Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 6 - Alkyl Halides: Nucleophilic Substitution and Elimination - Problems - Page 245: PRoblem 6-20 c

Answer

The nucleophile I- attacks the top carbon and Br- leaves. Originally, the top carbon has R configuration. The product should have S configuration because SN2 reaction inverts the configuration.

Work Step by Step

I has to be in the back, CH3 gets pushed to the front so that the configuration is S. See image.
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