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 27: 2.11

Answer

This arrow violates the second commandment.

Work Step by Step

Initially, the carbon that will receive the double bond has 4 bonds (since it has a neutral formal charge.) And since carbon is an element from the second row of the periodic table, it has to respect the octet rule, so it can't make 5 bonds, as the arrow suggests.
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