Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 8 - Reactions of Alkenes - Problems: Problem 8-21 b


The major product formed is 3-bromo-2-methylbutan-2-ol + enantiomer.

Work Step by Step

The mechanism that gives this product is the addition of Halohydrins: 1) Electrophilic attack forms a bromonium ion. 2) Back-side attack by water on the most substituted carbon opens the bromonium ion. 3) Water removes a proton to give the bromohydrin. The product + the enantiomer is formed.
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