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 e


As shown in the picture, two products will be formed (+ the enantiomers of each of them).

Work Step by Step

For the product on the left the following mechanism will occur: 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. But since there is a presence of $Cl^-$ in the solution from NaCl, chlorine can also attack the most substituted carbon and form the product on the right.
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