E/Z Isomerism

01E/Z Isomerism

Restricted rotation

This section covers how the pi bond restricts rotation about a carbon-carbon double bond and allows E/Z stereoisomers to exist.

Why groups stay fixed around C=C

In stereoisomers, the atoms are joined together in the same sequence but occupy different arrangements in three-dimensional space. Suitable alkenes can therefore exist as E/Z stereoisomers.

Rotation can occur around a carbon-carbon single bond. In contrast, rotation about the planar C=C double bond is restricted.

The π\pi bond comes from sideways overlap between p orbitals on the two carbon atoms. Turning one carbon relative to the other would destroy this effective sideways overlap, so the substituents remain fixed relative to one another.

As a result, different arrangements around the double bond cannot simply interconvert by rotation.

Exam Tip: Explain the origin of E/Z isomerism by linking restricted rotation specifically to the π\pi bond in the C=C group.

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