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The decreasing order of nucleophilicity...

The decreasing order of nucleophilicity for the folllwing anions is
`CH_(3)CO_(2)^(-), CH_(3)O^(-), C_(6)H_(5)O^(-), NO_(3)`

A

`CH_(3)CO_(2)^(-)gt CH_(3)O^(-)gt C_(6)H_(5)O^(-) gt NO_(3)^(-)`

B

`CH_(3)O^(-) gt NO_(3)^(-) gt C_(6)H_(5)O^(-)gt CH_(3)CO_(2)^(-)`

C

`CH_(3)O^(-) gt C_(6)H_(5)O^(-) gt CH_(3)CO_(2)^(-) gt NO_(3)^(-)`

D

`C_(6)H_(5)O^(-) gt CH_(3)O^(-) gt NO_(3)^(-) gt CH_(3)CO_(2)^(-)`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the decreasing order of nucleophilicity for the anions CH₃CO₂⁻, CH₃O⁻, C₆H₅O⁻, and NO₃⁻, we need to analyze the stability of these anions and their ability to donate electrons. Here’s a step-by-step solution: ### Step 1: Understand Nucleophilicity Nucleophilicity refers to the ability of a species to donate electrons. Stronger nucleophiles are less stable because they are more willing to donate their electrons. ### Step 2: Analyze Each Anion 1. **CH₃CO₂⁻ (Acetate Ion)**: - This anion has resonance. The negative charge is delocalized over two oxygen atoms. - While it can donate electrons, the resonance stabilizes the negative charge, making it less nucleophilic compared to anions without resonance. 2. **CH₃O⁻ (Methoxide Ion)**: - This anion does not have resonance. The negative charge is localized on the oxygen atom. - Because there is no resonance to stabilize the negative charge, it is more willing to donate electrons, making it a strong nucleophile. 3. **C₆H₅O⁻ (Phenoxide Ion)**: - This anion also has resonance. The negative charge can be delocalized into the aromatic ring. - The presence of resonance decreases its nucleophilicity compared to CH₃O⁻, but it is still more nucleophilic than CH₃CO₂⁻ because the resonance is less effective than in acetate. 4. **NO₃⁻ (Nitrate Ion)**: - This anion has resonance as well, with the negative charge delocalized over three oxygen atoms. - The negative charge is highly stabilized due to this delocalization, making it the least nucleophilic of the four anions. ### Step 3: Order the Anions Based on Nucleophilicity Based on the analysis: - CH₃O⁻ is the most nucleophilic because it has no resonance stabilization. - C₆H₅O⁻ follows, as it has resonance but is still more reactive than CH₃CO₂⁻. - CH₃CO₂⁻ comes next due to resonance stabilizing the negative charge. - NO₃⁻ is the least nucleophilic due to extensive resonance stabilization. ### Final Order of Nucleophilicity: The decreasing order of nucleophilicity is: **CH₃O⁻ > C₆H₅O⁻ > CH₃CO₂⁻ > NO₃⁻**
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