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Explain which is a stronger acid. CH(...

Explain which is a stronger acid.
`CH_(3)- overset(O)overset(||)C - CH_(3) " & " CH_(3)- overset(O)overset(||)C - CH_(2)CN `

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To determine which of the two compounds is a stronger acid, we need to analyze their ability to lose a proton (H⁺) and the stability of the resulting carbanion. ### Step 1: Identify the Compounds The two compounds we are comparing are: 1. **Compound A:** CH₃C(=O)CH₃ (Acetone) 2. **Compound B:** CH₃C(=O)CH₂CN (Acetyl cyanide) ### Step 2: Determine the Acidic Hydrogen In both compounds, the acidic hydrogen is the one attached to the carbon adjacent to the carbonyl group (C=O). - For **Compound A**, the acidic hydrogen is from the CH₃ group adjacent to the carbonyl. - For **Compound B**, the acidic hydrogen is from the CH₂ group adjacent to the carbonyl. ### Step 3: Remove the Acidic Hydrogen When we remove the acidic hydrogen (H⁺) from each compound, we form the corresponding carbanions: - **From Compound A:** - CH₃C(=O)CH₃ → CH₃C(=O)C⁻H₂ (carbanion) - **From Compound B:** - CH₃C(=O)CH₂CN → CH₃C(=O)C⁻H + CN (carbanion) ### Step 4: Analyze the Stability of the Carbanions The stability of the carbanion is crucial in determining the strength of the acid. A more stable carbanion indicates a stronger acid. - **For Compound A's Carbanion:** - The carbanion is stabilized by resonance with the carbonyl group. However, both methyl groups (CH₃) do not provide significant stabilization. - **For Compound B's Carbanion:** - The carbanion is also stabilized by resonance with the carbonyl group. Additionally, the presence of the cyano group (CN) is an electron-withdrawing group. This group pulls electron density away from the carbanion, further stabilizing the negative charge. ### Step 5: Compare the Stability - The carbanion from **Compound B** is more stable due to the dual stabilization: 1. Resonance stabilization from the carbonyl group. 2. Electron-withdrawing effect from the cyano group. ### Conclusion Since the carbanion formed from **Compound B (CH₃C(=O)CH₂CN)** is more stable than that from **Compound A (CH₃C(=O)CH₃)**, **Compound B is the stronger acid**. ### Summary - **Stronger Acid:** CH₃C(=O)CH₂CN (Acetyl cyanide) - **Weaker Acid:** CH₃C(=O)CH₃ (Acetone)
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MOTION-GOC-Exercise - 3
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  10. Correct order of basic strength in gas phase is (I) CH(3)-NH(2) (II...

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  11. Write increasing order of basic strength of following: (a)NH(3)" "...

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  12. Write increasing order of basic strength of following: (a)CH(3) - C...

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  13. Write increasing order of basic strength of following: (a)CH(3) -un...

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  14. Arrange the following compound in decreasing order of their basicity. ...

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  15. Arrange the following compound in decreasing order of their basicity. ...

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  16. Consider the following bases: (I) o-nitroaniline (II) m-nitroanili...

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  17. Consider the basicity of the following aromatic amines: (I) aniline ...

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  18. Which one of the following is least basic in character?

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  19. In each of the following pair of compounds, which is more basic in aqu...

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  20. In each of the following pair of compounds, which is more basic in aqu...

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