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Which of the following is second ion is ...

Which of the following is second ion is more stable than the first

A

`underset("I")(CH_(2)=Coverset(Theta)H) and underset("II")(CH=overset(theta)C)`

B

`underset("I")(C_(6)H_(5)-Coverset(Theta)H_(2)) and underset("II")(CH_(2)=CH-Coverset(Theta)H_(2))`

C

`CH_(3)-Coverset(Theta)H-CH=CH_(2) and Coverset(Theta)H_(2)-CH=CH_(2)`

D

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AI Generated Solution

The correct Answer is:
To determine which of the following second ions is more stable than the first, we will analyze the stability of carbanions formed from different compounds. ### Step-by-Step Solution: 1. **Identify the Compounds**: - We have four options (A, B, C, D) with different structures. We need to analyze the stability of the carbanions formed from these compounds. 2. **Analyze Option A**: - The first compound is a vinylic carbonyl (CH2=CH-) and the second is an acetylenic carbonyl (CH≡C-). - The acetylenic carbon has an sp-hybridized carbon, which has 50% s-character, making it more acidic and thus forming a more stable carbanion (CH≡C-). - The vinylic carbon has an sp²-hybridized carbon with 33.33% s-character, making it less stable. - **Conclusion**: The second ion (CH≡C-) is more stable than the first (CH2=CH-). 3. **Analyze Option B**: - The first species is a benzylic carbanion (C6H5-CH2-) which can resonate through the benzene ring, forming four resonating structures. - The second species is CH2=CH-CH2-, which has only two resonating structures. - More resonating structures indicate greater stability. - **Conclusion**: The first ion (C6H5-CH2-) is more stable than the second (CH2=CH-CH2-). 4. **Analyze Option C**: - The first species is CH3-CH- (with a negative charge) and the second species is CH2=CH-CH2-. - The CH3 group has a +I effect, which destabilizes the carbanion by increasing electron density. - The second species does not have this destabilizing effect. - **Conclusion**: The second ion (CH2=CH-CH2-) is more stable than the first (CH3-CH-). 5. **Analyze Option D**: - The first compound has a double bond and a negative charge, making it aromatic (follows Huckel's rule with 6 π electrons). - The second compound is aliphatic and does not have aromaticity. - Aromatic compounds are generally more stable than aliphatic compounds. - **Conclusion**: The first ion is more stable than the second. ### Final Conclusion: The only option where the second ion is more stable than the first is **Option A** and **Option C**.
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