Organic Chemistry (8th Edition)

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

Chapter 8 - Reactions of Alkenes - Problems - Page 363: Problem 8-32 a

Answer

The major product is cis-2,3-epoxyhexane.

Work Step by Step

The epoxide ring is form across the double bond. MCPBA epoxidizes an alkene by a concerted electrophilic reaction where several bonds are broken and several are formed at the same time. Starting with the alkene and MCPBA, a one-step reaction gives the epoxide and the acid directly, without any intermediates. Since the reaction happens concerted, the product retains the stereochemistry.
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