All Questions
Tagged with carbocation resonance
28
questions
3
votes
1
answer
900
views
Stability of meta ethyl and meta methyl benzene carbocations respectively
It is known that Methyl has a greater +I effect than Ethyl, but here, in this case, the condition is satisfied in the para benzene carbocations whereas, in the meta forms, it is the opposite. Shouldn'...
- 39
1
vote
1
answer
132
views
Carbocation formation and stability from bromo compounds
When heated,the following bromo-species all form carbocations via $\sigma$ bond cleavage. For each structure draw the corresponding carbocation and briefly describe how it is stabilised.
This is my ...
- 29
1
vote
1
answer
136
views
Carbocation stability + determining position of attack on a carbocation in SN1 reaction
It's implied that the right structure is the more stable carbocation because it undergoes the second half of an SN1 reaction, but I'm not entirely sure why:
I'm also not sure why the $\ce{MeOH}$ ...
- 101
-5
votes
1
answer
871
views
Can chlorine show negative mesomeric effect due to presence of d orbital? [closed]
I was wondering in this problem that if chlorine will show positive mesomeric effect as it is at para-position and strength of inductive effect decreases with distance from carbon atom and chlorine ...
0
votes
1
answer
763
views
Among Benzyl carbocation (Ph-CH2+) and Methyl methoxy carbocation (CH3-O-CH2+), why is the latter more stable?
Benzyl Carbocation could form multiple conjugation, then why isn't that stabler? In Methyl methoxy carbocation, Oxygen donates the lone pairs but so does the double bond in the benzyl Carbocation.
- 13
2
votes
1
answer
287
views
Choosing hyperconjugation when resonance doesn't give a reason for stability
Which of the following structures would be least stable?
I initially approached it like this:
As both are allylic carbocations, and that both are in fact resonating structures of the same molecule, ...
- 1,218
0
votes
1
answer
177
views
Why is an Octet Complete Cation more stable than a Resonance Stabilized Cation?
Our instructor taught us about different types of cations: classical, non-classical, resonance stabilized (R.S.C.) and octet complete cation (O.C.C.), and how O.C.C is more stable than a R.S.C.
I did ...
- 13
3
votes
1
answer
643
views
Comparison of carbocation stability in bicyclo compounds
Question
Which is the most stable carbocation ?
Answer
My attempt
I answered as 1 as the first one had +M of -O- and hyperconjugation effect as the positive charge is at para position. Why is the ...
- 357
4
votes
3
answers
419
views
Stability of α-chlorocarbocations
I'm trying to compare the relative stability of two carbocations:
$$\ce{CH3-\overset{+}{C}H-Cl}\quad\text{vs}\quad\ce{CH3-\overset{+}{C}H2}$$
Does the $\ce{Cl}$ exert a +M effect to stabilise the ...
0
votes
3
answers
401
views
Odd looking carbocation stability order [duplicate]
I am studying introductory organic chemistry, suddenly this one started looking odd,
The carbocation stability for three compounds as given by my book is shown below,
Let me call those as ...
user91694
3
votes
1
answer
3k
views
Resonance structures of 4‐aminobut‐3‐en‐2‐ylium
Problem
How many resonance structures can be drawn for the following molecule?
(a) 1
(b) 4
(c) 3
(d) 2
Answer
Question
I think that the molecule can be drawn in three ways, which contradicts the ...
- 179
1
vote
1
answer
378
views
What is the stability order of the carbocation and carboanion?
So I came up with examples as below:
1
2
Now I am confused about the +I and -I effect in these structures since to my knowledge it can only be applied when there is a substituent (I might be wrong)...
- 371
3
votes
2
answers
896
views
Which of the following carbocations is more stable?
Which of the following carbocations is more stable?
I know two major factors in determining carbocation stability: resonance and the number of carbon atoms neighboring the positive carbon. Does the ...
user84854
2
votes
1
answer
908
views
Molecular Orbital Hybridization vs Delocalization for positive charge stabilization
While studying Molecular Orbital Theory, I ran into a comparison of basicity between pyridine and piperidine. The latter was concluded to be more basic because of the sp3 hybridization of the ...
- 757
2
votes
0
answers
40
views
More stable carbocation, tertiary or benzylic? [duplicate]
This is a very confusing question that which is more stable, benzylic or tertiary butyl carbocation?
Some sources say benzylic due to resonance some say tertiary due to +i effect and 9 ...
