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EXPERIMENT 10
I. Introduction
II. Methodology
Sample Solubility in
Observation Homogeneity
H2O
(-) (-)
Top layer: clear liquid
Legend:
Solubility in H2O
(-) - insoluble
Homogeneity
(+) - homogeneous
(-) - non-homogeneous
1. acetaldehyde silver
2. acetone none
Legend:
Miscibility
(+) - miscible
(-) - immiscible
1. benzaldehyde orange
2. cyclohexanone orange
3. fructose yellow
4. glucose yellow
5. acetaldehyde orange
1. Sucrose +
2. Cyclohexanone -
3. Glucose +
4. Starch +
The experiment consisted several tests that aimed to distinguish one class of
compound to another by understanding the chemistry of each and the reactions it
undergoes. First part of the experiment focused on the solubility behavior of different
representative compounds. Results showed that all the samples except
benzaldehyde, which represents the aldehyde group, remained insoluble. The
solubility of glucose, starch, and cellulose was due to the presence of oxygen which
introduced partial charges with its high electronegativity. In the case of acetone, which
is a ketone, not only the presence of oxygen but the pi bond that introduced hydrogen
bonding between the compound and water molecule. Meanwhile, benzaldehyde
although it contains carbon doubly bonded to oxygen was not solvated because of the
nonpolar aromatic ring attached to the carbonyl group. As governed by the theory,
like dissolves like, the solubility behavior of different representative compounds for
carbohydrates and carbonyl group also depend on the strengths of the intermolecular
forces of attraction present among the solute, the solvent and between the solute and
the solvent. The domination of carbon and the absence of electronegative elements
promotes insolubilty in polar solvents such as water.
Chemical reactivity of carbonyl compounds was identified with the use of different
tests namely, Tollens test, Iodoform test, and Reaction with
2,4-Dinitrophenylhydrazine. Each class of compound react differently making it
possible for the experimenters to distinguish one class from the other.
Tollens test is governed by oxidation. Silver ion, a weak oxidizing agent, oxidizes
aldehyde to the corresponding carboxylic acid and, in turn, is reduced to metallic
silver which is deposited on the walls of the test-tube such as a mirror. Ketones are
not usually oxidized by the reagent, which significantly indicated that the silver ion in
the tollens reagent is not strong enough to oxidize acetone. As a result, the test tube
with acetaldehyde became a silver mirror and the one with acetone remained to be a
clear liquid with small bubbles. The chemical equation below shows the reaction
between the aldehyde and the Tollens reagent.
Based on the structure of aldehyde, the hydrogen atom directly bonded to the
carbonyl carbon makes it more reactive to oxidation than ketones, which have
R-groups attached to it instead of hydrogen requiring severe conditions in order to
oxidize.
Iodoform test is another test done in this experiment which is commonly used to
test the presence of methyl ketones. Results showed that only in cyclohaxanone and
barely in acetaldehyde did the reaction occur. Other ketones are not capable of
reacting with iodine as proven by the results for acetone. The reaction was very
selective and only occurred for compounds with structures similar to that of methyl
ketones.
The chemical equation above shows the oxidation of methyl ketone with iodine, as the
oxidizing agent, in aqueous sodium chloride. This yields carboxylic acid and the solid
yellow iodoform. Cyclohexanone showed a very clear positive result as expected
since it is a methyl ketone. However, aldehyde only given off a faint yellow color
solution and when heat was applied the color intensified and some iodoform were
formed eventually indicated the occurrence of the reaction. Acetone did not react at all
as indicated by the disappearance of iodine color and the colorless and clear resulting
solution.
Color reactions of carbohydrates included three test; Molisch test, Benedicts test
and Osazone formation. All the three tests used color to indicate the occurrence or the
absence of the reaction. Molisch test is used for carbohydrates larger than tetroses is
based on the dehydration of the carbohydrate by sulfuric acid to produce an aldehyde.
Pentoses are dehydrated to form furfural which is the top reaction while hexoses are
dehydrated to form 5-hydroxymethyl furfural, the bottom reaction. The furfurals further
react with -naphthol present in the test reagent to produce a purple product. The
figures below show the reaction for the dehydration of pentose and hexose. (Neither
of the two were used as samples.)
Among the four samples tested, cyclohexanone was the only sample that did not have
the purple color in the resulting solution. This is because of the nature of the sample
which is a ketone. Ketones can not form furfurals that would react to produce the
purple layer. Meanwhile, the sucrose, glucose, and starch, all had a purple layer in
their final solutions. The three samples are carbohydrates that are larger than tetroses
which indicated the capability of the samples to react with the Molisch reagent (10%
naphthol in ethanol).
Lastly, the osazone formation involved the reaction of ketoses and aldoses with
phenylhydrazine in order to yield phentlhydrazone which further reacts with another
two molecules of phenylhydrazine to produce osazone. Resulting solutions were all
yellow colored liquid and precipitates. The shape of the precipitates vary depending
on the size of the carbohydrate. The test is also used to determine the reactivity of the
carbohydrate. Based on the results, fructose had the shortest time indicating that it
was the most reactive followed by glucose, lactose and least reactive was sucrose.
Results implied that smaller molecules are more reactive as compared to the larger
molecules.
IV. Conclusion
Carbohydrates, on the other hand, are class of natural compounds that contain
either an aldehyde or a ketone group and many hydroxyl groups, and are often called
polyhydroxy aldehydes or ketones. These can be classified as monosaccharides,
disaccharides or polysaccharides. OH molecules in carbohydrates are hydrophilic that
makes the carbohydrates polar and form bonds with water making them soluble with it.
Hydrolysis of non-reducing di-saccharides is catalyzed by strong acids and certain
enzymes. Furthermore, polysaccharides are hydrolyzed by specific enzymes based
on the type of linkage in the polysaccharide.
Ketones are not usually oxidized by the tollens reagent, which is significantly
indicated by silver ion. Iodoform test was done to test the presence of methyl
ketones. The reaction was very selective and only occurred for compounds with
structures similar to that of methyl ketones. The samples in the experiment were also
subjected to 2,4-dinitrophenylhydrazine in order to test for the presence of the
carbon-oxygen double bond. Yellow and orange precipitates were obtained and both
indicated the presence of carbon-oxygen pi bond.
Molisch test is used for carbohydrates larger than tetroses is based on the
dehydration of the carbohydrate by sulfuric acid to produce an aldehyde. Benedicts
test is basically used to determine whether or not the carbohydrate contains a free
aldehyde or ketone group. The carbohydrates that react positively are reducing
sugars. The test is also used to determine the rate of reactivity of the carbohydrate.
Minor variations, in some experimental results, with the theoretical results are
possibly due human error. However, in general, the objectives of this experiment were
met. The experimenters were acquianted with the chemical properties of carbonyl
compounds and carbohydrates. The experimenter also observed the differences in
the chemical reactivity of aldehydes and ketones, and applied the chemical tests that
can distinguish the different types of carbohydrates.
V. References:
Fox and Whitesell, 3rd Ed. Chapter 13 section 13.1 (643-644). (2007). Reactions of
Aldehydes and Ketones. Retrieved 26 2017