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Resonance and Formal Charge

AP Chemistry· difficulty 4/5

Which Lewis structure of NCO−\text{NCO}^- has the most favorable formal-charge distribution?

  • A

    [N ⁣= ⁣C ⁣= ⁣O]−[N\!=\!C\!=\!O]^- with N(+1), C(0), O(-2)

  • B

    [N ⁣− ⁣C ⁣≡ ⁣O]−[N\!-\!C\!\equiv\!O]^- with N(-2), C(0), O(+1)

  • C

    [N ⁣= ⁣C ⁣= ⁣O]−[N\!=\!C\!=\!O]^- with N(-1), C(0), O(0)

  • D

    [N ⁣≡ ⁣C ⁣− ⁣O]−[N\!\equiv\!C\!-\!O]^- with N(0), C(0), O(-1)

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Explanation

Best Lewis: place the negative formal charge on the most electronegative atom (O). N≡C-O−^- gives N(0), C(0), O(-1) — minimal magnitudes and negative on O.

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