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 257: Problem 6-27 c

Answer

The mechanism will be predominantly SN1 because the carbon with iodine is a tertiary carbon, which is much more likely to undergo SN1 than SN2.

Work Step by Step

Even though ethanol is a strong nucleophile and o=you might think it favors SN2, SN2 is very unlikely to occur at a tertiary carbon.
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