R E A C

446
m o d u l a r

l a b o r a t o r y

p r o g r a m

i n

c h e m i s t r y

program editor: H. A. Neidig

Qualitative Testing for Carbohydrates

prepared by James O. Schreck, University of Northern Colorado,
and William M. Loffredo, East Stroudsburg University

Purpose of the Experiment

Study the reactions of various carbohydrates with reagents used to classify
and identify these compounds.

Background Information
The body gets its energy from three main classes of
food: carbohydrates, proteins, and fats. Of these
classes, carbohydrates are the most important
source of energy. When digesting food, the body begins to digest carbohydrates first. This process is relatively efficient, producing waste products that are innocuous (water) or readily removed (carbon dioxide).
Carbohydrates are widely distributed in plant tissues and are even found in certain animal tissues, such
as liver and muscle. Water-soluble carbohydrates often
have a sweet taste and therefore are called sugars.
Another term for carbohydrate is saccharide.
Carbohydrates are actually polyhydroxyaldehydes and polyhydroxyketones, often but not always
with the general formula (CH2O)n, where n equals 3 or
more. We refer to polyhydroxyaldehydes as aldoses
and polyhydroxyketones as ketoses.
Carbohydrates are divided into three general
classes, depending on the number of carbohydrate
molecules they contain. Individual carbohydrate molecules are classified as monosaccharides. Monosaccharides are further classified by the number of

carbon atoms they contain. For example, we call

monosaccharides containing 5 carbons, pentoses,
and those containing 6 carbon atoms, hexoses. Common examples of monosaccharides include ribose, a
five-carbon aldose known as aldopentose; glucose
and galactose, six-carbon aldoses known as aldohexoses; and fructose, a ketohexose.
Carbohydrates containing a few monosaccharide
units are classified as oligosaccharides. Oligosaccharides can be further subdivided into disaccharides
(two-monosaccharide units), trisaccharides (threemonosaccharide units), and so forth. Common examples of disaccharides are sucrose (glucosefructose),
table sugar; maltose (glucoseglucose), corn syrup;
and lactose (galactoseglucose), milk sugar.
Carbohydrates containing a large number of
monosaccharide units are classified as polysaccharides. Of the many known polysaccharides, starch,
cellulose, and glycogen are the most important. All
three are made up of hundreds of thousands of glucose units connected in various patterns. One common characteristic of all oligo- and polysaccharides is
that they can be hydrolyzed to their monosaccharide
units by heating in slightly acidic solution.

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REAC 446/Qualitative Testing for Carbohydrates

CHO
H

C OH

C OH

acidic
dehydrating
medium

C OH

-3 H2O

H
OHC

H
C

O
furfural

CH2OH

(Eq. 1)

ribose (a pentose)

CHO
H
HO
H
H

C OH
C

C OH
C OH

acidic
dehydrating
medium
-3 H2O

H
HOCH2

H
C

CH

O
5-hydroxymethylfurfural

CH2OH
glucose (a hexose)

Figure 1 Hemiacetal formation, showing the

hemiacetal structure in the dotted box and the two
anomers
Aldoses undergo an intramolecular reaction between a hydroxyl group and the carbonyl group. The
result is a cyclic hemiacetal, shown in Figure 1. We refer to the carbonyl carbon involved in the reaction as
the anomeric carbon (C* in Figure 1). At this carbon
atom there are two stereochemical configurations possible, alpha () and beta (). The two molecules containing these configurations are called anomers.
Cyclic hemiacetal anomers are more stable than
the open-chain. Therefore, solutions of aldoses always have a higher concentration of anomers than of
open-chain aldoses. A similar intramolecular reaction
occurs between a hydroxyl group and the carbonyl
group of a ketose to form a hemiketal.
Carbohydrate test reagents can be divided into
three general classes based on the type of reaction involved. One class, dehydrating acids, causes carbohydrates to undergo dehydration, and form either
furfural (from a pentose) as shown in Equation 1 or
5-hydroxymethylfurfural (from a hexose) as shown in
Equation 2.
The presence of furfural or 5-hydroxymethylfurfural can be detected by the addition of one of the
second class of test reagents, called condensation
reagents. These are phenolic compounds that react

