Organic Chemistry (8th Edition)

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

Chapter 8 - Reactions of Alkenes - Study Problems - Page 387: 8-48 f

Answer

The reaction undergoes acid-catalyzed opening of epoxides. The proposed mechanism is shown in the picture.

Work Step by Step

The proposed mechanism is: Step 1: Protonation of the epoxide activates it toward nucleophilic attack. Step 2: Back-side attack by the solvent (water) opens the ring. Step 3: Deprotonation gives the diol product. Then the product is rotated and a fisher projection is made.
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