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a weak deactivator

I am having some trouble explaining why the attached molecule is an otho-para director although a weak deactivator. I believe it is because of resonance forms, but that is as far as I have gotten.

Thanks,

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Lets look at the NO2 (-) resonance structures to understand this substitution group which essentially has to "ground" state resonance structures with sp2 geometry where the double bond can be found to equally be assigned to either oxygen. Incidently, I am not finding this substitution group in the five texts and aids that I checked and am wondering if it is stable. You have shown one of the resonance structures in your picture of the attached molecule. The other one I see has ...

Solution Summary

It explains why the specific molecule is an otho-para director although a weak deactivator.

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