(Eq. 2)

with furfural or 5-hydroxymethylfurfural to yield highly

colored products. Reagents included in this class are
Molisch reagent, Bials reagent, and Seliwanoffs reagent. These two classes of reagents are frequently
used together as part of a two-step analysis.
The third class of test reagents consists of solutions containing copper(II) ions. These reagents oxidize certain carbohydrates. Two common reagents in
this class are Benedicts and Barfoeds reagents. We
refer to the carbohydrates that reduce the copper(II)
ions in these solutions to copper(I) oxide as reducing
sugars. Reducing sugars are all aldoses containing
either a free aldehyde group or a cyclic hemiacetal.
Note that under the reaction conditions used in tests
with Benedicts and Barfoeds reagents, -hydroxyketoses will also reduce copper(II) ions, giving a positive
(but incorrect) test result. This is due to the slow conversion of the -hydroxyketone group to an -hydroxyaldehyde group, as shown in Figure 2. The R attached to
the groups in Figure 2 represents the part of the molecule not involved in the reaction.
Disaccharides are oligosaccharides containing
two monosaccharide units joined by an acetal or ketal
linkage. The linkage results from the reaction of the
hemiacetal or hemiketal form of one monosaccharide
O OH
H+ or OHR C C H
H
-hydroxyketone

HO O
R C C H
H
-hydroxyaldehyde

Figure 2 Conversion of an -hydroxyketone to

an -hydroxyaldehyde

REAC 446/Qualitative Testing for Carbohydrates

CH2OH
C

OH H

OH

OH

HO

OH H

OH

OH

HO

-glucose

OH H

OH

OH

-glucose

Figure 3

-H2O
+H2O

-glucose

CH2OH

HO

CH2OH

CH2OH

CH2OH
+

CH2OH

OH H

OH H

OH

OH

HO

OH

(a)

maltose

CH2OH
H

OH C

HO

OH

-H2O
+H2O

CH2OH

-fructose

OH H

HO

OH

CH2OH
C
O

OH C

OH

CH2OH

sucrose

(b)

(a) Formation of a reducing disaccharide; (b) formation of a nonreducing disaccharide

with one of the hydroxyl groups on another monosaccharide. Disaccharides containing a free hemiacetal or
hemiketal, such as maltose in Figure 3(a), are reducing
sugars. Disaccharides containing no free hemiacetals
or hemiketals, such as sucrose in Figure 3(b), are nonreducing sugars. As shown in Figure 3, disaccharide
linkages can be broken by the addition of water. This reaction occurs slowly, but it can be catalyzed by acidic
media.

Identifying Products of Carbohydrate

Condensation Reactions
Many carbohydrates can be identified using condensation reagents, which react with the carbohydrates to
produce highly colored products. The precise nature of
the condensation reaction varies with the carbohydrate under investigation. Often the carbohydrate is
initially dehydrated into smaller saccharide units, using
a dehydrating acid. The smaller units, or molecules,
formed will produce a more highly colored complex
with the condensation reagent, as in Molischs, Bials,
and Seliwanoffs tests. In other cases the carbohydrate must possess certain structural features that allow it to form a condensation product, such as in the iodine and potassium iodide test (I2/KI). The following
section describes two types of condensation reactions: those used to generally classify carbohydrates,
and those used to identify specific carbohydrates.

Molisch test
The Molisch test uses concentrated sulfuric acid
as the dehydrating acid. This acid dehydrates all

carbohydrates, so the test is used to distinguish between carbohydrates and non-carbohydrates. The
dehydration products of carbohydrates, furfural or
5-hydroxymethylfurfural, result from the reaction of
the sulfuric acid with pentoses and/or hexoses (Eq.
1 and 2). These products condense with -naphthol
to yield a purple condensation product. The two-step
process is represented by Equation 3.
carbohydrate dehydration product
purple product

(Eq. 3)

Iodine and Potassium Iodide Test

Starches form deeply colored blue-black complexes with iodine. Starches contain -amylose, a helical saccharide polymer, and amylopectin. Iodine forms
a large complex polysaccharide with the -amylose
helix, producing the blue-black color. Simpler oligosaccharides and monosaccharides do not form this
complex with iodine. Thus, the I2/KI test can be used to
distinguish starches from other carbohydrates.

