Chapter 16, Problem 21P

Interpretation Introduction

Interpretation:

The $aldohexoses$ and ketohexoses that are formed when $D-tagatose$ is added to a basic aqueous solution are to be identified.

Concept Introduction:

In the enediol rearrangement of a monosaccharide, the base removes the proton from the $\alpha$-carbon resulting in the formation of enolate ion.  After the deprotonation, enediol is formed resulting in the formation of aldohexose and ketohexose by the base-catalyzed conversion.