Chemistry · Chapter 20

Benzene, Delocalized

Slide the model from alternating bonds to one shared ring. The six bonds even out at 139 pm, the stability bonus climbs to 152 kJ/mol, and the ring starts refusing to add.

The ring bond lengths are drawn to scale

The benzene ring you are looking at

At the left-hand end of the slider you see the old picture, with long single bonds and short double bonds taking turns. Real benzene sits at the right-hand end.

The numbers

benzene aromatic
Heat released when hydrogen is added
Short bonds (pm)
139
Long bonds (pm)
139
Resonance energy (kJ/mol)
152
Heat on adding 3 H₂
208
Formula
C6H6
Molar mass (g/mol)
78.11

Six p electrons circle the ring. That fits 4n + 2 with n = 1, which is the test a flat ring must pass to count as aromatic.

Addition or substitution

Compare the two routes
Which one does benzene pick?
Addition would break the shared ring and hand back the stability bonus. Substitution swaps one hydrogen out and leaves the ring whole. Try both and watch the bonus.

Name a substituted ring

Group on carbon 1
Second group
Where the second group sits

Common name: benzene is its own common name.