EXPERIMENT 8

CARBONYL COMPOUNDS AND CARBOHYDRATES

In Partial Fulfillment for the Requirements in Chem 31.1

Submitted by:

Hannah Rose Azucena

Elizalde Miguel Flores

Brett Andreil Remegio

Submitted to:

Mr. Mark Lester G. Viendo

Instructor

May 8, 2017
I. Introduction

The carbonyl group is a functional group composed of a carbonatomdouble-bonded to an

oxygen atom C=O.The carbonyl group (C=O) is a source of numerous important reactions in

organic chemistry; mainly a result of the polarization of the carbon-oxygen-π-bond due to the

relatively high electronegativity of the oxygen atom. The carbonyl functional group also acts to

increase the acidity of any hydrogens on carbons directly attached to the carbonyl group (α-

hydrogen atoms). This enhanced acidity means that the α-carbon atom can become nucleophilic,

either through deprotonation reaction to form an enolate ion or by keto-enol equilibration

(tautomerization) to form the enol. Enolates or enols can then react with electrophiles at the α-

carbon to give a net substitution reaction of the electrophile for the α-hydrogen (University of

Western Ontario, 2012).

Carbohydrates are the sugars, starches and fibers found in fruits, grains, vegetables and

milk products. Simple carbohydrates contain just one or two sugars, such as fructose (found in

fruits) and galactose. These single sugars are called monosaccharides. Monosaccharides are the

simplest carbohydrates and are often called single sugars. Monosaccharides have the general

molecular formula CnH2nOn. On the other hand, carbohydrates with two sugars such as sucrose,

lactose, and maltose are called disaccharides. These compounds have two carbohydrate

molecules and are soluble in water just like monosaccharides. An oligosaccharide is a

saccharidepolymer containing a small number of monosaccharides. Oligosaccharides can have

many functions including cell recognition and cell binding. Complex carbohydrates which have

three or more sugars are called polysaccharides (Szalay, 2015). These are composed of 10 to up

to several thousand monosaccharides arranged in chains. The most common monosaccharides

2016).

In the experiment, the physical and chemical properties of these carbonyl compounds and

carbohydrates are determined through their solubility in water and reactivity on certain reagents.

Specifically, oxidation with Tollens’ reagent, iodoform test, and 2,4-DNP test were conducted on

representative aldehydes, ketones, and carbohydrates. Also, hydrolysis was performed on di- and

polysaccharides as well as color reactions of carbohydrates with Mollisch reagent, Benedict’s

reagent, and formation of osazones with phenylhydrazine. These chemical tests were used to

classify carbonyl compounds and carbohydrates and their structures based on their solubility and

chemical reactivity.
II. Methodology
III. Results and Discussion

The properties of carbonyl compounds and carbohydrates were investigated in this

experiment. For each part, different compounds were used as test samples for their solubility and

reactivity in various reagents. Carbonyl compounds, which are composed of aldehydes and

ketones, and carbohydrates, which are classified into monosaccharides, disaccharides, and

polysaccharides were used in the experiment. The aldehydes used include acetaldehyde, which is

aliphatic, and benzaldehyde, an aromatic compound. For ketones, the representative compounds

were acetone, a symmetric aliphatic compound and cyclohexanone. For carbohydrates,

monosaccharides or one-sugar units are represented by glucose, fructose, and lactose;

disaccharides or two sugar units are represented by sucrose; while polysaccharides are

represented by starch and cellulose.

Table 1. Solubility behaviour of carbonyl compounds and carbohydrates

Sample Solubility behavior

benzaldehyde X

acetone X

glucose S

starch X

cellulose X

Legend: S – the sample is soluble or miscible in water

X – the sample is insoluble or immiscible in water

Table 1 shows the solubility of the samples in water as a test for homogeneity. It also

tests the strength of intermolecular forces between the sample and water as a solvengt.

Benzaldehyde and acetone were used in liquid form while glucose, starch, and cellulose were in
solid or powdered form. For benzaldehyde, a light yellow top layer was observed over the clear

bottom layer which indicates that it is not miscible with water. Acetone was observed to have a

smaller immiscible layer wherein both phases are clear. Glucose, which exists as a solid sample,

was dissolved in water, forming a clear solution. For starch, there is a presence of a small amount

of solids that settled at the bottom of the test tube, making it insoluble. Lastly, cellulose was

observed to have a jelly-like layer on top separated from the aqueous layer, which makes it

insoluble in water. In the experiment, only glucose was observed to have a complete

homogeneity with water since it is totally soluble in that solvent.

Carbonyl compounds contain a polar C=O double bond in its structure since the oxygen

atom pulls more electrons towards itself due to its higher electronegativity relative to carbon.

