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Chloroacetic acid is a stronger acid tha...

Chloroacetic acid is a stronger acid than acetic acid this can be explained using

A

`-M- effect`

B

`-l- effect`

C

`+M-effect`

D

`+l-effect`

Text Solution

AI Generated Solution

The correct Answer is:
To explain why chloroacetic acid is a stronger acid than acetic acid, we can analyze the structural and electronic differences between the two compounds. ### Step-by-Step Solution: 1. **Identify the Structures**: - Chloroacetic acid (ClCH2COOH) consists of a chloro group (Cl) attached to the carbon adjacent to the carboxylic acid group (-COOH). - Acetic acid (CH3COOH) has a methyl group (CH3) attached to the same carbon. 2. **Understand Acid Strength**: - The strength of an acid is determined by the stability of its conjugate base after the acidic hydrogen (H+) is released. - The more stable the conjugate base, the stronger the acid. 3. **Conjugate Bases**: - When acetic acid donates a proton (H+), it forms the acetate ion (CH3COO-). - When chloroacetic acid donates a proton, it forms the chloroacetate ion (ClCH2COO-). 4. **Analyze the Conjugate Bases**: - The acetate ion has a methyl group (CH3), which is an electron-donating group (+I effect). This increases electron density on the conjugate base, making it less stable. - The chloroacetate ion has a chloro group (Cl), which is an electron-withdrawing group (-I effect). This decreases electron density on the conjugate base, stabilizing it. 5. **Effect of Electron-Withdrawing Groups**: - The presence of the chlorine atom in chloroacetic acid pulls electron density away from the carboxylate ion, increasing its stability compared to the acetate ion. - The increased stability of the chloroacetate ion makes chloroacetic acid a stronger acid than acetic acid. 6. **Conclusion**: - Therefore, the reason chloroacetic acid is a stronger acid than acetic acid is due to the -I effect of the chlorine atom, which stabilizes the conjugate base. ### Final Answer: Chloroacetic acid is a stronger acid than acetic acid due to the -I effect of the chlorine atom, which stabilizes the conjugate base. ---
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