What are the major products formed by reaction of methylidene cyclopropane with HBr in CCl4 solvent?

Asked Sep 29 '21 at 08:31

Active Sep 29 '21 at 10:35

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I am confused between two products:

bromomethyl cyclopropane
Allyl bromide

Reason for my confusion: We know CPM cation will be formed which is stabilized by dancing resonating structures why can't bromine attack at one of those dancing structures when positive charge is on end on carbon as shown in figure:

edited Sep 29 '21 at 10:35

Nilay Ghosh

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asked Sep 29 '21 at 08:31

Anurag Singh Tomar

'Dancing resonance' is a somewhat distasteful term to describe the case of cyclopropyl methyl cation. It would sound better (to me, atleast) as sigma-resonance. – TRC Sep 29 '21 at 09:25
Ok thanks for informing. Sir can you please clear my confusion by considering it as sigma resonance – Anurag Singh Tomar Sep 29 '21 at 15:54
"Distasteful" is an interesting way to put it, I'd say it is wrong. Anyway: What is "dancing resonance"? Also related: What is the reason for the exceptional stability of the cyclopropylmethyl carbocation? || To the formalities of the question, please include the actual question in the body, your first sentence makes no sense. Please introduce abbreviations you are using. – Martin - マーチン Sep 29 '21 at 21:32
Also, you first structure appears incorrect to me. The primary cation should be much higher in energy than the tertiary cation. – Martin - マーチン Sep 29 '21 at 21:45
Martin do you mean primary Cyclopropyl methyl carbocation is much much unstable than tertiary Cyclopropyl methyl carbocation? – Anurag Singh Tomar Sep 30 '21 at 02:10
This is not a actual question. This is my doubt sir – Anurag Singh Tomar Sep 30 '21 at 02:13

What are the major products formed by reaction of methylidene cyclopropane with HBr in CCl4 solvent?

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