Why all the C-C bond lengths of benzene are equal to 1.39Ao
? explain with detailed structure
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Why are all the C−C bond lengths in benzene equal?
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The model of benzene as a hybrid of two resonance structures with equal “weight” makes it look as if the pi electrons were enforcing the hexagonal symmetry (with all C-C bonds and all C-C-C angles equal).
That’s the traditional view, and it’s good enough understanding for pre-meds that just want to pass “orgo”, but the latest theoretical chemistry suggests that the sigma electron framework is even more important in enforcing the symmetry. Think of cyclohexane, which also has six equal C-C bonds and six equal C-C-C angles but is not a hexagon because it’s nonplanar. There is a balance of forces on each atomic nucleus that ensures this equality. The effects of removing one hydrogen from each carbon to get benzene are (1) the ring is now planar, (2) because of that, the carbon atoms are now sp2 hybridized, and (3) as a result, the bonds are shorter. But there is still balanced force on each carbon atom, so they form a regular hexagon. This is true even before we add the pi electrons to the picture. In fact, a careful partition of energies shows that the pi electrons tend to favor bond alternation!
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