Rogeni Misaelle M.

Petinglay Date performed: April 17, 2017

B.S. in Chemistry II Date submitted: April 24, 2017

Experiment No. 10
CARBONYL COMPOUNDS AND CARBOHYDRATES

I. Summary of Results

Table 1. Solubility Behavior

Sample Observations Result
Benzaldehyde Heterogenous solution Insoluble
Starch Homogeneous solution Soluble
Cellulose Homogeneous solution Soluble
Acetone Homogeneous solution Soluble
Glucose Heterogenous solution Insoluble

Table 2. Hydrolysis of Di- and Polysaccharides

Sample Observations Result
Homogeneos, neon pink solution,
Sucrose Hydrolyzed
precipitate formation
Starch Homogeneous, light pink solution Hydrolyzed
Cellulose Gel-like formulation, pink solution Hydrolyzed

Table 3. Chemical Reactivity of Carbonyl Compounds

Reaction with Tollens reagent
Iodoform Test Reaction with 2, 4 DNP
Sample
Observations Result Observations Result Observations Result
Colorless solution ->
Yellow
Colorless solution
2 drops to form a solution with
Acetone with smaller - - +
clear solution yellow orange
precipitates compared
precipites
to acetaldehyde
Colorless solution
Yellow orange
with small black
4 drops to form a solution with
Acetaldehyde particles -> Gray + - +
clear solution orange
solution with small
precipitates
black precipitates
3 drops to form a
two layered
Yellow
solution. Clear
solution with
Cyclohexanone --- bottom layer and - -
neon yellow
oily solution with
precipitates
some emulsions on
the upper layer
Yellow orange
Glucose --- --- -
solution
Yellow orange
Fructose --- --- -
solution
 Yellow orange
solution with
Benzaldehyde --- --- +
yellow orange
precipitates
Note: --- means that it is not a sample in the test

Table 4. Molisch Test

Observations Result
Sample
After shaking After +2ml concentrated H2SO4
Insoluble, oily formulation, Exothermic, 2 layered solution, light
orange upper layer, colorless brown upper layer, brownish red
Cyclohexanone -
with black precipitates bottom bottom layer, formation of brown
layer precipitates
Soluble, formation of black Exothermic, brown precipitates,
Glucose -
precipitates homogenous
Exothermic, homogenous, yellowish
Soluble, formation of black
Sucrose dark brown solution with back -
precipitates
precipitates
Formation of black precipitates,
Soluble, formation of black three layers from top to bottom-
Starch +
precipitates colorless, violet, pale red violet
respectively.

Table 5. Benedicts Test

Observations
Sample Result
Before heating After heating
Brown solution,
Sucrose (hydrolysates) Cloudy and pinkish solution -
decomposition of sucrose
Purple upper layer and Cloudy orange solution,
Starch (hydrolysates) -
indigo bottom layer soluble
Gelatinous dark pink solution
Gel-like and violet with dark pink on surface,
Cellulose (hydrolysates) -
substance white gelatinous solution at
the bottom
Lactose Sky blue solution Cloudy dark orange solution +
Glucose Sky blue solution Cloudy dark orange solution +
Fructose Sky blue solution Cloudy dark brown solution +
Sucrose Sky blue solution Cloudy light brown solution -

Table 6. Osazone Formation

Sample Observations
Fructose Pale yellow with white settled particles, 1 minute and 12 seconds
Lactose Pale yellow with settled insoluble particles, no change after 5 minutes
Sucrose Pale yellow with settled insoluble particles, no change after 5 minutes
Glucose Pale yellow w/ white precipitates and settled white insoluble particles, 3 min and 57 sec
 II. Discussion

A carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen

atom: C=O. It is common to several classes of organic compounds, as part of many larger functional
groups. A compound containing a carbonyl group is often referred to as a carbonyl compound.

Carbohydrates (also called saccharides) are molecular compounds made from just three elements:
carbon, hydrogen and oxygen. Monosaccharides (e.g. glucose) and disaccharides (e.g. sucrose) are
relatively small molecules. They are often called sugars. Other carbohydrate molecules are very large
(polysaccharides such as starch and cellulose).

In this experiment, the chemical properties of carbonyl compounds and carbohydrates was
exmined. The differences in the chemical reactivity of aldehydes and ketones were obseved. Also, some
chemical tests were performed to distinguish the different types of carbohydrates.