Bials Test
Bials test uses concentrated hydrochloric acid as
the dehydrating acid and orcinol with a trace of iron(III)
chloride as the condensation reagent. Bials test is
used to distinguish between pentoses and hexoses.
Pentoses subjected to the test yield a blue or green
condensation product, while hexoses yield a muddy
brown-to-gray condensation product, as shown in
Equations 4 and 5.
pentose dehydration product:
furfural

blue or green condensation product

(Eq. 4)

REAC 446/Qualitative Testing for Carbohydrates

hexose dehydration product:

5-hydroxymethylfurfural

muddy brown-gray condensation product

(Eq. 5)

R CHO
reducing + 2 Cu 2 + + 2 H2 O
saccharide
R COOH
carboxylic + Cu 2 O (s, red) + 4 H+
acid
(Eq. 8)

Seliwanoffs Test
Seliwanoffs test uses 6M hydrochloric acid as the
dehydrating acid and resorcinol as the condensation
reagent. Seliwanoffs test is used to distinguish between aldoses and ketoses. When mixed with Seliwanoffs reagent, ketopentoses and ketohexoses react within
2 minutes to form a cherry-red condensation product,
as shown in Equation 6.
ketose dehydration product
cherry-red product

(Eq. 6)

(within 2 min)

Aldopentoses react after 2 minutes to form a blue-green

condensation product, which may further change to a
peach color.

Identifying Reducing Sugars

In this experiment, you will use the various

reagents to test and classify several carbohydrate solutions. You will classify the carbohydrates according
to the number of molecules contained in the structure
and the number of carbon atoms in the carbohydrate
unit. You will also determine whether the carbohydrate
is an aldose or ketose, and whether it is reducing or
nonreducing. A classification flow chart used for carbohydrate identification in this experiment is shown in
Figure 4 on the next page. You must make careful observations of both positive and negative results for
each classification test. Using these observations, you
will qualitatively identify an unknown carbohydrate
solution.

Reducing sugars are oxidized by copper(II) ions in two

other saccharide test solutions: Benedicts reagent, a
mildly basic solution, and Barfoeds reagent, a mildly
acidic solution. The presence of red copper(I) oxide
precipitate indicates that the saccharide has reduced
the copper(II) ions.

Procedure
Chemical Alert
Molisch reagenttoxic and corrosive
iodinepotassium iodide reagenthighly toxic,
corrosive, and irritant
Barfoeds reagentcorrosive and irritant
Bials reagenttoxic and corrosive
Benedicts reagenttoxic and irritant
Seliwanoffs reagenttoxic and corrosive
concentrated sulfuric acidtoxic and corrosive

Benedicts Test
Benedicts test uses a mixture of copper(II) sulfate, sodium citrate, and sodium carbonate in a mildly
basic solution. This reagent is used as a general test
for detecting reducing sugars. If the saccharide is a reducing sugar, it will reduce the copper(II) ions to copper(I) oxide, a red precipitate, as shown in Equation 7.

R CHO
reducing
+ 2 Cu 2+ + 5 OH
carbohydrates
R CO 2
carbohydrate + Cu 2 O (s, red) + 3 H2 O
ion
(Eq. 7)
Barfoeds Test
Barfoeds test uses copper(II) ions in a slightly
acidic medium. If the reaction time is carefully monitored, this test can be used to distinguish reducing
monosaccharides from reducing disaccharides. Reducing monosaccharides cause the formation of copper(I) oxide within 23 minutes. Reducing disaccharides cause the formation of copper(I) oxide after
approximately 10 minutes.

Caution: Wear departmentally approved eye

protection while doing this experiment.

I.

Reacting Known Carbohydrate Solutions

Note: Because test tubes are placed in a boiling-water bath, you will need to label them by
marking the etched glass portion on the tube using either a pencil or marking pen. Do not use paper labels, which can become loose in the hot
water.

1. Label three sets of 7 clean, dry 18 150-mm test

tubes with the names of each of the seven carbohydrate solutions you are testing.

REAC 446/Qualitative Testing for Carbohydrates

Figure 4

Flow chart for classifying an unknown carbohydrate

2. Obtain from your laboratory instructor, and transfer into one set of seven labeled test tubes, 10 mL of
each of the following 1% carbohydrate solutions:
xylose, fructose, glucose, lactose, sucrose, maltose,
and starch.

