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I have to draw a Newman projection for a molecule, sighting along the bond between a carbon and nitrogen. Given that the nitrogen is behind the carbon from this viewing angle, how would I depict the nitrogen? I know that I cannot draw it as a circle, as that represents carbon, so I am assuming that it is not possible to draw a Newman projection of this molecule from this particular angle. Is that a valid assumption?

And, if that is true, what would be considered an acceptable answer to that question? Should I just draw a standard 3D structure from the proposed viewing angle?

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    $\begingroup$ The forward atom is represented as a dot. The atom farther back is the circle. $\endgroup$ – Zhe Apr 17 '17 at 20:07
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If it were up to me, I would:

  1. Draw the nitrogen atom as if it were carbon but label it as "N".

  2. Assuming normal valence (e.g. an amine but not a nitro conpound), include the formally nonbonded electron pair as one of the substituents on nitrogen.

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You can just draw the nitrogen from the centre of the circle using a lesser "wedge" angle on the circle to indicate an eclipsed bond.

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