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![[Post New]](/templates/default/images/icon_minipost_new.gif) 21 Jun 2008 17:36:45 IST
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pls explain me this first of all i read arihant organic chemistry there i found something which i need to clarify
pls explain me stability order of carbocation
benzylic~3'>allylic~2'>1'>ch3+
i thought that non resonating are less stable than resonating
ques 2
singlet carbene is more stable than triplet carbene? how
there are more question i will edit it so please keep looking them !
thanks
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" I've shed many tears. But after, I realize, why am I crying? No matter how bad it got, it could be worse. No matter how much you think it's not going to be ok, eventually it will be. You just have to let it be."
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![[Post New]](/templates/default/images/icon_minipost_new.gif) 21 Jun 2008 17:40:15 IST
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benzyllic > allylic > 3 > 2 > 1
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VAIBHAV BEST
< THE GAME IS ON > |
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![[Post New]](/templates/default/images/icon_minipost_new.gif) 21 Jun 2008 17:45:18 IST
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ofcourse singlet carbene is more stable dan triplet carbene
as triplet carbene has 2 unpaired electrons & is thus more reactive & more unstable
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VAIBHAV BEST
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![[Post New]](/templates/default/images/icon_minipost_new.gif) 21 Jun 2008 17:47:15 IST
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ofcourse singlet carbene is more stable dan triplet carbene
as triplet carbene has 2 unpaired electrons & is thus more reactive & more unstable
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VAIBHAV BEST
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![[Post New]](/templates/default/images/icon_minipost_new.gif) 21 Jun 2008 17:53:30 IST
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@TC
there are many mistakes in arihant, this is one of em.
@vaibhavbright
Triplet carbene is much more stable than singlet carbene.
i'm damn sure bout it, if ya have any probs, go 4 any good book.
the reason is that singlet carbene has unshared electrons in the same orbital, therefore, more repulsions will be there, and henceforth less stabitliy.
and one more reason triplet carbene will have more electron transfers (internal) to enhance itz stabitliy.
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![[Post New]](/templates/default/images/icon_minipost_new.gif) 21 Jun 2008 17:55:04 IST
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singlet dichlorocarbene is more stable than triplet dichlorocarbene
but
singlet methylene carbene is less stable than triplet methylene carbene
(konsa pooch rai hai)??????)
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![[Post New]](/templates/default/images/icon_minipost_new.gif) 21 Jun 2008 18:32:58 IST
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there r 2 diff types of carbene which depends upon whether the two unpaired electrons are placed in one orbital (singlet) or in two orbitals(triplet)
the stability is decided by interlectronic repulsion..
in a triplet carbene electrons are in diff orbitals so repulsion is min. but in singlt energy is required to over power the repulsion so singlet is less stable
but this happens only in case of methylene carbene
now taking dichloro carbene dueto intereectronic repulsion betwen chlorine lp electrons
the 2 elec . of carbne .........the two ele r easily paired up in one obital
now singlet carbene is more stable(hav less energy) than triplet

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![[Post New]](/templates/default/images/icon_minipost_new.gif) 21 Jun 2008 18:36:54 IST
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About the carbocation stability,
3 degree will be more stable because alkyl groups have a +I effect which implies that they release electrons to the adjoining atom if it is deficient.Since more electrons will be provided by 3 alkyl groups than by two and so on,therefore 3 degree carbocation is more stable than 2 degree and so on.
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3> benzylic~allylic>2>1>vinyl>methyl.
The order changed in 2005 after they had new developments.
And singlet carbene is called 'hot carbene' ;-) because its more reactive than triplet.
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![[Post New]](/templates/default/images/icon_minipost_new.gif) 21 Jun 2008 20:54:43 IST
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wat? silverdo pls give an explaination for it i too agree with svj29 abt the mistake thing !
and studen9t_iit i wanna ask u dat how come a structure getting stabilised by resonance be less stable than non resonanting strucutre
pls solve my querie and thanks for the reply yet thnks
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" I've shed many tears. But after, I realize, why am I crying? No matter how bad it got, it could be worse. No matter how much you think it's not going to be ok, eventually it will be. You just have to let it be."
EXPECT MORE FROM URSELF THAN FRM OTHERS AS EXPECTATION FRM OTHERS HURTS U WHILE FROM UR SELF INSPIRES U A lot |
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![[Post New]](/templates/default/images/icon_minipost_new.gif) 21 Jun 2008 21:38:18 IST
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ya i had the same doubt earlier but see
firstly , 3 degree carbocat has 9 alpha hydrogens involved in hyperconjugation so compared to allylic where there are 2 resionating structures it is more stable . so i guess first part is clear .
and about stability of singlet and triplet carbene whenever effects like resonance , backbonding ,hyp. are absent triplet is more stable , and vice versa . svj is right in his explaination but mine can be generally applied .
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![[Post New]](/templates/default/images/icon_minipost_new.gif) 21 Jun 2008 22:05:41 IST
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in benzylic carbocation due to resonance the positive charge will gel delocalized so its over all stability will increase
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![[Post New]](/templates/default/images/icon_minipost_new.gif) 22 Jun 2008 12:04:21 IST
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@jain108 if we refer to singlet carbene or triplet carbene then we simply mean that we are talking of methylene carbene... untill and unless given in the question we can't take examples of carbenes from our mind...so the answer can only be triplet carbene...untill and unless specified...
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![[Post New]](/templates/default/images/icon_minipost_new.gif) 22 Jun 2008 12:23:40 IST
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WelL this is the most precise answer,
(i'm damn sure about mah answer)
3degree > benzylic > allylic > 2degree >1degree
Explanation:
though the stability of benzylic carbocation and 3degree
carbocation are almost same, but for single choice questions the
answer preferred would be 3 degree.
Reason for this unusual happening...
if we see the deficiency in carbocation is much more a free radical,
so due to more deficiency hyperconjugation effect will happen at a
very fast rate, hence increasing the stability given by
hyperconjugation. Hyperconjugation is much more prominent and
dominating in case of carbocations in comparison to free radicals.
Though its not that dominating as much as resonance is...
but now if we compare benzylic and 3degree, we find that there
are 9 hyperconjugating structures in 3deg and 3 resonating
structures in benzylic. Comparing the ratio of canonical forms, we
clearly see that the stability given by 9 hyperconjugating structures
is some what equivalent to the stability given by the 3 canonical
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