-4
$\begingroup$

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

$\endgroup$
  • 1
    $\begingroup$ You have the wrong structural isomer. $\endgroup$ – Jan Nov 13 '16 at 23:21
  • 1
    $\begingroup$ 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
2
$\begingroup$

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

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.