In the first part of the experiment, the solubility of selected samples with water was tested. The
samples used were benzaldehyde, starch, cellulose, acetone, and glucose. Based on the experimental
results, benzaldehyde and glucose are insoluble in water while starch, cellulose and acetone are soluble.
These results have a slight deviation with the theoretical results. Theoretically, only cellulose and
bezaldehyde are insoluble and all other samples are soluble in water. Benzaldehyde is a nonpolar
monosubstituted benzene ring which has a great pi electron density. The ring is less negative due to the
presence of carbonyl group, an electron withdrawing group. Thus reducing the polarity of benzaldehyde.
In cellulose, glucose monomers are added to produce linear polymer chains that can align side by side,
favoring interchain hydrogen bonding. It is insoluble in water of its bulkiness and inflexible structure no
only imparts exceptional strength. Acetone is a polar compound due to its short chain R-group and its
electron rich carbonyl group. It can form hydrogen bonds with water in which the electron rich oxygen
forms a dipole-dipole attraction with the partially positive hydrogen of water. The general rule, like
dissolves like justifying why acetone is miscible in water. Both glucose and starch contain many hydroxyl
groups (-OH), this makes them polar molecules and can form H-bonds with water and are therefore
soluble. In general, the chemical structures and polarity of the samples affected their solubility in water.

The second part of the experiment involves hydrolysis of di- and polysaccharides. Hydrolysis
involves breaking of polysaccharides down into their constituent monosaccharide units. In separate test
tubes, each sample was added with water and dilute HCl. The mixtures were heated for 30 minutes and
after cooling, it was neutralized with dilute NaOH, using phenolphthalein as an indicator. As expected, all
the samples gave positive results. Sucrose is a disaccharide and its hydrolysis is catalyzed by dilute HCl.
It was completely hydrolyzed into glucose and fructose. The presence of these two monosaccharide can
be confirmed by Benedicts test. Starch and cellulose are both polysaccharides that have hundreds of
glucose units for starch and thousands of D-glucose units for cellulose. Both are broken down into their
components. The characterization of sugars as reducing or non-reducing gives useful clues as to their
structures. The neutralizalization of each mixture gave a pink solution due to the phenolphthalein used.
Both sucrose and starch made a homogenous mixture while cellulose made a gel-like mixure.

In the third part of the experiment the chemical reactivity of carbonyl compounds was
examined. This involves the reaction with Tollens reagent, iodoform test, and reaction with 2,4-DNP.

In determining the chemical reactivity of carbonyl compounds such as acetaldehyde and ketones,
the Tollens test is used. The reagent consists of a solution of silver nitrate and ammonia. Results show
that acetaldehyde turned into a gray solution with small black precipitates, indicating a positive test. The
reaction of acetaldehyde with Tollens reagent is:
 Acetone failed to turn into a silver mirror which indicates a negative result. In aldehydes, there is
the presence of a hydrogen atom attached to the carbon-oxygen double bond in the aldehyde while
ketones dont have that hydrogen. Aldehydes can be oxidized easily yielding carboxylic acids or their
salts due to the presence of hydrogen atom and they are strong reducing agents. On other had, ketones are
resistant to oxidation.

The iodoform test is used to determine the presence of methyl ketones. In the experiment, all of
the samples gave a negative result. Theoretically, acetone and acetaldehyde should give a positive result
while the negative result is for cyclohexanone A positive result means there showed the appearance of a
yellow precipitate surfaced. Acetone and acetaldehyde contains methyl groups while cyclohexane does
not. The removal of methyl group of ketone from the molecule causes the production of iodoform (CHI3).

The compound 2,4-dinitrophenylhydrazine reacts with aldehydes and ketones to from 2,4-
dinitrophenylhydrazones. Acetone, acetaldehyde and benzaldehyde gave a positive result where the
formation of orange precipitate took place while the rest gave a negative result. For aliphatic carbonyl
compounds, the precipitates will be yellow while in aromatic carbonyl compounds, it will be red.

The last part of the experiment is for examination of the color reactions undergone by
carbohydrates. Molischs test, Benedicts test and osazone formation were performed in this part.

The Molischs test is a general test for the presence of carbohydrates. It is based on the
dehydration of the carbohydrate by sulfuric acid to produce an aldehyde, which condenses with two
molecules of phenol (usually naphthol, though other phenols (e.g. resorcinol, thymol) also give colored
products) resulting in a red- or purple-colored compound. Molisch reagent is a solution of alpha-naphthol
in 95% ethanol. Different test solutions were put in separate test tubes and added with water and
Molischs reagent. After mixing, concentrated sulfuric acid was slowly along the sides of the test tube in
order to not agitate the mixture and to form a bottom layer. In the presence of concentrated sulfuric acid,
glycosidic linkages are hydrolyzed to give monosaccharides.

