Chapter 23: Question 53 (page 1255)
Draw the following sugar derivatives.
- ethyl--D-glucopyranoside
- 2,3,4,6-tetra-O-ethyl-D-mannopyranose
- 1,3,6-tri-O-ethyl-D-fructofuranose
- Ethyl-2,3,4,6-tetra-O-methyl--D-galactopyranoside
Short Answer
Answer :
Chapter 23: Question 53 (page 1255)
Draw the following sugar derivatives.
Answer :
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Get started for freeQuestion. (a) Figure 23-2 shows that the degradation of D-glucose gives D-arabinose, an aldopentose. Arabinose is most stable in its furanose form. Draw D-arabinofuranose.
(b) Ribose, the C2 epimer of arabinose, is most stable in its furanose form. Draw D-ribofuranose.
(a) Figure 23-2 shows that the degradation of D-glucose gives D-arabinose, an aldopentose. Arabinose is most stable in its furanose form. Draw D-arabinofuranose.
(b) Ribose, the C2 epimer of arabinose, is most stable in its furanose form. Draw D-ribofuranose.
Which of the sugars mentioned in Problem 23-53 and 23-54 are reducing sugars? Which ones undergo mutarotation?
Aldohexoses A and B both undergo Ruff degradation to give aldopentose C. On treatment with warm nitric acid, aldopentose C gives an optically active aldaric acid. B also reacts with warm nitric acid to give an optically active aldaric acid, but A reacts to give an optically inactive aldaric acid. Aldopentose C is degraded to aldotetrose D, which gives optically active tartaric acid when it is treated with nitric acid. Aldotetrose D is degraded to (+)-glyceraldehyde. Deduce the structures of sugars A,B,C and D, and use Figure 23-3 to determine the correct names of these sugars.
When the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of the hydrolysate is found to be tagatose. The following information is known about tagatose:
(1) Molecular formula C6H12O6
(2) Undergoes mutarotation.
(3) Does not react with bromine water.
(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.
(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives 1,3,4,5-tetra-O-methyltagatose.
(a) Draw a Fischer projection structure for the open-chain form of tagatose.
(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatose.
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