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OUTPUT · 16:9 · PNGThe diagram presents two complementary representations of the molecular structure of benzene, C6H6. The Kekulé structure shows a six-membered benzene ring with alternating carbon–carbon single and double bonds, while the delocalized model shows that all six carbon–carbon bonds are equivalent. Each carbon atom is bonded to two neighboring carbon atoms and one hydrogen atom. The carbon atoms form a planar regular hexagon, and each is sp2-hybridized. This arrangement produces a strong σ-bond framework in the molecular plane and leaves one unhybridized p orbital on every carbon atom.
The six parallel p orbitals overlap sideways around the entire benzene ring, forming a delocalized π bond above and below the plane of the carbon atoms. Therefore, the π electrons are not confined to three separate carbon–carbon double bonds, even though the Kekulé structure is useful for tracking valence and reactions. Delocalization makes every carbon–carbon bond identical, with a bond length and bond order intermediate between those of typical single and double bonds. The six carbon–hydrogen bonds belong to the planar σ-bond framework and do not participate directly in the delocalized π system.
Use the diagram after reviewing sp2 hybridization and before introducing aromatic reactions. Ask students to count the σ bonds, identify the unhybridized p orbitals, and explain why the Kekulé structure does not predict equal carbon–carbon bond lengths. Students can compare the alternating-bond drawing with the delocalized π model and annotate the electron density above and below the ring. This supports common examination questions on molecular geometry, bond length, bond order, electron delocalization, and the greater stability of benzene compared with a hypothetical cyclohexatriene.
The six π electrons are delocalized over all six carbon atoms rather than localized in three double bonds. Consequently, every carbon–carbon bond has the same bond order, approximately 1.5, and the same intermediate bond length.
The two Kekulé structures are contributing representations that differ only in the positions assigned to the double bonds. The real molecule is not rapidly switching between them; it has one delocalized electronic structure represented by a resonance hybrid.
Each sp2-hybridized carbon uses three hybrid orbitals to form two carbon–carbon σ bonds and one carbon–hydrogen σ bond. Its remaining p orbital overlaps sideways with neighboring p orbitals to create delocalized π electron density above and below the ring.