Ochem question

[nontradpremed2024]

Can someone please explain to me why B would be higher energy than C?

I got this question wrong because I thought that the oxygen, being quite electronegative, would not be able to hold that positive charge very well at all and would be even higher energy than the secondary carbocation. When I asked the professor about it, he was very difficult to understand--he basically said that the OH2+ would be very fleeting since it could easily donate a proton. However, that's basically what I thought--that it would be very unstable and would quickly donate a proton because it's high energy.

I know that carbocations are highly reactive/unstable/high energy, and the one labeled B is a secondary carbocation, but I would like to understand why that's less stable/more energetic than C.

Thank you!!

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[ClashRoyaleKing]

B is less stable because the carbocation does not have a full octet. The oxycation is more stable with its full octet + being able to draw electron density from the hydrogen and carbons that it is bonded to.

 

[nontradpremed2024]

B is less stable because the carbocation does not have a full octet. The oxycation is more stable with its full octet + being able to draw electron density from the hydrogen and carbons that it is bonded to.

Thanks, this was clear and helpful!

 

[ClashRoyaleKing]

Thanks, this was clear and helpful!

I'm glad to help. I love chemistry.