Is II a resonating structure of I? [closed]








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Is the structure II a resonating structure of I? If yes, then how? Isn't the lone pair on N non conjugated so as not to participate in resonance? 


I ![Structure I](https://i.stack.imgur.com/qZcfZ.png)
II ![Structure II](https://i.stack.imgur.com/oC1GF.png)




Note that *both* representations contain errors.


Under normal circumstances, the [valence](https://en.wikipedia.org/wiki/Valence_(chemistry)) of uncharged carbon atoms in a molecule equal to four. 


Hence, in the upper representation, the carbon bond to the nitrogen bears one valence to much. Keeping the rest of the structure drawn as close to the original, your first drawing should look like the following:


[![enter image description here](https://i.stack.imgur.com/lJm9U.png)](https://i.stack.imgur.com/lJm9U.png)


In the lower representation, both the carbons binding towards oxygen are depicted as if carbon were pentavalent, which under normal circumstances does not occur. In addition the central atom of nitrogen is drawn as if it were tetravalent. There are instances of tetravalent nitrogen atoms in organic compounds, however these are positively charged (like the [tetrabutylammonium](https://en.wikipedia.org/wiki/Tetrabutylammonium_hydroxide) ion, or the [iminium](https://en.wikipedia.org/wiki/Iminium) cation) on nitrogen. Indeed the second (assuming a motif of $\ce{C=N=C}$) would be something not frequently seen, but *on paper* could be represented for example as 


[![enter image description here](https://i.stack.imgur.com/7vTeI.png)](https://i.stack.imgur.com/7vTeI.png)


 3

There is a carbon atom in the second structure with 5 bonds. It is not a real structure nor a resonance structure of 1


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