All Questions
Tagged with carbocation aromatic-compounds
17
questions
1
vote
1
answer
281
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Can a carbocation ever be more stable than a neutral molecule?
The question is about finding the most stable molecule or species. Now my thought process was that cyclopropenylidene(1) was a carbene so would be unstable even though it is aromatic. Cyclopenta-1,3-...
- 97
8
votes
1
answer
740
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Is tropylium cyclopentadienide possible?
Has this ever been tried? The respective aromatic ions are readily accessible, e. g., in the form of sodium cyclopentadienide and tropylium bromide. It shouldn't be hard to just combine these two ...
- 81
-3
votes
2
answers
639
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What is the hybridization of the carbon atom in cyclopropenyl carbocation?
The hybridization of the carbocation in the cyclopropenyl carbocation (which is aromatic) should be sp as it as the + and also is in a ring. But the carbocation has a sp2 hybridization, why?
For ...
- 37
3
votes
1
answer
900
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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
-5
votes
1
answer
871
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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 ...
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
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
0
answers
40
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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 ...
4
votes
0
answers
507
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Friedel–Crafts alkylation of benzene with propyl chloride [duplicate]
This is a question from my textbook:
Why does the alkylation of benzene with 1-chloropropane give (propan-2-yl)benzene and not (propan-1-yl)benzene?
The book shows the reaction with chloromethane ...
- 469
10
votes
1
answer
1k
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Product of Friedel-Crafts cyclisation of (3-methylpent-4-en-1-yl)benzene
My proposed mechanism and final product is:
But the book says the answer is:
I know that a 6 membered ring is more stable than a 5 membered ring so I made the product with the 6 membered ring (...
- 2,381
10
votes
1
answer
4k
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Relative stabilities of tropylium and cyclopropenyl carbocations
How can the stabilities of the tropylium and cyclopropenyl carbocations be compared?
Both are aromatic according to Hückel's rule. I think that to compare the stabilities, we must either count the ...
- 515
1
vote
0
answers
332
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Is the Friedel-Crafts alkylation of benzene with cyclopropenyl chloride feasible?
Is the Friedel-Crafts alkylation of benzene with cyclopropenyl chloride according to the following scheme feasible?
Would the attack of the benzene towards the cycopropylium take place?
I am ...
- 2,381
10
votes
1
answer
10k
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Why is cyclopentadiene more stable than its aromatic counterpart cyclopentadienyl anion?
What will be the order of stability?
The answer key says that the stability order is: cyclopentadiene > cyclopentadienyl anion > cyclopentadiene cation
According the me it should be: ...
- 2,381
2
votes
1
answer
4k
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Formation of Tropylium carbocation
I've read that Tropylium carbocation is formed by the ring expansion of benzyl carbocation. But in benzyl carbocation, the $\ce{C}$ atoms in the benzene ring are $sp^2$ hybridized i.e. $120^\circ$ is ...
- 401
35
votes
1
answer
4k
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Unusual Friedel–Crafts alkylation with pivaloyl chloride
In class we were told of an anomalous Friedel–Crafts reaction with a tertiary acid chloride — $\ce{(CH3)3CCOCl}$, or pivaloyl chloride. When this reacts with benzene in the presence of $\ce{AlCl3}$, ...
- 2,725