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 e

Answer

The major product is trans-1,2-cyclodecanediol.

Work Step by Step

1) Epoxide ring is formed using MCPBA. 2) The ring is protonated using an acid. 3) Water comes and attacks the most substituted carbon and opens the ring. 4) Then the water molecule is deprotonoted to give a diol. This reaction yields a trans product, because the hydrogens are on different sides.
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