Comments on: Exploring Resonance: Pi-acceptors

By: Emma

Emma — Mon, 12 Feb 2018 14:40:47 +0000

In reply to steve. I believe it is because it fulfills the octet rule in the “best” structure, while the second best is a tertiary carbocation.

By: James

James — Wed, 12 Feb 2014 15:22:48 +0000

In reply to steve. The difference should be quite small. One could make the argument that the form on the right has a more substituted double bond, so it should make a greater contribution to the resonance hybrid. I'll see if I can find someone to calculate the difference in stabilization energies.

By: Vlad

Vlad — Tue, 11 Feb 2014 19:34:03 +0000

In reply to steve. Yeah, the one in the left is clearly more stable as it is a tertiary carbocation, while the "second best" on the right has a primary carbocation, which is very unstable. I wonder this question too.

By: steve

steve — Tue, 05 Feb 2013 16:38:14 +0000

Disregarding the reaction conditions, why isn’t the left resonance form in the first figure more stable? The carbocation in “second best” is more substituted than the carbocation in the “also second best” structure.

By: Resonance in Organic Chemistry: Pi Donors and Pi Donation — Master Organic Chemistry

Sun, 18 Mar 2012 04:29:27 +0000

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