Organic Chemistry (8th Edition)

by Wade Jr., L. G.

Published by Pearson

ISBN 10: 0321768418

ISBN 13: 978-0-32176-841-4

Chapter 6 - Alkyl Halides: Nucleophilic Substitution and Elimination - Problems - Page 242: Problem 6-17

Answer

The first step is the protonation of diethyl ether. A lone pair on the oxygen of the ether will attack the H of HBr. The initial products are Br- and CH3CH2-OH-CH2CH3 with + charge on oxygen.

Work Step by Step

The Br- then attacks one of the CH2's to form CH3CH2Br and CH3CH2OH becomes the leaving group.

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