Molisch Test
Caution: Molisch reagent contains concentrated sulfuric acid, which is toxic and corrosive.
It can cause severe burns. Prevent eye, skin,
clothing, and combustible material contact. Avoid

ingesting the substance. If you spill any reagent

or acid, immediately notify your laboratory
instructor.

Note: Do not place your thumb over the open

end of a test tube when mixing its contents. Your
laboratory instructor will suggest ways in which
you can safely and thoroughly mix the contents of
a test tube.
3. Transfer 2 mL of each of the carbohydrate solutions from the first set of labeled test tubes into the

REAC 446/Qualitative Testing for Carbohydrates

second set. Add 2 drops of Molisch reagent to each

tube in the second set, and mix well with a clean glass
stirring rod.
Add 2 mL of concentrated sulfuric acid to each of
the test tubes in the third set.

Caution: In the next step, you will be adding

aqueous solutions to concentrated sulfuric acid.
You must be extremely careful while performing
this step.

4. One at a time, hold the test tubes containing the

concentrated sulfuric acid at an angle of about 30
from the vertical and slowly pour the carbohydrateMolisch reagent solutions from the second set
of test tubes into them. Do not shake or mix the resulting solutions. Two separate layers will form.

Note: When testing your unknown in Step 5, if

there is no color change at the interface between
the two layers, the test result is negative. Do not
continue the tests for the samples that test negative for the Molisch test.

5. Record your results on Data Sheet 1.

6. Discard the test solutions containing Molisch reagent into the container provided by your laboratory
instructor and labeled Discarded Molisch Reagent
Solutions.
7. Wash the second and third sets of test tubes with
soap or detergent solution. Rinse three times with tap
water and once with distilled or deionized water. Allow
the test tubes to drain in order to remove as much of
the water as possible.

Iodine and Potassium Iodide Test

9. Record on Data Sheet 1 the positive or negative

results that you observe after you mix the solutions
with the I2/KI reagent.
10. Discard the test solutions containing the I2/KI solution into the container provided by your laboratory instructor and labeled Discarded I2/KI Solutions.
11. Wash the test tubes with soap or detergent solution. Rinse three times with tap water and once with
distilled water. Allow the test tubes to drain.

Caution: In the next four tests you will place

the test tubes containing the reaction solutions in
a boiling-water bath. Be careful that you do not
come in contact with the steam or the hot apparatus, and that you do not knock over the bath.
Note: Before using the boiling-water bath, be
sure to add two boiling chips to the beaker of water, in order to prevent the test tubes from bumping as the water boils.
12. To set up a boiling-water bath, place an 800-mL
beaker through an iron support ring small enough that
the lip of the beaker will not pass through it. Clamp the
ring and beaker to a support stand. Place a ceramic-centered wire gauze on a tripod or another iron
ring support under the beaker. If you use a ring, clamp
it to the support stand. Add 350 mL of water to the
beaker, along with two boiling chips. Heat the water to
boiling, using a Bunsen burner flame placed under the
beaker.

Barfoeds Test
Caution: Barfoeds reagent is corrosive and an
irritant. If you spill any of the solution on yourself
or on the bench, immediately notify your laboratory instructor.

Caution: The I2/KI solution is toxic, corrosive,

and an irritant. If you spill any of the solution on
yourself or on the bench, immediately notify your
laboratory instructor.

Note: A red precipitate before 5 min have

elapsed indicates a positive result for a reducing monosaccharide. If a red precipitate appears at about 10 min, the sample is a reducing
disaccharide.

8. Transfer 2 mL of each of your carbohydrate solutions into one set of the washed, drained, labeled test
tubes. Add 2 drops of the I2/KI solution to each test
tube.

13. Transfer 1 mL of each of your carbohydrate solutions into one set of the washed, drained test tubes.
Add 3 mL of Barfoeds reagent to each test tube. Using
a test tube clamp, place the test tubes containing the

REAC 446/Qualitative Testing for Carbohydrates

reaction mixtures in your boiling-water bath. Note the

time on Data Sheet 1. Allow the test tubes to stand in
the boiling-water bath for 5 min. After 5 min, use the
test tube clamp to cautiously remove the hot test tubes
and observe the contents. Replace in the boiling-water
bath for 5 additional minutes any test tubes that have
no red precipitate. Cool under running water any test
tubes that contain a red precipitate. Place the cool test
tubes from the bath in a test tube rack.

