sign up I login
 advanced
refer a friend - earn nickels!!

Ask & Discuss Questions with Community & Experts

Moderation Team
 90 chars left    advanced
Ask iit jee aieee pet cbse icse state board community Community Discussion Question: answer please !
Forum Index -> Organic Chemistry like the article? email it to a friend.  
Author Message
cutepooja (441)

Blazing goIITian

Olaaa!! Perrrfect answer. 73  [111 rates]

cutepooja's Avatar

total posts: 596    
offline Offline

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


" 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
    
vaibhavbright (160)

Cool goIITian

Olaaa!! Perrrfect answer. 30  [35 rates]

vaibhavbright's Avatar

total posts: 68    
offline Offline

benzyllic > allylic > 3 > 2 > 1


VAIBHAV BEST
< THE GAME IS ON >
 this reply: 2 points  (with Olaaa!! Perrrfect answer.   in 1 votes )   [?]
 
You have to be logged on to rate
  
vaibhavbright (160)

Cool goIITian

Olaaa!! Perrrfect answer. 30  [35 rates]

vaibhavbright's Avatar

total posts: 68    
offline Offline

ofcourse      singlet carbene is more stable dan triplet carbene


as   triplet carbene has 2 unpaired electrons  & is thus more reactive & more unstable


VAIBHAV BEST
< THE GAME IS ON >
 this reply: 0 points  (with Olaaa!! Perrrfect answer.   in 0 votes )   [?]
 
You have to be logged on to rate
  
vaibhavbright (160)

Cool goIITian

Olaaa!! Perrrfect answer. 30  [35 rates]

vaibhavbright's Avatar

total posts: 68    
offline Offline

ofcourse      singlet carbene is more stable dan triplet carbene


as   triplet carbene has 2 unpaired electrons  & is thus more reactive & more unstable


VAIBHAV BEST
< THE GAME IS ON >
 this reply: 0 points  (with Olaaa!! Perrrfect answer.   in 0 votes )   [?]
 
You have to be logged on to rate
  
svj29 (2140)

Blazing goIITian

Olaaa!! Perrrfect answer. 374  [509 rates]

svj29's Avatar

total posts: 776    
offline Offline

@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.


PROGRESS ISN'T MADE BY EARLY RISERS OR HARD WORKERS, BUT BY LAZY PEOPLE TRYING TO FIND EASIER WAY TO DO THE SAME.....SO BE LAZZZZYY!!!!
 this reply: 5 points  (with Olaaa!! Perrrfect answer.   in 1 votes )   [?]
 
You have to be logged on to rate
  
jain108 (437)

Blazing goIITian

Olaaa!! Perrrfect answer. 69  [115 rates]

jain108's Avatar

total posts: 826    
offline Offline

singlet dichlorocarbene is more stable than triplet dichlorocarbene


 


but


 


singlet methylene carbene is less stable than triplet methylene carbene


 


 


(konsa  pooch rai hai)??????)

 this reply: 7 points  (with Olaaa!! Perrrfect answer.   in 2 votes )   [?]
 
You have to be logged on to rate
  
jain108 (437)

Blazing goIITian

Olaaa!! Perrrfect answer. 69  [115 rates]

jain108's Avatar

total posts: 826    
offline Offline

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


 



 


 


 

 this reply: 17 points  (with Olaaa!! Perrrfect answer.   in 4 votes )   [?]
 
You have to be logged on to rate
  
studen9t_iit (114)

Hot goIITian

Olaaa!! Perrrfect answer. 18  [30 rates]

studen9t_iit's Avatar

total posts: 129    
offline Offline

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.


http://www.youtube.com/watch?v=0JurgT5GEnc
 this reply: 0 points  (with Olaaa!! Perrrfect answer.   in 0 votes )   [?]
 
You have to be logged on to rate
  
silverdoe (21)

Cool goIITian

Olaaa!! Perrrfect answer. 3  [6 rates]

silverdoe's Avatar

total posts: 65    
offline Offline
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.

If the path is beautiful, let us not ask where it leads. But if the DESTINATION is beautiful, let us not ask HOW THE PATH IS.
 this reply: 2 points  (with Olaaa!! Perrrfect answer.   in 1 votes )   [?]
 
You have to be logged on to rate
  
cutepooja (441)

Blazing goIITian

Olaaa!! Perrrfect answer. 73  [111 rates]

cutepooja's Avatar

total posts: 596    
offline Offline

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


" 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
 this reply: 0 points  (with Olaaa!! Perrrfect answer.   in 0 votes )   [?]
 
You have to be logged on to rate
  
x4 (302)

Scorching goIITian

Olaaa!! Perrrfect answer. 52  [73 rates]

x4's Avatar

total posts: 293    
offline Offline
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 .

COPYRIGHT :
The copyright for the facts written above is held by x4
no part of the facts may be reproduced , stored in ur memory , or transmitted by any means without pror written permission from x4
****VIOLATERS ARE LIABLE FOR PROSECUTION UNDER THE " X4 GOIIT ACT 2008 ".****
 this reply: 0 points  (with Olaaa!! Perrrfect answer.   in 0 votes )   [?]
 
You have to be logged on to rate
  
PATELTEJAS (2)

Cool goIITian

Olaaa!! Perrrfect answer. 0  [1 rates]

PATELTEJAS's Avatar

total posts: 34    
offline Offline

in benzylic carbocation due to resonance the positive charge will gel delocalized so its over all stability will increase

 this reply: 0 points  (with Olaaa!! Perrrfect answer.   in 0 votes )   [?]
 
You have to be logged on to rate
  
svj29 (2140)

Blazing goIITian

Olaaa!! Perrrfect answer. 374  [509 rates]

svj29's Avatar

total posts: 776    
offline Offline
@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...

PROGRESS ISN'T MADE BY EARLY RISERS OR HARD WORKERS, BUT BY LAZY PEOPLE TRYING TO FIND EASIER WAY TO DO THE SAME.....SO BE LAZZZZYY!!!!
 this reply: 0 points  (with Olaaa!! Perrrfect answer.   in 0 votes )   [?]
 
You have to be logged on to rate
  
svj29 (2140)

Blazing goIITian

Olaaa!! Perrrfect answer. 374  [509 rates]

svj29's Avatar

total posts: 776    
offline Offline

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