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In which of the following pairs A is mor...

In which of the following pairs A is more stable than B?

A

B

C

D

`{:(A,B),(Ph_(3)C^(.),(CH_3)_(3)C^(.)):}`

Text Solution

AI Generated Solution

The correct Answer is:
To determine which of the following pairs has A being more stable than B, we will analyze each option based on the stability of free radicals and the effects of hybridization, resonance, and steric factors. ### Step-by-Step Solution: 1. **Analyze Option A: Cyclohexane vs. Methyl-substituted Cyclohexane** - **A**: Cyclohexane (C6H12) - **B**: Methyl-substituted Cyclohexane (C6H11-CH3) - In this case, we are comparing a secondary free radical (methyl-substituted) with a tertiary free radical (if we assume the methyl group is on a carbon that makes it tertiary). - Tertiary radicals are more stable than secondary radicals due to hyperconjugation and inductive effects. - **Conclusion**: B is more stable than A. 2. **Analyze Option B: Three-membered Ring vs. Six-membered Ring** - **A**: Three-membered ring (less stable due to angle strain) - **B**: Six-membered ring (more stable due to less strain) - Six-membered rings are generally more stable than three-membered rings due to less angle strain and torsional strain. - **Conclusion**: B is more stable than A. 3. **Analyze Option C: Cyclohexane Radical vs. SP2 Hybridized Radical** - **A**: Cyclohexane radical (sp3 hybridized) - **B**: SP2 hybridized radical - SP2 hybridized radicals are less stable than sp3 hybridized radicals due to the increased s-character in sp2 (33% vs. 25% in sp3), leading to higher energy and less stability. - **Conclusion**: B is more stable than A. 4. **Analyze Option D: Phenyl Radical vs. Tertiary Carbon Radical** - **A**: Phenyl radical (C6H5-CH) - **B**: Tertiary carbon radical (C(CH3)3) - The phenyl radical is stabilized by resonance from the three benzene rings, which provides significant stabilization. - The tertiary carbon radical is stabilized by hyperconjugation but lacks the resonance stabilization that the phenyl radical has. - **Conclusion**: A is more stable than B due to resonance stabilization. ### Final Conclusion: The only pair where A is more stable than B is in option D.
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