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 6 - Conformations - 6.2 Ranking The Stability Of Newman Projections - Problems - Page 112: 6.14

Answer

Starting from a point connected to the back carbon (behind the circle), the clockwise or counterclockwise order for the most stable should be: (Me)-(Me)-(H)-(Me)-(H)-(H). And for the least stable: (Me)-(H)-(H)-(Me)-(H)-(Me)

Work Step by Step

1. For both most and less stable conformations, draw the atoms/groups connected to the back carbon. (Represented by the circle.) In this case:* Up: (Me) Right:(H) Left:(H) 2. Identify the largest group connected to the front carbon, and for the back carbons: In this case: Front carbon: Methyl Back carbon: Methyl 3. Now, for the most stable one, we will rotate only the groups/atoms on the front carbon (The point on the center.), trying to put the largest groups we identified as distant as possible. In this case, the front carbon will have:* Down: (Me) Right: (Me) Left: (H) 4. Now, for the most stable one, we will rotate only the groups/atoms on the front carbon (The point on the center.), trying to put the largest groups we identified as close as possible. In this case, the front carbon will have:* Up: (Me) Right: (H) Left: (Me) * This is just an example, but if your drawing isn't equal, it should be at least a rotation of this drawing.
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