21. Add 3 mL of Benedicts reagent to each of the test

tubes in one set. Then transfer 10 drops of each of
your carbohydrate solutions to the appropriately labeled tubes. Using a test tube clamp, place the test
tubes containing the reaction mixtures in the boiling-water bath. After exactly 2 min, use the test tube
clamp to remove the test tubes, and place them in a
test tube rack.

14. Record the time for Barfoeds test on Data Sheet 1.

22. Record all observations and the color of any precipitate on Data Sheet 1.

15. Discard the test solutions containing Barfoeds reagent into the container provided by your laboratory instructor and labeled Discarded Barfoeds Reagent
Solutions.

23. Discard the test solutions containing Benedicts

reagent into the container provided by your laboratory
instructor and labeled Discarded Benedicts Reagent
Solutions.

16. Wash the test tubes with soap or detergent solution. Rinse three times with tap water and once with
distilled water. Allow the test tubes to drain.

24. Wash, rinse, and drain the test tubes as before.

Seliwanoffs Test
Caution: Seliwanoffs reagent is toxic and corrosive. If you spill any of the solution on yourself
or on the bench, immediately notify your laboratory instructor.
17. Transfer 10 drops of each of your carbohydrate
solutions to one set of drained test tubes. Then add 15
drops of distilled water and 9 mL of Seliwanoffs reagent to each test tube. Using a test tube clamp, carefully place the test tubes containing the reaction mixtures in the boiling-water bath. Do not allow the test
tubes to stand in the bath for more than 2.5 min. Use
the test tube clamp to carefully remove the test tubes
from the bath, place them in a test tube rack, and observe the solution color in each one.
18. Record your observations for Seliwanoffs test on
Data Sheet 1.
19. Discard the test solutions containing Seliwanoffs
reagent into the container provided by your laboratory
instructor and labeled Discarded Seliwanoffs Reagent Solutions.
20. Wash, rinse, and drain the test tubes as before.

Benedicts Test
Caution: Benedicts reagent is toxic. If you spill
any of the solution on yourself or on the bench,
immediately notify your laboratory instructor.

Bials Test
Caution: Bials reagent is toxic and corrosive.
Use a fume hood when working with Bials reagent. If you spill any of the solution on yourself
or on the bench, immediately notify your laboratory instructor.
25. Add 3 mL of Bials reagent to each of the test
tubes in one set. Then transfer 2 drops of each of your
carbohydrate solutions to the appropriately labeled
test tubes. Using a test tube clamp, place the test
tubes containing the reaction mixtures in the boiling-water bath. Record the time on Data Sheet 1. Use
the clamp to remove each test tube from the bath as
soon as you see a color change. Place the tube in a
test tube rack and record the time on Data Sheet 1. Do
not allow the test tubes to stand in the bath for more
than 5 min, even if no color change occurs.
26. Record the color change on Data Sheet 1, and
calculate the time it took for the color to change.
27. Discard the test solutions containing Bials reagent
into the container provided by your laboratory instructor
and labeled Discarded Bials Reagent Solutions.
28. Discard your carbohydrate test solutions into the
drain, diluting with a large amount of running water.
Wash, rinse, and drain all of the glassware as before.

Note: Leave the boiling-water bath set up, so

you can use it for the unknown carbohydrate solution in Part II.

REAC 446/Qualitative Testing for Carbohydrates

Identifying an Unknown Carbohydrate

Solution

stop as soon as you have identified your unknown solution. Record all observations on Data Sheet 2.

Note: Each of the tests in Part I distinguishes

between two classes of carbohydrates. It may
not be necessary to perform all of the tests in order to identify your unknown sample in Part II.

Note: If your laboratory instructor asks you to

identify additional unknown carbohydrate solutions, prepare additional copies of Data Sheet 2.

29. Obtain 10 mL of a 1% unknown carbohydrate solution from your laboratory instructor in a washed and
drained, 18 150-mm test tube. The unknown carbohydrate solution will be one of the solutions you tested
in Part I. Label the test tube with the identification code
for the unknown, and record the code on Data Sheet 2.

