Diazomethane Resonance Structure

[Shinpe]

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So I encountered this question in Kaplan. Take a look at it before you readon.











I thought the answer would be c because the negative charge is on the more electronegative atom. But kaplan says it's b. I guess b has the advantage that the +/- charges are less separated but I still thought the Nitrogen having the negative charge would win over. Any other thoughts?

 

[Shinpe]

And ofcourse I forgot to attach the actual question at 5 AM ........

 

[imbenis]

i thought c too..hmmm

 

[ashlander]

octet..?

 

[UCB05]

octet..?

^This. B is the only structure in which all 3 atoms have octets. The carbon in C only has 6 bonding electrons associated with it.

 

[192LT192]

look at C... that carbocation is so so unstable. its not even a primary. it wouldnt form that. i would say C is wrong.

 

[Shinpe]

Oops. I remember now. Full octet definitely comes before negative charge on the more e-negative. Weird how none of the given structures is the actual most stable one (H2C=N=N).....

Thanks