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: 8.14

Answer

The intermediate is on the left of the image:

Work Step by Step

1. Analyze the arrow. - It is breaking the bond between the "Br" and the compound. Therefore, now there will be the compound without the "Br", and the "Br" alone, because they got separated. (Tail) - It is giving the electrons from the bond to the "Br".(Head) 2. Now, let's find the formal charges: "Br": Initially, it had 6 electrons in lone pairs, and it received one new pair from the arrow. So, now it has 8 electrons and no bonds, since a neutral "Br" has 7: "7 - 8 = -1". Therefore, its formal charges is "-1". The carbon that was making the bond with the "Br": Initially, it had 4 bonds and no free electrons, and then it lost a bond. Therefore, it has, now, 3 bonds, and it has a formal charge of "+1".
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