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Consider the following compounds O(2)...

Consider the following compounds
`O_(2)N-CH_(2)-underset((I))overset(O)overset(||)C-OH" "F-CH_(2)-underset((II))overset(O)overset(||)C-OH" "Ph-CH_(2)-underset((III))overset(O)overset(||)C-OH" "CH_(3)-underset((IV))(CH_(2))-overset(O)overset(||)C-OH`
Which statement is/are correct :

A

`I gt II gt III gt IV` (Acidic strength order)

B

I is most acidic because of -M effect of `-NO_(2)` group

C

I is most acidic because of -I effect of `-NO_(2)` group

D

IV is least acidic because of `+I` Effect.

Text Solution

AI Generated Solution

The correct Answer is:
To determine the correct statements regarding the acidic strength of the given compounds, let's analyze each compound step by step. ### Step 1: Identify the compounds The compounds given are: 1. **Compound I:** O₂N-CH₂-C(=O)-OH (Nitro group) 2. **Compound II:** F-CH₂-C(=O)-OH (Fluoro group) 3. **Compound III:** Ph-CH₂-C(=O)-OH (Phenyl group) 4. **Compound IV:** CH₃-CH₂-C(=O)-OH (Methyl group) ### Step 2: Analyze the effects of substituents - **Compound I (NO₂):** The nitro group (NO₂) is a strong electron-withdrawing group due to its -I (inductive) and -M (mesomeric) effects. This stabilizes the negative charge on the oxygen atom after the release of H⁺, making it highly acidic. - **Compound II (F):** The fluorine atom (F) also exhibits a -I effect, which stabilizes the negative charge, but it is less effective than the nitro group. Therefore, it is less acidic than Compound I. - **Compound III (Ph):** The phenyl group (Ph) has a -I effect but is less effective than both NO₂ and F. Thus, it is less acidic than Compound II. - **Compound IV (CH₃):** The methyl group (CH₃) has a +I effect, which destabilizes the negative charge on the oxygen after H⁺ release, making it the least acidic among the four compounds. ### Step 3: Establish the order of acidity Based on the analysis: - Compound I (NO₂) is the most acidic. - Compound II (F) is next. - Compound III (Ph) follows. - Compound IV (CH₃) is the least acidic. The order of acidity is: **I > II > III > IV** ### Step 4: Evaluate the statements 1. **Statement 1:** "1 > 2 > 3 > 4" - **Correct** (as derived from the analysis). 2. **Statement 2:** "The first structure is most acidic because of the -M effect of NO₂ group" - **Correct** (NO₂ has both -I and -M effects contributing to acidity). 3. **Statement 3:** "The third structure is most acidic because of the -I effect of NO₂ group" - **Incorrect** (the third structure is not the most acidic; it is the first structure). 4. **Statement 4:** "IV is least acidic because of +I effect" - **Correct** (the +I effect of CH₃ destabilizes the negative charge). ### Conclusion The correct statements are: - Statement 1 - Statement 2 - Statement 4
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