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 - 2.6 Drawing Resonance Structures - Step by Step - Problems - Page 37: 2.30

Answer

The structure should look like this:

Work Step by Step

1. To form a resonance structure, you can break the double bond by moving one of the bonds to form a lone pair with the oxygen. Show this step by using a curved arrow from the double bond to the oxygen. Remember that the tail of the curved arrow shows where the electrons are coming from and the head of the curved arrow shows where the electrons are moving to. 2. Put in the formal charges created as a result of this move. Oxygen will now have a formal charge of -1 and carbon will now have a formal charge of +1. 3. To make a second resonance structure, move the lone pair on nitrogen to form a double bond with the bond connecting nitrogen to carbon using curved arrow notation. 4. Put in the formal charges created as a result of this move. Oxygen will continue to have a formal charge of -1. Nitrogen now has a +1 formal charge instead of carbon.
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