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Which of the following is the correct or...

Which of the following is the correct order of stability of free radicals ?

A

benzyl `gt` allyl `gt 2^(underset(-)o) gt 1^(underset(-)o)`

B

allyl `gt` benzyl `gt 2^(underset(-)o) gt 1^(underset(-)o)`

C

allyl `gt 2^(underset(-)o) gt 1^(underset(-)o)` benzyl

D

benzyl `gt 2^(underset(-)o) gt 1^(underset(-)o)` allyl

Text Solution

AI Generated Solution

The correct Answer is:
To determine the correct order of stability of free radicals, we need to analyze the stability of the following radicals: benzyl, allyl, secondary, and primary. ### Step-by-Step Solution: 1. **Identify the Structure of Each Radical:** - **Benzyl Radical:** This can be represented as \( \text{C}_6\text{H}_5\text{CH}_2^{\cdot} \) (where the radical is on the \( \text{CH}_2 \) group attached to a benzene ring). - **Allyl Radical:** This can be represented as \( \text{CH}_2=CH-\text{CH}_2^{\cdot} \) (where the radical is on the terminal \( \text{CH}_2 \) group). - **Secondary Radical:** This can be represented as \( \text{CH}_3-\text{CH}^{\cdot}-\text{CH}_3 \) (where the radical is on a carbon attached to two other carbons). - **Primary Radical:** This can be represented as \( \text{CH}_3-\text{CH}_2^{\cdot} \) (where the radical is on a carbon attached to only one other carbon). 2. **Analyze the Stability Factors:** - **Benzyl Radical:** The benzyl radical is highly stabilized by resonance. The radical can delocalize over the aromatic system, making it very stable. - **Allyl Radical:** The allyl radical is also stabilized by resonance, but to a lesser extent than the benzyl radical. The radical can delocalize between the two terminal carbons. - **Secondary Radical:** The secondary radical is stabilized by hyperconjugation and inductive effects from the adjacent carbon atoms, but it does not have resonance stabilization. - **Primary Radical:** The primary radical is the least stable as it has no resonance stabilization and minimal hyperconjugation. 3. **Rank the Stability:** - Based on the above analysis, we can rank the stability of the radicals: - **Most Stable:** Benzyl Radical (due to resonance) - **Next Stable:** Allyl Radical (due to resonance) - **Next Stable:** Secondary Radical (due to hyperconjugation) - **Least Stable:** Primary Radical (no resonance and minimal hyperconjugation) 4. **Final Order of Stability:** - The correct order of stability is: \[ \text{Benzyl} > \text{Allyl} > \text{Secondary} > \text{Primary} \] 5. **Check the Options:** - The correct option matches the derived order: Benzyl > Allyl > Secondary > Primary. ### Conclusion: The correct order of stability of free radicals is **Benzyl > Allyl > Secondary > Primary**.
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