I am supposed to construct the major resonance structures of methyl azide, $\ce{CH3N3}$. I know that in compounds such as the carbonate anion $\ce{CO3^2-}$, resonance can be depicted by interconverting single and double bonds:

Resonance structures of carbonate anion

Is something similar happening with methyl azide but with nitrogens instead of oxygens? e.g.

(Incorrect) resonance structures of methyl azide

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    $\begingroup$ You have the wrong structural isomer. $\endgroup$ – Jan Nov 13 '16 at 23:21
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    $\begingroup$ Think about the azide again. Hint: Sodium azide ($\ce{NaN3}$ hydrolyzes to $\ce{Na+}$ and $\ce{N3-}$. At the moment, your methyl azide looks like a disfigured guanidine ;-) $\endgroup$ – Klaus-Dieter Warzecha Nov 14 '16 at 6:18

Your Y-shaped structures somewhat resemble guanidine, $\ce{HN=C(NH2)2}$. For an exercise on resonance structures, its protonated form, the guanidinium cation, would be an interesting case and you might want to give it a try too.

Methyl azide, however, looks completely different.

  1. As the name suggests, there should be a methyl group, $\ce{CH3}$, and an azide group.

  2. Draw the linear azide anion, $\ce{N3-}$.

    azide anion

  3. Where would a "$\ce{CH3+}$" go?
    Is methyl azide, $\ce{CH3N3}$, a linear molecule?

  4. Draw the resonance structures for methyl azide.

    methyl azide


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