⁻ > ⁻OCH₃ > RNH₂
(c) NH₂⁻ > CH₃O⁻ > OH⁻ > RNH₂
(d) CH₃O⁻ > NH₂⁻ > OH⁻ > RNH₂
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Step 1. Nucleophilicity for these simple, comparably-sized anions/molecules tracks basicity, which in turn tracks how readily each species' conjugate acid gives up a proton -- the weaker the conjugate acid, the stronger the base/nucleophile.

Step 2. NH2−NH_2^- is the conjugate base of ammonia (pKaHpK_{aH} of NH3≈38NH_3 \approx 38) -- an extremely weak acid, making NH2−NH_2^- an exceptionally strong base and the strongest nucleophile of the four.

Step 3. CH3O−CH_3O^- (methoxide) and OH−OH^- (hydroxide) are conjugate bases of methanol and water respectively (pKaH≈15.5pK_{aH} \approx 15.5 and 15.715.7) -- both far weaker bases than NH2−NH_2^-, but methoxide is very slightly the stronger of the two, since the electron-donating (+I+I) methyl group pushes extra electron density onto oxygen, making methoxide a touch more electron-rich (and hence more nucleophilic/basic) than bare hydroxide.

Step 4. RNH2RNH_2 is a neutral amine, not an anion -- neutral species are always markedly weaker nucleophiles than a charged (anionic) species built on the same donor atom, so it ranks last.

Step 5. Putting these together: NH2−>CH3O−>OH−>RNH2NH_2^- > CH_3O^- > OH^- > RNH_2, matching option (c).

✓Final answer

(c) NH₂⁻ > CH₃O⁻ > OH⁻ > RNH₂

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