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Chapter 28: Question 28.25 (page 1132)

What two aldoses yield D-xylose on Wohl degradation?

Short Answer

Expert verified

Answer

D-iodose and D-gulose are the two aldoses that yield D-xylose on Wohl degradation.

Step by step solution

01

Aldoses

Aldoses can occur in different forms. Some of them include D and L forms.In the Fischer projection, aldoses with alcohol groups located on the right are D-aldoses. L-aldoses constitute aldoses where the alcohol group is situated on the left.

02

Wohl degradation

The Wohl degradation is a procedure that reduces an aldose chain's length. In this process, aldohexose is transformed into aldopentose. The molecule D-glucose can be converted to D-arabinose by Wohl degradation.

03

Aldoses that yield D-xylose on Wohl degradation

The aldoses that produce D-xylose on Wohl degradation are D-iodose and D-gulose. The structure of the aldoses are given as:

Aldoses producing D-xylose on Wohl degradation

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Most popular questions from this chapter

Drawthe products of each reaction.

(a.)

(b.)

What products are formed when each compound is subjected to a Kiliani鈥揊ischer synthesis?

(a.)

(b.)

Draw the products formed when 尾-D galactose is treated with each reagent.

a.data-custom-editor="chemistry" Ag2O+CH3I

b.data-custom-editor="chemistry" NAH+C6H5CH2Cl

c. The product in (b), then

d.data-custom-editor="chemistry" Theproductin(b.)andH3O+

e. data-custom-editor="chemistry" Ac2O+pyridine

f. data-custom-editor="chemistry" C6H5COCl+pyridine

g. The product in (c), then data-custom-editor="chemistry" C6H5COCl+pyridine

The most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the 伪or尾 anomers of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.

Convert each Haworth projection in Problem 28.14 to a three-dimensional representation using a chair pyranose ring.
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