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Ask iit jee aieee pet cbse icse state board experts Expert Question: free radial stability
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kislay (1108)

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pls solve


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kislay (1108)

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i want to ask how stability of 5 and 3 has been compared?????

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rooney (894)

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5 has more resonance structures than 3. so its more stable.

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kislay (1108)

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HOW CAN U SHOW RESONANCE IN 5??

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Hmmm...I dont get how V is least stable when it has max reso structures and the lone pair is getting delocalised maximum.

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madman (239)

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no rooney
there is no lone pair delocalization in either of them.
look carefully the carbon is a free radical

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10904him (98)

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See in the other structures carbene may form in trying out resonance hence they are most unstable.Further onehaving three pi bonds in ring forces carbene formation more than the single bond ring.Hence the result................
 
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mukulss (493)

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in 5
aromaticity of benzene ring has damaged bcoz it now does not follw
(4n+2)pie syatem
so it is the least stable
others can be judged in different ways
hope u can make it now

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rooney (894)

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Been long since I did organic. Anyways, isnt this what happens ?



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kislay (1108)

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@mukuluss, aromaticity gives extra stability to compounds than other comparable non aromatic compounds,and absence of it doesn'dt redues the stablity(than the nortmal value),isnt it????????


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kislay (1108)

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@rooney
two consecutive double bond in any ring system is not possible, due to very high angle strain , so resonance shown by u are not possible.....

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madhusudan.chavan (826)

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Stability of free radical depends on i) Hyperconjugation and ii) resonance effect.
In case of IV & II resonance effect can expalin the stability.
In case of phenyl free radical no other structure would be possible hence is least stable.For structure III, one structure may be possible by using hydrogen atom on adjacent carbon( benzyne type triple bond). Hence III should be more stable than V. However, the same anology does not work for vinyl free radical, it is less stable than phenyl free radical.
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kislay (1108)

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if triple bond resonance is possibnle in III tehn why it is not possible in V
???????

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santosh05 (279)

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v is aromatic     so it has to b most stable.......ans gvn is wrong
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