Consider the structure of D-xylose. i. Draw B-D-xylopyranose in Haworth projection. Write the products formed when D-xylose is reacted with: 1. CH,OH, H* 2. (CH;CO);O 3. HNO;

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Chapter1: Chemical Foundations
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QUESTION 2,
а)
Consider the structure of D-xylose.
Draw B-D-xylopyranose in Haworth projection.
Write the products formed when D-xylose is reacted with:
i.
ii.
1.
CH;OH, H*
2.
(CH;CO),0
3.
HNO;
b)
Suggest a synthetic route to synthesize the following compounds.
i.
D-ribitol from D-allose
D-glucaric acid from D-ribose
II.
c)
A disaccharide D is obtained from a-D-allopyranose and B-D-galactopyranose joined by aß-
1,1-glycosidic linkage.
i.
Draw the chair conformation of disaccharide D.
ii.
Classify disaccharide Das reducing or non reducing sugar. Explain your answer.
Give the product formed when disaccharide D is treated with excess CH31, Ag:O.
II.
iv.
Give the name of disaccharide D.
d) Acid hydrolysis of disaccharide E gives equimolar quantities of D-idose and D-mannose.
Disaccharide E also undergoes mutarotation. Methylation of disaccharide E with CH3I, Ag.O
and then hydrolysis with H3O* forms 2,3,4,6-tetra-O-methyl-D-idose and 2,3,6-tri-O-methyl-D-
mannose. Deduce the structure of disaccharide E.
of eikxse
Transcribed Image Text:QUESTION 2, а) Consider the structure of D-xylose. Draw B-D-xylopyranose in Haworth projection. Write the products formed when D-xylose is reacted with: i. ii. 1. CH;OH, H* 2. (CH;CO),0 3. HNO; b) Suggest a synthetic route to synthesize the following compounds. i. D-ribitol from D-allose D-glucaric acid from D-ribose II. c) A disaccharide D is obtained from a-D-allopyranose and B-D-galactopyranose joined by aß- 1,1-glycosidic linkage. i. Draw the chair conformation of disaccharide D. ii. Classify disaccharide Das reducing or non reducing sugar. Explain your answer. Give the product formed when disaccharide D is treated with excess CH31, Ag:O. II. iv. Give the name of disaccharide D. d) Acid hydrolysis of disaccharide E gives equimolar quantities of D-idose and D-mannose. Disaccharide E also undergoes mutarotation. Methylation of disaccharide E with CH3I, Ag.O and then hydrolysis with H3O* forms 2,3,4,6-tetra-O-methyl-D-idose and 2,3,6-tri-O-methyl-D- mannose. Deduce the structure of disaccharide E. of eikxse
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