You are on page 1of 6

WORK SHEED OF CARBOHYDRATE

1. Classify the following monosaccharides:

2.

L-(-)-Arabinose is a naturally occurring L sugar. It is obtained by acid hydrolysis of the polysaccharide present in mesquite gum. Write a Fischer projection for L-(-)-arabinose.

3. Name the following sugar:

4.

Write Haworth formulas corresponding to the furanose forms of each of the following carbohydrates: (a) D-Xylose (c) L-Arabinose (b) D-Arabinose (d) D-Threose

5. Clearly represent the most stable conformation of the -pyranose form of each of the following sugars: (a) D-Galactose (c) L-Mannose (b) D-Mannose (d) L-Ribose 6. Write the Fischer projection of the open-chain form of each of the following:

7. The specific optical rotations of pure - and -D-mannopyranose are +29.3 and -17.0, respectively. When either form is dissolved in water, mutarotation occurs, and the observed rotation of the solution changes until a final rotation of +14.2 is observed. Assuming that only - and -pyranose forms are present, calculate the percent of each isomer at equilibrium.

8. How many ketotetroses are possible? Write Fischer projections for each. 9. Give the product or products that are obtained when D-galactose reacts with the following: a. nitric acid b. Tollens reagent c. H2/Pd/C d. three equivalents of phenylhydrazine e. Br2 in water f. ethanol + HCl g. product of reaction e (above) + Ca(OH)2, Fe3+, H2O2 10. Identify the following sugars: a. An aldopentose that is not D-arabinose forms D-arabinitol when it is reduced with NaBH4 b. A sugar forms the same osazone as D-galactose with phenylhydrazine, but it is not oxidized by an aqueous solution of Br2. c. A sugar that is not D-altrose forms D-altraric acid when it reacts with nitric acid. d. A ketose, when reduced with H2 + Pd/C forms D-altritol and D-allitol. 11. Answer the following questions about the eight aldopentoses: a. Which are enantiomers? b. Which give identical osazones? c. Which form an optically active compound when oxidized with nitric acid? 12. 13. 14. The reaction of D-ribose with an equivalent of methanol plus HCl forms four products. Give the structures of the products. Another hexose gives the same aldaric acid on oxidation as does D-glucose. Which one? Give the products of periodic acid oxidation of each of the following. How many moles of reagent will be consumed per mole of substrate in each case? (a) D-Arabinose (b) D-Ribose (c) Methyl -D-glucopyranoside (d).

15. Determine the structure of D-galactose, using arguments similar to those used by Fischer to prove the structure of D-glucose. 16. Dr. Isent T. Sweet isolated a monosaccharide and determined that it had a molecular weight of 150. Much to his surprise, he found that it was not optically active. What is the structure of the monosaccharide?

17. D-Glucuronic acid is found widely in plants and animals. One of its functions is to detoxify poisonous HO-containing compounds by reacting with them in the liver to form glucuronides. Glucuronides are water soluble and therefore readily excreted. After ingestion of a poison such as turpentine, morphine, or phenol, the

glucuronides of these compounds are found in the urine. Give the structure of the glucuronide formed by the reaction of -D-glucuronic acid and phenol.

18.

Hyaluronic acid, a component of connective tissue, is the fluid that lubricates the joints. It is an alternating polymer of N-acetyl-D-glucosamine and D-glucuronic acid joined by -1,3-glycosidic linkages. Draw a short segment of hyaluronic acid. In order to synthesize D-galactose, Professor Amy Losse went to the stockroom to get some D-lyxose to use as a starting material. She found that the labels had fallen off the bottles containing D-lyxose and D-xylose. How could she determine which bottle contains D-lyxose?

19.

20. How many aldaric acids are obtained from the 16 aldohexoses? 21. Calculate the percentages of -D-glucose and -D-glucose present at equilibrium from the specific rotations of -D-glucose, -D-glucose, and the equilibrium mixture. Compare your values with those given in previous section. ( Hint: The specific rotation of the mixture equals the specific rotation of -D-glucose times the fraction of glucose present in -form the plus the specific rotation of -Dglucose times the fraction of glucose present in the -form ) 22. Predict whether D-altrose exists preferentially as a pyranose or a furanose. ( Hint: The most stable arrangement for a five-membered ring is for all the adjacent substituents to be trans.) 23. Propose a mechanism for the rearrangement that converts an -hydroxyimine into an -amnioketone.

24.

Write structural formulas for the - and -methyl pyranosides formed by reaction of D-galactose with methanol in the presence of hydrogen chloride.

25. The two stereoisomeric forms of maltose just mentioned undergo mutarotation when dissolved in water. What is the structure of the key intermediate in this process? 26. A disaccharide forms a silver mirror with Tollens reagent and is hydrolyzed by a glycosidase. When the disaccharide is treated with excess methyl iodide in the presence of Ag2O (a reaction that converts all the OH groups to OCH 3 groups)

and then hydrolyzed with water under acidic conditions, methylmannose and 2,3,4,6-tetra-O-methylgalactose are formed. a. Draw the structure of the disaccharide. b. What is the function of Ag2O?

2,3,4-tri- O-

27. All the glucose units in dextran have six-membered rings. When a sample of dextran is treated with methyl iodide and silver oxide and the product is hydrolyzed under acidic conditions, the products obtained are 2,3,4,6-tetra-Omethyl-D-glucose, 2,4,6-tri-O-methyl-D-glucose, 2,3,4-tri-O-methyl-D-glucose, and 2,4-di-O-methyl-D-glucose. Draw a short segment of dextran. 28. When a pyranose is in the chair conformation in which the group CH 2OH and the C-1 OH group are both in the axial position, the two groups can react to form an acetal. This is called the anhydro form of the sugar. (It has lost water.) The anhydro form of D-idose is shown here. In an aqueous solution at 100 C, about 80% of D-idose exists in the anhydro form. Under the same conditions, only about 0.1% of D-glucose exists in the anhydro form. Explain.

29. Devise a method to convert D-glucose into D-allose. 30. Which of the following would be expected to give a positive test with Benedicts reagent? Why? (a) D-Galactitol (see structure in margin) (d) D-Fructose (b) L-Arabinose (e) Lactose (c) 1,3-Dihydroxyacetone (f) Amylose

ooooooooOOOOoooooooo

You might also like