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Nonplanar or Planar Structure of Nitramide

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a) Draw the Lewis structure of nitramide with a single bond between the two nitrogen atoms and include formal charges. Are there any resonance structures? If so, please draw these too. Describe the hybridization of the nitrogen atoms.

b) Using the same atom connectivity as above, draw a Lewis structure with a double bond between the two nitrogen atoms, including formal charges and resonance forms if any. Describe the hybridization of the nitrogen atoms.

c) Which structure (a or b) will be planar and why?

d) According to spectroscopic results, the nonplanar structure is preferred. Is this what you would have predicted from the Lewis Dot structure or not? Explain.

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Solution Summary

This solution includes 2 structural drawings for (a), 1 for (b) and discussion for (c) and (d). 100 words.

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c) Structure b will be planar. Since Na is sp2 hybridized, 0a, 0b and ...

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