THE UNIVERSITY OF ZAMBIA

SCHOOL OF NATURAL SCIENCES

CHE 3522: Polyfunctional Compounds,
Molecular Rearrangements and Organic Synthesis
Tutorial Sheet 2
October 02, 2023

Instructions: For the week beginning October 09, 2023. Students should submit answers at the
beginning of the tutorial session.

1. In neutral or basic solutions, glycosides do not show mutarotation. However, if the solutions are made
acidic, glycosides show mutarotation. Explain.
2. How might you distinguish between α-D-glucopyranose (i.e., D-glucose) and methyl α-D-
glucopyranoside?
3. Xylitol is a sweetener that is used in sugarless chewing gum. Starting with an appropriate
monosaccharide, outline a possible synthesis of xylitol.

4. Although monosaccharides undergo complex isomerizations in base, aldonic acids are epimerized
specifically at C2 when they are heated with pyridine. Show how you could make use of this reaction
in a synthesis of D-mannose from D-glucose.

5. What products would you expect to be formed when each of the following compounds is treated with
an appropriate amount of periodic acid? How many molar equivalents of HIO4 would be consumed in
each case?
(a) 2,3-Butanediol
(b) 1,2,3-Butanetriol
(c) cis-1,2-Cyclopentanediol

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6. Show how periodic acid could be used to distinguish between an aldohexose and a ketohexose. What
products would you obtain from each, and how many molar equivalents of HIO4 would be consumed?
7. Draw structures for furanose and pyranose forms of D-ribose. Show how you could use periodate
oxidation to distinguish between a methyl ribofuranoside and a methyl ribopyranoside.
8. Osazone formation results in a loss of chirality center at C2 but does not affect other chiral
centers. D-glucose and D-mannose (structures shown below), for example, yield the same
phenylosazone.

(i) Draw the structure of the phenyl osazone formed by these two sugars. (1 mark)
(ii) Provide a mechanism to account for the formation of the phenylosazone in part b(i).
(12 marks)