Login processing...

Trial ends in Request Full Access Tell Your Colleague About Jove

16.4: π Molecular Orbitals of the Allyl Cation and Anion

JoVE Core
Organic Chemistry

A subscription to JoVE is required to view this content. Sign in or start your free trial.

π Molecular Orbitals of the Allyl Cation and Anion

16.4: π Molecular Orbitals of the Allyl Cation and Anion

An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with an unhybridized p orbital.

A linear combination of the three atomic p orbitals gives three molecular orbitals, ψ1, ψ2, and ψ3. ψ1 is the bonding molecular orbital, ψ2 is a nonbonding orbital characterized by a node passing through the central carbon, whereas ψ3 is an antibonding molecular orbital with two nodes. The molecular orbital frameworks of the allyl anion and cation are identical and differ only in the number of π electrons. The allyl cation has two π electrons in ψ1, whereas the allyl anion has four π electrons distributed between ψ1 and ψ2.



Molecular Orbitals Allyl Cation Allyl Anion Sp3 Hybridization Sp2 Hybridization P Orbital Bonding Molecular Orbital Nonbonding Orbital Antibonding Molecular Orbital Node Electron Distribution

Get cutting-edge science videos from JoVE sent straight to your inbox every month.

Waiting X
Simple Hit Counter