H,C-N=N: H2C=N=N: H2C-Ñ=N: A B

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter5: Stereochemistry At Tetrahedral Centers
Section5.5: Sequence Rules For Specifying Configuration
Problem 8P
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Consider Lewis formulas A, B, and C:

(a) Are A, B, and C constitutional isomers, or are they resonance contributors?
(b) Which have a negatively charged carbon?
(c) Which have a positively charged carbon?
(d) Which have a positively charged nitrogen?
(e) Which have a negatively charged nitrogen?
(f) What is the net charge on each?
(g) Which is a more stable structure, A or B? Why?
(h) Which is a more stable structure, B or C? Why?
(i) What is the CNN geometry in each according to VSEPR?

H,C-N=N:
H2C=N=N:
H2C-Ñ=N:
A
B
Transcribed Image Text:H,C-N=N: H2C=N=N: H2C-Ñ=N: A B
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