A positive reaction in Molischs test is indicated by the appearance of a purple ring at the
interface between the acid and test layers. The alpha-naphthol reacts with the cyclic aldehydes to form
purple colored condensation products. Although this test will detect compounds other than carbohydrates,
a negative result indicates the absence of carbohydrates. In the experiment, only starch gave a positive
result while cyclohexanone, glucose and sucrose gave a negative result. Theoretically, glucose, starch and
sucrose should give a positive result while cyclohexanone should give a negative result. Cyclohexanone
gave a negative result since it is a carbonyl compound and not a carbohydrate. Errors in this part may be
due mainly to contamination.

In Benedicts test, Benedict's reagent is commonly used to detect the presence of reducing
sugars, however other reducing substances also give a positive reaction. A positive test with Benedict's
reagent is shown by a colour change from clear blue to a brick-red precipitate. Reducing sugars are
usually detected by Benedicts reagent, which contains copper (II) ions in alkaline solution with sodium
citrate added to keep the cupric ions in the solution. The alkaline conditions of this test causes isomeric
transformation ketoses to aldoses. It results in all monosaccharides and most disaccharides reducing the
blue cupric ion to cuprous oxide (Cu2O) which is a brick red precipitate.
 In the experiment, lactose, glucose and fructose gave a positive result while all the hydrolysates
and sucrose gave a negative result. Hydrolysates are products of hydrolysis which means that they are
already converted to monosaccharides. Theoretically, the hydrolysates of sucrose are glucose and fructose
so they give a positive test for reducing sugars. On the other hand, hydrolysates of starch and cellulose did
not give a positive test. This means that they are nonreducing sugars. Lactose is directly detected by
Benedict's reagent, because it contains a glucose with a free reducing aldehyde moiety, after
isomerization. Although fructose is not strictly a reducing sugar, it is an alpha-hydroxy-ketone, and gives
a positive test because it is converted to the aldoses glucose and mannose by the base in the reagent.
Sucrose contains two sugars (fructose and glucose) joined by their glycosidic bond in such a way as to
prevent the glucose isomerizing to aldehyde, or the fructose to alpha-hydroxy-ketone form. Sucrose is
thus a non-reducing sugar which does not react with Benedict's reagent.

Phenylhydrazine is the chemical compound with the formula C6H5NHNH2. Osazones are a class
of carbohydrate derivatives formed by the reaction of a sugar with phenylhydrazine. An osazone is a solid
derivative of a sugar containing two phenylhydrazone moieties. Tthe rate at which the osazone forms and
the appearance of the precipitate can differentiate between epimeric sugars. Osazones form at different
rates for different sugars: fructose reacts very rapidly, while glucose takes longer to react. The appearance
of the precipitate can also be different. The crystal structure ranges from coarse (for glucose) to very fine
(for arabinose). In the experiment, lactose and sucrose made no changes after a few minutes.
Theoretically, monosaccharides such as glucose and fructose and disaccharide such as lactose are
reducing sugars. This is evident on the formation of yellow crystalline osazones upon reaction with
phenylhydrazine. Sucrose, a nonreducing double sugar of glucose and fructose, gives no osazone. Due to
the absence of a hemiacetal group in sucrose, it is not in equilibrium with the readily oxidized aldehyde or
ketone. And thus, no osazone is formed.

III. Conclusion

Carbonyl groups and carbohydrates have different properties and certain chemical tests must be
performed in order to determine the presence of different types of carbohydrates. The solubility behaviour
of these groups are mainly affected by the polarity and chemical structures of each compound. Hydrolysis
the chemical breakdown of a compound due to reaction with water. The characterization of sugars as
reducing or non-reducing gives useful clues as to their structures.

In determining the chemical reactivity of carbonyl compounds, some of these tests are
useTollens Test is used to differentiate aldehydes and ketones since aldehydes are easily oxidized while
ketones are not. To distinguish an aldehyde or ketone form other functional groups, 2 ,4-
Dinitrophenylhydrazone Test is a useful method. In Iodoform Test, the presence of methyl ketones are
determined by their reaction with iodine in a basic soliution to yield iodofor as a yellow colored
precipitate.

