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 8 - Mechanisms - 8.3 Drawing Intermediates - Problems - Page 175: 8.17

Answer

The intermediate is on the image below:
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Work Step by Step

1. Analyze the arrows. First arrow (Left): - Tail: It is breaking a "C-O" bond... - Head: to give the electrons pair to an oxygen. Second arrow (Right): - Tail: It is taking 2 electrons from an oxygen... - Head: to form a bond between this oxygen and a carbon. 2. Now, let's find the formal charges: The left oxygen had neutral charge, then it lost a bond (+1), and gained 2 electrons (-2) = -1 formal charge. The other oxygen had (-1) as a charge, then it lost 2 electrons (+2), and formed a bond (-1) = Neutral formal charge.
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