Chapter 14: Problem 6

Experimentally, we find that all six \(\mathrm{C}-\mathrm{C}\) bonds in benzene have the same bond energy, \(509 \mathrm{~kJ} / \mathrm{mole}\). Is this fact more consistent with the bond orders predicted by the Lewis structure or with the calculated bond orders for benzene?

Short Answer

Expert verified

The uniform bond energy of benzene's Carbon-Carbon bonds is more consistent with the calculated bond orders according to the resonance structure of benzene, rather than the alternating bond orders predicted by the Lewis Structure.

Step by step solution

Understand Lewis Structure

Consider the structure of benzene according to the Lewis model. Benzene is a six-membered ring of Carbon atoms, each one also bonding to a Hydrogen atom. According to the Lewis structure, there are alternating double and single C-C bonds. The C-C single bond has a bond order of 1, and the C=C double bond has a bond order of 2.

Understand Resonance Structure

The resonance structures of benzene is a more accurate representation of its structure. The resonance structure suggests that electrons are delocalized evenly across all the carbon atoms in the ring. This implies an equal distribution of bonding character, resulting in all six C-C bonds having the same bond energy.

Compare Lewis and Resonance Structures with Given Bond Energy

The existence of uniform bond energy (509 kJ/mole) for all C-C bonds in benzene suggests equal bond character across the ring. This is inconsistent with the Lewis structure where bond orders alternate between single and double bonds. It is however consistent with the resonance structures, where the bond character is evenly dispersed, leading to all bonds having the same energy.

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Experimentally, we find that all six \(\mathrm{C}-\mathrm{C}\) bonds in benzene have the same bond energy, \(509 \mathrm{~kJ} / \mathrm{mole}\). Is this fact more consistent with the bond orders predicted by the Lewis structure or with the calculated bond orders for benzene?

Short Answer

Step by step solution

Understand Lewis Structure

Understand Resonance Structure

Compare Lewis and Resonance Structures with Given Bond Energy

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