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For 1,3,5-trinitrobenzene, which statement about the three carbon-nitrogen (C-N) bonds connecting the ring to the nitro groups is correct?

1. All three C-N bonds are of the same length.
2. Two of the C-N bonds are equal but shorter than the third.
3. Two of the C-N bonds are equal but longer than the third.
4. All three C-N bonds are of different lengths.

Correct answer: All three C-N bonds are of the same length.

Solution

In 1,3,5-trinitrobenzene the three nitro groups occupy the 1, 3 and 5 positions, which are all equivalent by the three-fold (C3) symmetry of the molecule. Each C-NO2 carbon experiences an identical electronic environment, so all three C-N bonds are chemically equivalent and therefore have the same length. The same resonance delocalization acts equally on each nitro group.

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