31. Dispose of your solutions in the appropriate containers. Wash, rinse, and drain any glassware you
have used.

II.

Caution: Wash your hands thoroughly with

soap or detergent before leaving the laboratory.

30. Repeat the tests outlined in Part I, Steps 328,

using your unknown carbohydrate solution. You may

Post-Laboratory Questions
(Use the spaces provided for the answers and additional paper if necessary.)
1. When an aldose reacts with Barfoeds reagent,
what type of organic compound forms? What type of
chemical reaction is this?

2. Explain why fructose, an -hydroxyketose, reacts

with Benedicts reagent. What structural rearrangement is necessary for this reaction to occur?

4. An unknown carbohydrate solution tested positive

with Molisch reagent, formed a red precipitate with
Barfoeds reagent within 3 minutes, and turned
blue-green when mixed with Bials reagent. What carbohydrate is this?

5. Erythrose is a four-carbon aldose. Describe the

results of testing it with the following reagents.
(1) Molisch

(2) Barfoeds
3. Explain what happened when you mixed sucrose
with Seliwanoffs reagent. Was this the result you expected? Briefly comment.

(3) Benedicts

(4) Seliwanoffs

name

section

date

name

section

date

Data Sheet 1
I.

Reacting Known Carbohydrate Solutions

test
reagent

saccharide solution
xylose

fructose

glucose

lactose

sucrose

maltose

starch

Molisch

________

________

________

________

________

________

________

I2/KI

________

________

________

________

________

________

________

Barfoeds
time:
final

________

________

________

________

________

________

________

________

________

________

________

________

________

________

initial

________

________

________

________

________

________

________

elapsed

________

________

________

________

________

________

________

Seliwanoffs
time:
final

________

________

________

________

________

________

________

________

________

________

________

________

________

________

initial

________

________

________

________

________

________

________

elapsed

________

________

________

________

________

________

________

Benedicts
time:
final

________

________

________

________

________

________

________

________

________

________

________

________

________

________

initial

________

________

________

________

________

________

________

elapsed

________

________

________

________

________

________

________

________

________

________

________

________

________

________

________

________

________

________

________

________

________

initial

________

________

________

________

________

________

________

elapsed

________

________

________

________

________

________

________

Bials
time:
final

REAC 446/Qualitative Testing for Carbohydrates

10

REAC 446/Qualitative Testing for Carbohydrates

Data Sheet 2
II.

Identifying an Unknown Carbohydrate Solution

unknown identification code ________________

test reagent

observation

conclusion

Molisch

________________________________

________________________________

I2/KI

________________________________

________________________________

Barfoeds
time:
final

________________________________

________________________________

initial

________________________________

elapsed

________________________________

Seliwanoffs
time:
final

________________________________

________________________________

________________________________

initial

________________________________

elapsed

________________________________

Benedicts
time:
final

________________________________

initial

________________________________

elapsed

________________________________

Bials
time:
final

________________________________

________________________________

________________________________

________________________________
________________________________

initial

________________________________

elapsed

________________________________

________________________________

name

section

date

Pre-Laboratory Assignment
1. Describe the hazards associated with the following test reagents.
(1) Molisch

3. Classify the following saccharides as either reducing or nonreducing sugars.

(1) ribose

(2) Bials

(2) sucrose

(3) Seliwanoffs

(3) hydrolyzed starch

2. Briefly explain the meanings of the following terms

as they relate to this experiment. Include structural formulas if appropriate.
(1) aldohexose

4. For each of the following test reagents, describe

the appearance of the reaction mixture that indicates a
positive result.
(1) iodine/potassium iodide solution

(2) reducing sugar

(2) Benedicts

(3) hemiacetal

(3) Seliwanoffs

REAC 446/Qualitative Testing for Carbohydrates

11

12

REAC 446/Qualitative Testing for Carbohydrates

5. For each of the following test reagents, describe

the class and give a specific example of a carbohydrate that would yield a positive result.
(1) iodine/potassium iodide solution

6. Which test could you use to distinguish between

the following pairs of carbohydrates?
(1) fructose and galactose

(2) ribose and glucose

(2) Benedicts reagent

(3) glucose and maltose

(3) Seliwanoffs reagent

ISBN 0-87540-446-4