Organic Chemistry (8th Edition)

by Wade Jr., L. G.

Published by Pearson

ISBN 10: 0321768418

ISBN 13: 978-0-32176-841-4

Chapter 23 - Carbohydrates and Nucleic Acids - Problems - Page 1115: Problem 23-16

Answer

The mechanism for the base-catalyzed epimerization of erythrose to a mixture of erythrose and threose is shown in the attached image below.

Work Step by Step

The planar enolate can be protonated from either side, producing a mixture of erythrose and threose.

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