Organic Chemistry (8th Edition)

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

Chapter 5 - Stereochemistry - Study Problems - Page 215: 5-26 h

Answer

Convert the Newman projection shown into Fischer projection. The compound is a butane. The 2nd and 3rd carbons are asymmetric carbons.

Work Step by Step

Both asymmetric carbons are of R configuration. Priority for top carbon, Br>NH2>CHFCH3>CH3. This gives R. Priority for bottom carbon, F>CBrNH2CH3>CH3>H. This gives S configuration, but it needs to be reversed because H is in the front. So it should also be R. See image.
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