Sometimes the nitro group is drawn incorrectly by biologists as shown below on t

Question

Sometimes the nitro group is drawn incorrectly by biologists as shown below on the left. What's attractive about this structure is that the formal charge is zero on each atom. What is incorrect about the lower left structure? Explain the rationale/theoretical underpinning of this "rule." The separation of the ortho and para isomers of bromonitrobenzene relies on differing solubility in 95% ethanol. As stated in the reading for the lab, the ortho isomer is more soluble than the para isomer in 95% ethanol. Explain the differing solubilities of the isomers in 95% ethanol.

Explanation / Answer

Post lab 1

The structure on the left has four bonds to the Nitrogen atom which exceeds its normal valency and thus it should have a net +1 formal charge on it. This is not shown in the structure and thus it is incorrect.

Post lab 2

Ortho bromonitrobenzene is more polar than the para bromonitrobenzene. This is due to the electronic effect shown by Bromo group which increases the polarity of the resulting isomer when closest to the -NO2 group. As distance invcreases between the two groups from ortho to para, the electronic effect goes down and thus polarity also decreases from ortho to the para isomer.

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