This makes the C atom partially positive since it is electron deficient while O atom is a partially

negative atom. Due to its polarity, carbonyl compounds with less than four carbon atoms are

freely soluble in water. This is because the intermolecular forces, in the form of hydrogen

bonding between the sample and water are relatively stronger which maximizes the interaction

between the two molecules. In hydrogen bonding, the O atom of the carbonyl compound is

attracted to the H atom of water due to their high difference in electronegativity. However, as the

carbon chain becomes longer, the nonpolar character of the molecule increases which makes it

insoluble in water (“The Carbonyl Group”, n.d.).

Carbohydrates, on the other hand, have varying degree of solubility based on their

structures. Monosaccharides and disaccharides contain several polar hydroxyl groups attached to

its carbon chain. Because of this, these compounds are freely soluble in water due to its

hydrogen-bonding on the hydroxyl groups. Polysaccharides, or multiple sugars liked in a linear

chain, are mostly insoluble because these compounds prefer partial crystallization (Whistler,
1973). Despite having hydrogen bonds present on the molecule, it is attracted to oxygen atoms in

the same molecule. This leads to a decrease in the interaction between the solute and water

molecules. In addition, as the number of OH groups increases, the strength of the polysaccharide

decreases (“Carbohydrates”, 2011).

For benzaldehyde, it was observed to be insoluble in water due to the presence of the

aromatic ring, which is considered as a large, nonpolar group which hinders it solubility. In 1 L

of water, only 6.95 g of benzaldehyde is soluble (NCBI, n.d.). Acetone, however, is ideally

soluble in water since it is only composed of two methyl groups attached to the carbonyl group

which accounts to its greater polar character as compared to longer-chained ketones, which

contradicts the results of the experiment. Quantitatively, its solubility is 1000 mg/mL at 25˚C

(NCBI, n.d.). Glucose, which is a monosaccharide, was also shown to be water-soluble, while

starch and cellulose are insoluble because they belong to the group of polysaccharides.

In this part of the experiment, only short-chained aldehydes and ketones as well as

monosaccharides were observed to be soluble in water which includes acetone and glucose. The

acetone sample, however, did not dissolve in water because the mixture was not mixed

completely; thus, an immiscible layer still exists in the sample. The concepts behind solubility

are based on the strength of intermolecular forces between the sample and the solvent.

Table 2. Hydrolysis of di- and polysaccharides

Sample Number of drops of NaOH used in titration

sucrose 36

starch 45

cellulose 39
 The results for the hydrolysis of disaccharides and polysaccharides are shown in Table 2.

In this process, the sample is broken down into simple sugars and the number of drops of sodium

hydroxide was determined in the titration until the solution turns pale pink due to the

phenolphthalein indicator. Based on the results, sucrose, a disaccharide, only took 36 drops of

NaOH until the pale pink color was observed which indicates that hydrolysis had been

completed. The polysaccharide starch came close with 39 drops of NaOH, and the sample with

greatest amount of titrant required was starch with 45 drops. It was observed that the

disaccharides are easily hydrolysable than polysaccharides since it needed a lesser amount of

base until hydrolysis is observed.

Hydrolysis is a reaction of polymers in which they are broken down into monomers with

a water molecule. In this reaction, the polymer is broken into two components wherein one part

gains a hydrogen ion and a hydroxyl group is added on the other. One example of this reaction is

the hydrolysis of disaccharides and polysaccharides. It is usually done at a higher temperature,

ranging from 100-180˚C to ensure rapid dissolution of the molecules (Kaye et. al., 2014). Figure

1 shows a hydrolysis reaction which shows that maltose is separated into two glucose molecules

through hydrolysis (Boundless, n.d.).

Figure 1. The structure of maltose (left) is shown in the hydrolysis reaction to form two

glucose molecules.
 When sucrose is hydrolyzed, it is broken down into equal amounts of glucose and

fructose. A water molecule breaks the acetal bond with the help of an acid catalyst and it

dissociates into H+ and OH- ions. Then, hydrogen is added to the oxygen to form glucose while

OH is added to carbon to form fructose (Ophardt, 2003). Starch, on the other hand, can also be

hydrolyzed with an acid (e.g. HCl) and heat to form glucose molecules. Heat is required so that

the acetal bonds in starch are weakened. Also, the hydrolysis for starch occurs at a slower rate

because it contains many bonds that should be broken (“Hydrolysis of Starch”, n.d.). For

cellulose, the β-1,4-glycosidic bonds are broken to form glucose molecules, which is the same as

for starch. The difference between the two is that the bonds connecting glucose molecules are

strong enough that the hydrolysis occurs at an even slower rate (Huang and Fu, 2013).