For identifying the color reactions of carboohydrates, different tests are also used. The Benedicts
test is used to determine the presence of reducing sugars. A positive test is indicated by the reduction of
the Cu2+ ion to Cu (I), (Cu2O) which is red brick in color and insoluble. Molisch's Test is a sensitive
chemical test for the presence of carbohydrates, based on the dehydration of the carbohydrate by sulfuric
acid to produce an aldehyde, which condenses with two molecules of phenol resulting in a red- or purple-
colored compound. Osazone test involves the reaction of monosaccharide with phenylhydrazine. All
reducing sugars form oosazones with excess of phenylhdrazine when kept at boiling temperature.

Some errors in the experiment might be due to contamination, human errors and incorrect
proportions.
IV. Answers to Questions

1. Explain the solubility behavior of the samples used based on their chemical structures.
In general, Benzaldehyde has an aromatic ring and a presence of a substituent. The ring has a
greater pi electron density while the substituent takes away electron from the ring making it
less negative. With this mechanism, it made the ring less polar and so benzaldehyde is
insoluble in water. Because of the greater C=O bond in the structure of the acetone, it is polar
and is soluble in water. The positive H atoms are attracted to one of the lone pairs of the
oxygen in acetone forming dipole-dipole attractions thus releasing energy which is sufficient
in breaking the water molecules and acetone bonds and so possible for dissolving with each
other. Glucose and starch are carbohydrates containing OH which are hydrophilic making
these carbohydrates polar and so they form bonds with water making them soluble with it. In
cellulose, glucose monomers are added to produce linear polymer chains that can align side
by side, favoring interchain hydrogen bonding. It is insoluble in water of its bulkiness and
inflexible structure no only imparts exceptional strength.

2. What is the structural requirement for the haloform reaction of the carbonyl compounds.
For the haloform reaction of carbonyl compounds, at least one methyl group is required in
which the there is a cleavage between the carbonyl and methyl which produces carboxylate
ion and a haloform.

3. How would you rate the oxidizability of aldehydes and ketones: easily oxidizable, oxidizable, not
oxidizable? Justify your answer using specific chemical tests.
Aldehydes have a free hydrogen, while ketones does not. This makes aldehydes easily
oxidizable than ketones. The presence of a very strong oxidizing agent is required to oxidize
a ketone. To support this, tollens test can be used. In tollens test, only the acetaldehyde
produced a positive test which is the presence of a silver mirror while acetone did not react to
it. Tollens test is used to distinguish aldehydes from ketones because aldehydes is easily
oxidizable while ketone is not oxidizable. In addition, both aldehyde and ketone are
oxidizable in iodoform test. Positive result is a pale yellow precipitate of triiodomethane
(iodoform).

4. Account for the differences in the reaction of starch, sucrose, and their hydrolysates with
Benedicts reagent.
Sucrose is not a reducing sugar because it does not have a free aldehyde group. Thus making
it unreactive with Benedicts reagent. On the other hand, glucose, fructose and lactose gave a
positive reaction due to their structures. Based on their structures, there are free aldehyde or
ketone groups in which the Benedicts reagent can oxidize to produce a red solution. In the
cellulose, it is color blue indicating only a small presence of reducing sugar because it is
difficult for the polysaccharides to have free aldehyde groups.

5. What is the structural requirement for the reducing property of carbohydrates.

The structural requirement for the reducing property of carbohydrates is that it needs to have
a aldehyde group or ketone group
 6. Give a simple chemical test to differentiate between the following. Show equations for the
reactions.

V. References

Haloform Reaction of Carbonyl Compounds. Retrieved April 20, 2017 from

https://www.coursehero.com/file/p4sn3864/For-the-haloform-reaction-of-carbonyl-compounds-
at-least-one-methyl-group-is/

Carbonyl Compounds and Carbohydrates. Retrieved April 20, 2017 from

https://www.academia.edu/23549159/Carbonyl_Compounds_and_Carbohydrates

Cellulose. Retrieved April 20, 2017 from http://www1.lsbu.ac.uk/water/cellulose.html

The Haloform Reaction. Retrieved April 20, 2017 from

http://www.chem.ucalgary.ca/courses/350/Carey5th/Ch18/ch18-3-2b.html

Osazone Test. Retrieved April 20, 2017 from https://www.slideshare.net/katealyssacaton/osazone-test-

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