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 273: Problem 6-40 f

Answer

Although isobutyl chloride is a primary alkyl halide, AgNO3 in ethanol promotes SN1 and E1. For SN1, rearrangement happens to form a more stable carbocation and therefore OEt ends up at a secondary position rather than primary position. The product with OEt at secondary position is more favored.

Work Step by Step

See image for mechanism.
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