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 249: Problem 6-23 a

Answer

2-Bromopropane will react faster by the $S_N1$ mechanism.

Work Step by Step

We know that the structure which forms a more stable carbocation will react faster by the $S_N1$ mechanism. In the given pair, 2-Bromopropane will form a $2^\circ$ carbocation, which is more stable. So, 2-Bromopropane will react faster by the $S_N1$ mechanism.
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