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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: Carbocation stability
Forum Index -> Organic Chemistry like the article? email it to a friend.  
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nitigya (260)

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why are people talking about benzylic carbocation when the question asks A benzene ring with one carbon having a positive charge

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coolriya (482)

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im saying only tat.....its benzene ring with a positive charge nd not benzylic cation !

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rida (63)

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ANSER IS B
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nehasomany (2)

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I think its benzen ring which is more stable
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harsha_27 (1343)

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Arre yaar its not benzilic carbocation , it is benzene with a positive charge on one of the six carbons.........it is less stable than vinylic carbon with positive charge........Riya is right......answer is B





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siva7792 (27)

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Benzyl is more stable

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coolriya (482)

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PLS SEE TIS  : Stability of the carbocation increases with the number of alkyl groups bonded to the charge-bearing carbon. Tertiary carbocations are more stable (and form more readily) than secondary carbocations; primary carbocations are highly unstable because, while ionized higher-order carbons are stabilized by Hyperconjugation, unsubstituted (primary) carbons are not. Therefore, reactions such as the SN1 reaction and the E1 elimination reaction normally do not occur if a primary carbocation would be formed. An exception to this occurs when there is a carbon-carbon double bond next to the ionized carbon. Such cations as allyl cation CH2=CH-CH2+ and benzyl cation C6H5-CH2+ are more stable than most other carbocations. Molecules which can form allyl or benzyl carbocations are especially reactive.



the stability of a cation is
influenced by the electronegativity
of the atom bearing the positive charge.
The more electronegative the atom the less stable
the cation
. A vinylic carbocation carries
the positive charge on an sp carbon, which is
more electronegative than an sp2
carbon of an alkyl carbocation.Therefore a primary vinylic  carbocation is less stable than a primary alkyl carbocation.


also : 

Carbocation
Stability
CH3(+) ? RCH=CH(+) < RCH2(+) ? RCH=CR(+) < R2CH(+) ? CH2=CH-CH2(+) < C6H5CH2(+)? R3C(+)
Methyl
1º-Vinyl

2º-Vinyl

1º-Allyl
1º-Benzyl


SOURCE : wikipedia ,
web.chem.ucla.edu/~harding/tutorials/cc.pdf , http://www.cem.msu.edu/~reusch/VirtualText/special1.htm


pls evry 1 giv ur views .............



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x4 (300)

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isnt the benzene ring with one c having a positive charge a benzilic cation ??? unless u remove a h from one of the c u dont get benzene with a c havin +ve charge ???

isnt it resonamce stabilized which is just not another effect cmon it is of the order of 100kj

definitely benzilic carbocation is more stable than vinylic as it has more resonance structures .

POINT OUT THE DIFFERENCE BETWEEN BENZENE WITH ONE C AS +VE CHARGE N BENZILIC CARBOCATION

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RyuAmakusa (461)

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i think BENZENE WITH ONE C AS +VE CHARGE means one of the carbons of the ring has positive
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ramkumar_november (1266)

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for those of you who dont know what is benzylic carbocation , phenylic carbocation,vinylic carbocation here are they : : 





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vsraghuvar (155)

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phenyl carbocation is the most unstable coz order of stability of c-cations is something like-
benzyl>allyl>tertiary>secondary>primary>methyl>vinyl>phenyl...i suppose im right...if im wrong plz supply me with the rite answer



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coolriya (482)

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It is vinyl.....


 


the simple expln is tat it is bcoz..


 


the sp2 carbons has nw changed to sp carbon which hav the character of showing 180 * bond angle...


 


this is possible in vinyl cation nd is not in phenyl due to constrains......


 


 


 


nd also the resonance effest is not predominant  in phenyl as the  positive charge is  makin a vacant p orbital nd it destablises the  resonance effect in the remaining p orbitals.....this is also in case of vinyl where too the p orbitals  make a gud difference.......so with this resonance concept one cant decide the stability in this case...


 


 


 


 


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