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 (iii)

Answer

The resulting product is (E)-4-ethoxypent-2-ene.

Work Step by Step

First, the given reactant undergoes a first-order ionization which leads to the formation of a resonance-stabilized carbocation. As the resulting carbocation is symmetric, only one product can be obtained after the EtOH attack followed by deprotonation, this being (E)-4-ethoxypent-2-ene, as shown below.
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