Organic Chemistry As a Second Language, 3e: First Semester Topics

Published by John Wiley & Sons
ISBN 10: 111801040X
ISBN 13: 978-1-11801-040-2

Chapter 2 - Resonance - 2.3 The Two Commandments - Problems - Page 26: 2.3

Answer

This arrow violates the second commandment.

Work Step by Step

Initially, the nitrogen has 3 bonds and 2 free electrons (1 lone pair). And since nitrogen is an element from the second row of the periodic table, it has to respect the octet rule, so it can't make 4 bonds and have 1 lone pair, as the arrow suggests.
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