This exercise is to determine the reactivity of the carbonyl compounds and

carbohydrates in different tests. For solubility behavior, starch, glucose,

benzaldehyde, and acetone were tested. The polarity of each of these compounds is
the factor that greatly affects the solubility. Benzaldehyde is a nonpolar
monosubstituted benzene ring. The ring contains great electron pi density that is
withdrawn by the aldehyde group attached to the ring making the ring less negative
and non-polar. Comparing the size of the ring and the aldehyde group, the ring is
bigger, therefore its polarity is considered for the whole compound.
Acetone was miscible in water. It is a polar compound due to its short chain Rgroup and its electron rich carbonyl group. Because like dissolved like, this justifies
its solubility. The acetone can form hydrogen bonds with water in which the electron
rich oxygen forms a dipole-dipole attraction with the partially positive hydrogen of
water.
Glucose and starch are also both soluble in water. Since they have many
hydroxyl groups (-OH), this makes them polar molecules and can form H-bonds with
water and are therefore soluble. But, in the case of starch, it was not fully soluble
because it formed a cloudy mixture. This is probably because of large size of the
molecules of the compound and that the amount of water was not enough to
dissolve it.
In benzaldehyde, carbonyl group is attached to the hydrophobic benzene
ring, and this ring is already rich in electron density. Since the carbonyl group
attracts electrons, the electron density of the ring decreases and its polarity is
altered making it nonpolar. Glucose and starch are carbohydrates. They both
contain hydroxyl groups and these groups are electron withdrawing. This electron
withdrawing activity makes their molecules polar.
In the hydrolysis of the disaccharides maltose, lactose, and sucrose and for
polysaccharides cellulose, starch and gum were conducted respectively. The
hydrolyzed forms are the following:
DRAW
In the reaction with 2,4-DNP, the compounds acetone and fomaldehyde were
used. Basically this test is to determine the presence of a ketone or an aldehyde in a
compound. 2,4-DNP reacted with a ketone or an aldehyde will form 2,4dinitrophenylhydrazones. Acetone is a ketone while formaldehyde is an aldehyde, so
both of them had the positive result giving a yellow to orange color of the
precipitate.
DRAW
Same compounds were used in the test with Tollens reagent. Tollens test
was used to determine the chemical reactivity of carbonyl compounds such as
aldehydes and ketones. The main difference between an aldehyde and a ketone is
the presence of hydrogen atom in the carbon bonded to oxygen while in ketones,
there no more free hydrogen atom in the carbonyl carbon. The presence of this
hydrogen atom in fomaldehyde (an aldehyde) makes it more susceptible to be

oxidized- they are strong reducing agents. Basically, this test is to differentiate
aldehyde and ketone. The Tollens reagent contains the diamminesilver(I) ion,
*Ag(NH3)2++. This is made from silver(I) nitrate solution. The addition of a drop of
sodium hydroxide solution gives a precipitate of silver(I) oxide, and then
subsequently adding just enough dilute ammonia solution redissolves the
precipitate. The ammoniacal silver hydroxide is a mild oxidizing agent. The silver ion
is reduced to metallic silver in a positive reaction. Sometimes a silver mirror forms
on the test tube. DRAW
Another test to differentiate compounds is the iodoform test. This test is
specific for compounds that contain methyl ketones. Acetone and hydroxyquinone
were used in the test. Based on the structures (draw), acetone has two methyl
groups while hydroxyquinone has none. The removal of methyl group leads to the
formation of CHI3 which forms the yellow precipitate. The reaction follows:
DRAW
Reaction mechanism: DRAW
General formula: DRAW
Molisch's Test is a sensitive chemical test for the presence of carbohydrates
using Molisch reagent in a solution of alpha-napthol in 95% ethanol, 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
also give colored products) resulting in a red- or purple-colored compound.
Compounds used in this test are glucose, sucrose, starch, and hydroxyquinone.
In the presence of concentrated sulfuric acid, glycosidic linkages are
hydrolyzed to give monosaccharides. Glucose is already a monosaccharide.
nH2O + (C6H10O5)n nC6H12O6
Molisch test is useful for identifying any compound which can be dehydrated
to furfural or hydroxymethylfurfural in the presence of H2SO4. Furfural is derived
from the dehydration of pentoses and pentosans, while hydroxymethylfurfural is
produced from hexoses and hexosans. Since glucose, starch, and sucrose are
carbohydrates, both of them gave a positive result. On the other hand,
hydroxyquinone is a carbonyl compound and not a carbohydrate that is why it gave
a negative result. But sucrose gave a negative result.
DRAW
Benedicts test is used in distinguishing reducing sugars from non-reducing
sugars. Compounds that contain hemiacetal groups are considered as reducing
sugars. Hemiacetal groups are compounds that are derived from aldehydes and
ketones respectively. In the test, Cu2+ is reduced to Cu+ and the reducing sugar is
oxidized to a carboxylic acid. The general reaction is shown below:
DRAW

Compounds used were the hydrolysates in from the hydrolysis. These

hydrolysates products means that they are already converted to their respective
monosaccharide components. The reaction with these respective monosaccharide is
positive because they all contain an OH group in their anomeric carbon making
them as reducing sugars. On the other hand, starch and cellulose were negative in
the test because they are non-reducing sugars. In Benedicts reagent, copper (II)
ions in alkaline solution with sodium citrate added to keep the cupric ions in the
solution. It results in all monosaccharides and most disaccharides reducing the blue
cupric ion to cuprous oxide (Cu 2O) which is a brick red precipitate.
Another test for reducing and non-reducing sugars is the Osazone test. The
products of this test is called osazones. Reducing sugars react positively with
phenylhydrazine. These osazones are yellow, crystalline solids that are useful in
identifying simple sugars. Monosaccharides such as glucose, galactose, and fructose
and disaccharide such as lactose are reducing sugars. This is evident on the
formation of yellow crystalline osazones upon reaction with phenylhydrazine. On the
other hand, sucrose is disaccharide but is not a reducing sugar, thus no osazone
formed.
DRAW structures and the osazones.