2k views

Which of the following is the more stable carbocation?

Which of the following is the more stable carbocation? I thought the 1st carbocation would be the more stable one as the pi-electron density of phenyl group can overlap with the vacant orbital on ...
22k views

Carbocation stability order

I was wondering whether the following order (from here) is correct: In the first inequality, why did 9 hyperconjugations dominated resonance effect of benzene ring? In the last inequality doesn't ...
9k views

Why are sp hybridized carbocations high energy?

You don’t see carbocations on double bonds very much, and here's a good reason: compared to sp3, there is more s character in the orbitals, so the empty orbital is held more closely to the nucleus. ...
86 views

Perpendicular orbitals in aryl and vinyl carbocations? [duplicate]

This point (iv) has been given under reasons for extremely low reactivity of aryl and vinyl halides. I cannot understand it. First of all, isn't the positive carbon atom in phenyl as well as vinyl ...
699 views

Do vinyl cations adopt a classical or non-classical structure?

Whilst reading this question today, I remembered something that I had seen previously here. In the second linked question, @Martin provided a reference to suggest that vinyl cations actually adopt a ...
183 views

Alkenes v/s Alkynes in two different reactions

Alkynes are less reactive towards electrophylic addition than alkenes. However, in case of catalytic hydrogenation, alkynes are said to be more reactive. Why? Also, if I want to add H+ as an ...
271 views

On the stability of carbocations

I have a question regarding the stability of carbocations. It is shown below. I am confused between options II and III. The structure shown in option II has more resonance structures. Thus, I ...
46 views

Stability of the alkenyl and phenyl cations

One reason often cited for why alkenyl and phenyl halides do not undergo nucleophilic substitution by the $\ce {S_N1}$ mechanism is that the formation of the alkenyl and phenyl cations involve a ...
60 views

Organic chemistry, hybridization concept [closed]

Hybridization of phenyl cation and venyl[sic] vinyl cation and acetylene cation ,I am totally confused , I think that the hybridization of both phenyl and the venyl cation is SP , I think that in both ...
42 views

Accounting for Vinylic Carbocation instability [closed]

I read that due to geometrical constraint, positive carbons in an aryl carbocation exhibit sp^2 hybridization instead of sp^1. The empty p-orbital is forced into a hybridized position via geometrical ...
95 views

Why is SN1 mechanism followed in diazo aromatic compounds' nucleophilic substitution?

There is considerable evidence that SN1 mechanism is followed in diazo aromatic compounds' nucleophilic substitution. I would like to know the reason for this and why is it preferred to SNAr mechanism ...