Linked Questions
23 questions linked to/from What is the reason for the exceptional stability of the cyclopropylmethyl carbocation?
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Stability of tertiary carbocation [duplicate]
Our teacher told us that a carbocation connected to 3 cyclopropane rings is among the most stable carbocations. But I am unable to understand how, as resonance (the most important factor governing ...
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3
answers
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Can a organic compounds such as hydrocarbons contain an ionic bond?
Can organic compounds like hydrocarbons have types of bonds other than covalent bonds? Can they also possess ionic bonds?
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Stability Comparison between the Tropylium and Tricyclopropylcarbinyl Carbocation
Why is the Tropylium carbocation less stable than the tricyclopropylcarbinyl carbocation? The tricyclopropylcarbinyl carbocation undergoes a sigma-tropic rearrangement whereas tropylium is highly ...
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2
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Carbocation rearrangement involving three membered rings
Question:
Taking into account of various carbocations and, as well as the rules governing mechanisms of carbocation rearrangements, which reaction is most likely to occur during the given reaction?
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What is "dancing resonance"?
While searching the Internet for information about the tricyclopropylmethyl carbocation, I found a site (askiitians.com) where it said that its stability was due to "dancing (superfast) resonance".
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1
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What is the reason for the exceptional stability of tricyclopropyl-cyclopropenyl carbocation?
The stability order of the following is:
A. III > II > I > IV
B. II > III > I > IV
C. I > III > IV > II
D. I > III > II > IV
Answer:
I came across a question ...
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3
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Why are two three-membered rings preferred to a single five-membered ring in the reaction of a dihalide with alcoholic KOH?
The given answer is 1,1-dicyclopropylmethanone:
Step 1 is abstraction of acidic H by the strong base. Then, there's surely going to be anchimeric assistance. But there can be two places where the ...
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2
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2
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Can an organic compound undergo ring contraction to give more stable carbocation? [duplicate]
Throughout my journey in organic chemistry I’ve only seen ring expansions by a compound in order to attain more stability, but yesterday I thought about the following reaction.
I feel that ring ...
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2
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1
answer
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Why doesn't cyclopropyl methyl carbocation stabilises itself by ring expansion? [duplicate]
I have been taught that ring expansion stabilises smaller cyclic compounds to a great extent. So why does cyclopropyl methyl carbocation shows such type of resonance
rather than expanding its ring
...
user66707
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1
answer
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Semipinacol-type rearrangement leading to ring expansion
What will be the major product in the following reaction?
I tried to work out the mechanism, which starts with protonation of the alkene, and I got C to be the answer (which is the answer in the book ...
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9
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1
answer
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Why does this ring contraction take place in the following nucleophilic substitution? [closed]
While attempting this problem I thought that P1 would simply be Bromine getting substituted by OH through nucleophilic substitution.
P2 would give a product formed through ring expansion as a 4 ...
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6
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1
answer
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Mechanism for the conversion of an unsaturated alkyl halide to an alcohol
Question:
Predict the mechanism for the following reaction:
Attempt:
I thought it will proceed through SN1 mechanism as $\ce{H_2O}$ is involved (solvolysis). So I proceeded with the formation of a ...
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7
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1
answer
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Hydrolysis of (chloromethyl)cyclopropane: Is but-3-en-1-ol a possible product?
This is from one of the practice papers for the JEE , asks for possible hydrolysis products of (chloromethyl)cyclopropane .
Product A happens to be due to stability of cyclopropyl methyl carbocation.
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1
answer
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Stability order of carbocations [duplicate]
These are some of the most stable carbocations, but what is the relative stability order between them.
According to me it should be: C>D>B>A........ I came to this conclusion because both C and D ...
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SN1 reactivity order for chloromethyl methyl ether and trityl chloride
Compare the reactivity order towards SN1 reaction for:
(2-chloropropan-2-yl)cyclopropane
$\ce{CH3OCH2Cl}$
$\ce{Ph3CCl}$
Owing to the exceptional stability of cyclopropyl ethyl ...
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