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: 7.25

Answer

1 - C (Bottom Left) 2 - C (Bottom Right) 3 - C (Top Left) 4 - H
1529762384

Work Step by Step

1. Identify the stereocenter. - And draw the missing hydrogen. 2. List all atoms connected to the stereocenter, and rank them by the atomic number. - C, H, C, C Ranked by atomic number: - C, C, C, H 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: - Top left chain: No variations - Bottom left chain: Double bond on the first carbon. - Bottom right chain: Double bond on the fourth carbon. Therefore, the bottom left chain gets first priority, and the bottom right gets second 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: H, H, H - Bottom right carbon: C, H, H - Bottom left carbon: C, C, H. Since (C>H), the bottom left gets first priority, and the bottom right gets second. ** Double bond: We count the connected atom two times. 4. Put the numbers on the stereocenter atoms: 1 - C (Bottom Left) 2 - C (Bottom Right) 3 - C (Top Left) 4 - H
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