3, (a) Which one of the following is not a permissible contributing structure? Explain. H₂C H₂C H₂C (b) (c) N-O +N-Ö H₂C =0: B H₂C H₂C H₂C D Rank the three remaining structures in order of their contribution to the resonance hybrid. Explain your reasoning. Using curved arrows, show the electron movement that connects the three resonance contributors. H₂C N=0:

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter15: Benzene And Aromaticity
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Problem 17VC: Azulene, an isomer of naphthalene, has a remarkably large dipole moment for a hydrocarbon (μ = 1.0...
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3, (a) Which one of the following is not a permissible contributing structure? Explain.
H₂C
H₂C
H₂C
(b)
(c)
N-O
+N-O
H₂C
H₂C
B
N=0:
H₂C
H₂C
H₂C
C
Rank the three remaining structures in order of their contribution to the resonance
hybrid. Explain your reasoning.
Using curved arrows, show the electron movement that connects the three
resonance contributors.
N=0
Transcribed Image Text:3, (a) Which one of the following is not a permissible contributing structure? Explain. H₂C H₂C H₂C (b) (c) N-O +N-O H₂C H₂C B N=0: H₂C H₂C H₂C C Rank the three remaining structures in order of their contribution to the resonance hybrid. Explain your reasoning. Using curved arrows, show the electron movement that connects the three resonance contributors. N=0
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