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Arrange living power of given nucleophil...

Arrange living power of given nucleophilic groups:
`CH_(3)-underset(O)underset(||)overset(O)overset(||)S-overset(ө)O`
(2) `F_(3)C-underset(O)underset(||)overset(O)overset(||)S-overset(ө)O`
(3) `CH_(3)-overset(O)overset(||)C-overset(ө)O`
(4) `F_(3)C-overset(O)overset(||)C-overset(ө)O`

A

2, 1, 4, 3

B

2, 4, 3, 1

C

2, 1, 3, 4

D

2, 4, 3, 1

Text Solution

AI Generated Solution

The correct Answer is:
To arrange the given nucleophilic groups in decreasing order of their nucleophilic strength, we can follow these steps: ### Step 1: Identify the Nucleophilic Sites The nucleophilic sites in all the given compounds are oxygen atoms. This means that the nucleophilic strength will be influenced by the surrounding groups attached to the oxygen. ### Step 2: Determine the Basic Strength The basic strength of a nucleophile is related to its ability to donate a pair of electrons. To assess this, we can look at the conjugate acids formed by adding a proton (H⁺) to each nucleophile. The weaker the conjugate acid, the stronger the corresponding base (nucleophile). ### Step 3: Write the Conjugate Acids For each nucleophile, we will write the corresponding conjugate acid by adding H⁺: 1. **Nucleophile 1**: `CH₃-S(=O)(=O)O` → Conjugate Acid: `CH₃-S(=O)(=O)OH` 2. **Nucleophile 2**: `F₃C-S(=O)(=O)O` → Conjugate Acid: `F₃C-S(=O)(=O)OH` 3. **Nucleophile 3**: `CH₃-C(=O)O` → Conjugate Acid: `CH₃-C(=O)OH` 4. **Nucleophile 4**: `F₃C-C(=O)O` → Conjugate Acid: `F₃C-C(=O)OH` ### Step 4: Compare the Acidity of the Conjugate Acids Now we need to compare the acidity of these conjugate acids: - Sulfonic acids (like those from nucleophiles 1 and 2) are generally more acidic than carboxylic acids (like those from nucleophiles 3 and 4). - Among the sulfonic acids, the presence of the `CF₃` group (which has a strong -I effect) will make the conjugate acid more acidic compared to the `CH₃` group (which has a +I effect). ### Step 5: Order of Acidity Based on the above points, we can arrange the acidity of the conjugate acids: 1. `F₃C-S(=O)(=O)OH` (most acidic) 2. `CH₃-S(=O)(=O)OH` 3. `F₃C-C(=O)OH` 4. `CH₃-C(=O)OH` (least acidic) ### Step 6: Determine the Order of Nucleophilic Strength Since the basic strength (and thus nucleophilic strength) is inversely related to the acidity of the conjugate acids, we can arrange the nucleophiles in decreasing order of nucleophilic strength: 1. `F₃C-S(=O)(=O)O` (strongest nucleophile) 2. `CH₃-S(=O)(=O)O` 3. `F₃C-C(=O)O` 4. `CH₃-C(=O)O` (weakest nucleophile) ### Final Answer The order of nucleophilic strength from strongest to weakest is: 1. `F₃C-S(=O)(=O)O` 2. `CH₃-S(=O)(=O)O` 3. `F₃C-C(=O)O` 4. `CH₃-C(=O)O`
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