Chapter 28: Problem 28.44 (page 1148)
Draw the anomer of a monosaccharide epimeric with D-glucose at C2 using a Haworth projection.
Short Answer
Answer


Chapter 28: Problem 28.44 (page 1148)
Draw the anomer of a monosaccharide epimeric with D-glucose at C2 using a Haworth projection.
Answer


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The most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, , in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the or anomers of D-idose. Explain why the more stable conformation has the group in the axial position.
The following isomerization reaction, drawn using D-glucose as starting material, occurs with all aldohexoses in the presence of base. Draw a stepwise mechanism that illustrates how each compound is formed.

Question: Referring to the structures in Figures 28.4 and 28.5, classify each pair of compounds as enantiomers, epimers, diastereomers but not epimers, or constitutional isomers of each other.
a. D-allose and L-allose
b.D-altrose and D-gulose
c.D-galactose and D-talose.
d.D-mannose and D-fructose.
e.D-fructose and D-sorbose
f.L-sorbose and L-tagatose
Question: Assign R,S designations to each stereogenic center in glucose.
Question: Convert each aldohexose to the indicated anomer using a Haworth projection
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