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

In general an electron releasing will be attached to the sp2 carbon and electron attracting group will be attachedto the sp3 carbon.

The reason for lower solubility of p-bromonitrobenzene in ethanol is that it is less polar and the dipole cancels out.

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