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: 7.22

Answer

1 - Cl 2 - C (Top Left) 3 - C (Bottom Right) 4 - C (Bottom Left)

Work Step by Step

1. Identify the stereocenter. 2. List all atoms connected to the stereocenter, and rank them by the atomic number. - C, Cl, C, C Ranked by atomic number: - Cl, C, C, C 3. As we can see, there are 3 equal atoms, there are two methods for finding their order. First Method (Faster): - Find the closest variation on the chains (Double bond, Substituent). - The chain with the closer variation gets priority. In this case: - The top left chain has a (-OH) on the second carbon. - The bottom right chain has a double bond on the second carbon. - The bottom left chain has no variations. ** The top left and the bottom right have variations on the second carbon, but, since (O>C), the top left chain gets first priority. ** Since the bottom left doesn't have variations, it will get last 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 left carbon: C, H, H Bottom right carbon: C, H, H Bottom left carbon: C, H, H ** Since they are equal, we will have to compare the next carbon on the chains. Second top left carbon: O, H, H Second bottom right carbon: C, C, H Second bottom left carbon: C, H, H ** First priority : Top left carbon (O > C) ** Second priority: Bottom right carbon (C > H) 4. Put the numbers on the stereocenter atoms: 1 - Cl 2 - C (Top Left) 3 - C (Bottom Right) 4 - C (Bottom Left)
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