E2 Regioselective

Background Colour:

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

In an E2 eliminations, the new π bond is formed by overlap of the C-H σ bond with the C-X σ* anti-bonding orbital. The two orbitals have to lie in the same plane for best overlap. E2 elimination takes place from the anti-periplanar conformation, as this is the most stable conformation due to its staggered nature.

E2 elimination

As you can see from the reaction above, when 2-bromobutane undergoes an E2 reaction, two possible stereoisomers are formed. This is because 2-bromobutane has two conformations with H and Br anti-periplanar, but the one that is less hindered forms the major product, so the E-alkene predominates.