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 7 - Configurations - 7.2 Determining The Configurations Of A Stereocenter - Problems - Page 140: 7.23


1 - O 2 - C (Top right) 3 - C (Bottom left) 4 - H

Work Step by Step

1. Identify the stereocenter. 2. List all atoms connected to the stereocenter, and rank them by the atomic number. - O, H, C, C Ranked by atomic number: - O, C, C, H 3. As we can see, there are 2 equal atoms, there are two methods for finding their order. First Method (Faster): - Find the closest variation in the chain (Double bond, Substituent). - The chain with the closer variation gets priority. In this case: - Top right chain: Methyl on the first carbon. - Bottom left chain: Oxygen on the third carbon. - Therefore, the top right chain gets priority. Second Method: - Compare the atoms connected to each carbon, and if you don't get the answer, them look at the atoms connected to them. In this case: Top right carbon: C, C, H Bottom left carbon: C, H, H - Since (C>H), the top right carbon gets priority, 4. Put the numbers on the stereocenter atoms: 1 - O 2 - C (Top right) 3 - C (Bottom left) 4 - H
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