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 8-33

Answer

The proposed mechanism is shown in the picture below. Two enantiomers are formed.

Work Step by Step

1) The lone pairs on the oxygen attack the H in HCl. The Cl leaves with the electrons of the bond between H and Cl. 2) Methanol attacks either carbon and opens the ring to form OH on one carbon. 3) Another methanol comes and deprotonates the methanol attached to the carbon, forming the product. Two enantiomers are formed.
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