Worksheet of Carbohydrates

WORKSHEET OF CARBOHYDRATES
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.
1
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. The reaction of D-ribose with an equivalent of methanol plus HCl forms four
products. Give the structures of the products.
13. Another hexose gives the same aldaric acid on oxidation as does D-glucose.
Which one?
14. 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.
2
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.
19. 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?
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 -D-
glucose 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, 2,3,4-tri-O-
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?
3
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-O-
methyl-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 Benedict’s
reagent? Why?
(a) D-Galactitol (see structure in margin) (d) D-Fructose
(b) L-Arabinose (e) Lactose
(c) 1,3-Dihydroxyacetone (f) Amylose
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WORKSHEET OF CARBOHYDRATES

1. Classify the following monosaccharides:

2. L-(-)-Arabinose is a naturally occurring L sugar. It is obtained by acid hydrolysis of the

3. Name the following sugar:

4. Write Haworth formulas corresponding to the furanose forms of each of the

10. Identify the following sugars:

11. Answer the following questions about the eight aldopentoses:

21. Calculate the percentages of -D-glucose and -D-glucose present at equilibrium

22. Predict whether D-altrose exists preferentially as a pyranose or a furanose. (Hint:

29. Devise a method to convert D-glucose into D-allose.

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