Benzyl Free Radical:

  • More Resonating structure more will be the stability of the free Radical.

(4 Resonating Structure)
 (7 Resonating structure)
(Tribenzylic free Radical)
(7 Resonating structure)
Stability Order:
Ex.1 Compare the stability of the following free Radical.

Sol. (a) CH3-C0H2 will be most stable due to hyper conjugation
Between 

⇒More s-character
⇒More electronegative
⇒E-density maximum
⇒More repulsion
⇒Less stable

Ans. a > b > c (More repulsion, less stability)

Ex.2 Compare the stability of the following free Radicals

(Therefore this resonating structure is not possible)
Ans. b > a > c

Ex.3

(a) 
(b) 
(c) 
(d) 
Compare the bond energy of the above compounds.

Sol. After forming free radical from the compound

 

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