Linked Questions

0
votes
1answer
86 views

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 ...
0
votes
0answers
17 views

How to compare stabilities of the following carbocations? [duplicate]

I know that hyperconjugation is an important factor in determining carbacation stability but all of them have only 1 alpha hydrogen next factor should be inductive effect i think can anyone tell me ...
9
votes
3answers
2k views

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?
21
votes
1answer
15k views

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 ...
5
votes
2answers
2k views

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? ...
6
votes
2answers
5k views

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". ...
9
votes
1answer
1k views

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 ...
2
votes
2answers
711 views

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 ...
6
votes
1answer
760 views

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 ...
7
votes
1answer
353 views

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 ...
2
votes
1answer
867 views

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 ...
15
votes
2answers
630 views

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 ...
6
votes
0answers
1k views

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 ...
-2
votes
1answer
836 views

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 ...
5
votes
1answer
178 views

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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