Question:
The correct order of the rate of the reaction for the following reaction with respect to nucleophiles is :
\( CH_3Br + Nu^\ominus \rightarrow CH_3Nu + Br^\ominus \)
The correct order of the rate of the reaction for the following reaction with respect to nucleophiles is :
\( CH_3Br + Nu^\ominus \rightarrow CH_3Nu + Br^\ominus \)
\( CH_3Br + Nu^\ominus \rightarrow CH_3Nu + Br^\ominus \)
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Stronger base = Better nucleophile (when the attacking atom is the same). Hydroxide is always a very strong nucleophile compared to carboxylates or resonance-stabilized phenoxides.
Updated On: Feb 4, 2026
- \( CH_3COO^\ominus>PhO^\ominus>^\ominus OH>ClO_4^\ominus \)
- \( ClO_4^\ominus>CH_3COO^\ominus>^\ominus OH>PhO^\ominus \)
- \( ^\ominus OH>PhO^\ominus>CH_3COO^\ominus>ClO_4^\ominus \)
- \( PhO^\ominus>^\ominus OH>CH_3COO^\ominus>ClO_4^\ominus \)
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The Correct Option is C
Solution and Explanation
Step 1: Understanding the Concept:
The reaction is an \( S_N2 \) substitution on a methyl halide. The rate is directly proportional to the nucleophilicity of the attacking species. For nucleophiles attacking via the same atom (oxygen), nucleophilicity follows the same trend as basicity.
Step 3: Detailed Explanation:
Basicity and nucleophilicity increase as the ability to donate an electron pair increases. This is inversely related to the stability of the anion.
Stability of anions depends on resonance and the acidity of conjugate acids :
1. \( ClO_4^\ominus \): Conjugate acid is \( HClO_4 \), a superacid. The anion is extremely stable due to four oxygen resonance structures. It is a very poor nucleophile.
2. \( CH_3COO^\ominus \): Conjugate acid is acetic acid (\( pKa \approx 4.8 \)). Moderate stability.
3. \( PhO^\ominus \): Conjugate acid is phenol (\( pKa \approx 10 \)). Stability is provided by benzene ring resonance.
4. \( ^\ominus OH \): Conjugate acid is water (\( pKa \approx 14 \)). It is the strongest base among the group and hence the best nucleophile.
The basicity and nucleophilicity order is : \( ^\ominus OH>PhO^\ominus>CH_3COO^\ominus>ClO_4^\ominus \).
Step 4: Final Answer:
The correct rate order is given by Option (C).
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