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Carbohydrates

ANSWERS TO QUESTIONS

1. Draw the structures of the osazone produced in the experiment.

 Glucose

O
NH2
H OH HN N NH

HO H
H OH
+ NH NH

HO H
H OH
H OH
OH H OH
CH2OH

 Fructose

OH
NH2
O HN N NH

HO H
H OH
+ NH NH

HO H
H OH
H OH
OH
H OH

CH2OH

 Maltose
OH
NH2
H O H HN OH
H H
OH H HN
H O H
OH O
OH
O OH
+ H
OH H H N NH
H OH H N
H O H OH O
OH
H OH H
HO H OHH

HO
 Sucrose (should not be positive result)

2. Arrange the following sugars according to their reactivity with Benedict’s reagent. Explain your answer.
 glucose, fructose, maltose, sucrose, starch
starch< sucrose < maltose < fructose < glucose
Benedict’s test is a test for reducing sugars. All aldoses, or those with an aldehyde group, are reducing sugars,
and this includes glucose. This is followed by fructose, which is still a reducing sugar despite being ketose, because
it can be isomerized to a mixture of aldoses, that is, glucose and mannose. In short, all monosaccharides are reducing
sugars. Disaccharides such as maltose and sucrose are the next in reactivity. Maltose comes first because it is a
combination of two glucose molecules with one of them having an anomeric carbon with an OH group. Sucrose is not
a reducing sugar because its aldehyde groups are in a glycosidic bond, therefore, they are not in an open-chain
structure and are not available. Lastly, polysaccharides such as starch are not reducing sugars.
References
[1] McMurry, J. Organic Chemistry, 9th ed.; Cengage Learning: Boston, 2016. https://doi.org/10.1017/
cbo9781139096782.017.
[2] Morrison, R. T.; Boyd, R. N. Organic Chemistry. 1992.
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3. What are the differences between Benedict’s and Barfoed’s test?

While the alkaline Benedict’s reagent is used to classify sugars as reducing or non-reducing, the slightly acidic
Barfoed’s reagent is a weaker oxidizing agent. It can oxidize monosaccharides and form the red precipitate, but it
will not oxidize disaccharides, therefore it can be used to differentiate the two types of sugars.

References
[1] Seattle Central College. A Study of Carbohydrates http://faculty.seattlecentral.edu/ptran/bastyr/Summer
06/organic/Organic Exp/exp6 A Study of Carbohydrates.pdf (accessed Oct 15, 2019).

4. Can the Seliwanoff’s test be used to differentiate sucrose from fructose? If yes, how?
Seliwanoff’s test is used to differentiate aldoses and ketoses. Additionally, between sucrose and fructose,
fructose has a faster reaction time. The resorcinol in the reagent reacts with it to form a red complex. After some
time of heating, sucrose would eventually hydrolyze and form a red complex as well. Therefore, yes, the two sugars
can be differentiated, and that is by the rate of reaction.

References
[1] Katoch, R. Analytical Techniques in Biochemistry and Molecular Biology; Springer: New York, 2011.

5. Give a possible application of Bial’s test.

Bial’s test is used to differentiate pentoses and hexoses. Specifically, it is a test for the presence of pentoses.
It can also be referred to as orcinol test in the context of biochemistry. The test is used to determine RNA since the
ribose in ribosome is a pentose.

References
[1] Hanson, R. S.; Phillips, J. A.; Gerhardt, P. Chemical Composition. In Manual of Methods for General Bacteriology;
1981; p 349.

6. Draw the hydrolysis product/s of sucrose and starch.

 Sucrose
CH 2OH CH 2OH CH 2OH CH 2OH
O O H2O O O OH
OH OH OH + OH
O CH 2OH OH CH 2OH
OH OH
OH OH OH OH

 Starch
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CH 2OH CH 2OH CH 2OH

O O O
OH OH OH
O O O O
OH OH OH
CH 2OH CH 2OH CH2
O O O
OH OH OH
O O O O
OH OH OH

H2O

CH 2OH CH 2OH CH 2OH CH 2OH

O O H2O O O
OH OH OH + OH
O O OH OH O
OH OH
OH OH OH OH

7. Give a chemical explanation for the role of starch as an antidote for iodine poisoning.
Starch contains a polysaccharide called amylose which can trap iodine in its helix and reduce the toxicity.

References
[1] Mansour, Z.; Guth, E. P. Complexing Behavior of Starches with Certain Pharmaceuticals. J. Pharm. Sci. 1968, 57
(3), 404–411. https://doi.org/10.1002/jps.2600570307.