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 - Study Problems - Page 281: 6-52 c (iv)

Answer

The resulting products are (E)-5-ethoxypent-2-ene and (E)-4-ethoxypent-2-ene.

Work Step by Step

First, the given reactant converts into the corresponding unstable primary carbocation which can give two possible outcomes. One of them is the direct reaction with EtOH followed by deprotonation, giving rise to the (E)-5-ethoxypent-2-ene formation. The second path proceeds through a 1,2-hydride shift which leads to the formation of a resonance-stabilized allylic carbocation. As the resulting allylic carbocation is symmetric, EtOH attack followed by deprotonation leads to the formation of (E)-4-ethoxypent-2-ene.
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