Based on the results, sucrose only required the least amount of base for neutralization

because its hydrolysis reaction is the fastest among the samples. It is because only one bond is

broken in the disaccharide. For starch, several bonds should be broken thus it should require

more drops of NaOH. Lastly, for cellulose, the strength of the bonds are greater than that of

starch; therefore it requires the most amount of base for neutralization. In general, the rate of the

hydrolysis of reaction is based on the number of bonds that connect individual monomers and the

strength of these bonds.

Table 3. Reactivity of carbonyl compounds with Tollens’ reagent

Sample Solubility behavior

acetaldehyde R

acetone X

Legend: R – the sample reacted with Tollens’ reagent

X – the sample did not react with Tollens’ reagent

different reagents. Table 3 shows the reactivity samples with Tollens’ reagent which is also

known as ammoniacal silver nitrate. A positive result is indicated by the presence of a silver

mirror on the walls of the test tube. From the results presented above, acetaldehyde gave a

positive result due to light-grey coating that covered the liquid mixture which resembled a silver

mirror. However, white particles were present on the test tube due to the impurities present both

in the sample and in the reagent used. For acetone, however, there was no silver mirror observed

which led to a negative result in the experiment. A light brown, clear solution was just observed

which can also be traced from the impurities in the sample. In the experiment, it was shown that

aldehydes are reactive with Tollens’ reagent while ketones are not.

Tollens’ test is used in the laboratory for the presence of aldehydes in a sample and to

differentiate it from ketones. The reagent used is a colorless, basic, aqueous solution of

ammoniacal silver nitrate, or silver ions coordinated to ammonia (Ag(NH3)2+). In this reaction,

the aldehyde is oxidized due to the hydrogen atom attached to the carbonyl group to form either

carboxylic acids in acidic conditions or carboxylates in basic conditions. Ketones, however, are

not oxidizable due to the absence of the oxidizable hydrogen atom. The chemical reaction of

aldehydes and the silver ions in the reagent is denoted by (Gunawendara, 2016; Clark, 2004).

In the experiment, acetaldehyde reacted with Tollens’ reagent to form a silver mirror

while acetone did not. However, the white particles are due to the impurities in the reagent which

may affect its freshness. Also, the test tube must be clean properly so that silver will not

precipitate due to the impurities present which may act as nuclei for precipitation (Heckathorn,
2016). Thus, Tollens’ reagent was proven to be reactive with aldehydes to form a silver mirror

on walls of the test tube wile ketones are not reactive to this reagent.

Table 4. Reactivity of carbonyl compounds in the iodoform test

Sample Reactivity

acetone R

cyclohexanone X

acetaldehyde X

Legend: R – the sample reacted to produce iodoform

X – the sample did not react to produce iodoform

In Table 4, the results for the formation of iodoform using these samples is presented. A

yellow precipitate should be observed in order to yield a positive result. Based on the results,

acetone changed its color to light yellow after the titration with NaOH and heating; therefore, a

positive result was given to acetone. For cyclohexanone, its color changed to light orange after

heating and the solution became unclear. However, the precipitate cannot be distinguished in the

sample, thus the iodoform formation did not occur. For acetaldehyde, however, the solution

turned colorless after heating and there was no precipitate; therefore, it yielded a negative result.

From the experiment, ketones (acetone and cyclohexanone) can produce iodoform in this test

while aldehydes cannot.

Iodoform test is used to detect the presence of acetaldehyde (ethanal) and methyl ketone

in a sample. The formation of iodoform (CHI3), a yellow solid with an odor which resembles

antiseptic, is possible when the structure of the compound contains methyl attached to a carbonyl

group (One Part of Chemistry, n.d.). The reaction follows the mechanism of a nucleophillic

substitution, in which excess base and iodine are used to halogenate and cleave the methyl
ketone or ethanal. First, three atoms of iodine substitute the hydrogens in the methyl group.

Then, the OH group attacks the carbonyl carbon and CI3- acts as the leaving group. Lastly, the

carboxylic acid donates a proton to the carbanion and iodoform is formed (McMurry, 2008). The

overall equation for the iodoform reaction is described by (Clark, 2004)

In the experiment, acetone was proven to have a positive result due to the light yellow

coloration of the mixture. Its structure contains two methyl groups attached to either side of the

carbon. Cyclohexanone, on the other hand, did not react to produce iodoform because it is a

cyclic ketone that does not contain any methyl groups attached to the carbonyl group. Lastly,

acetaldehyde should ideally give a positive result in this test; however, the sample turned

colorless which indicated a negative result. The colorless solution was observed after the sample

was heated in a water bath. Possible errors that may cause this false result include overrun of

base, insufficient shaking of the tube during titration, and a higher amount of heat applied to the

sample which made the iodoform precipitate dissolved in water. In general, acetaldehyde and

ketones containing a methyl group can only react with iodine and NaOH to produce iodoform.

From the samples used in the experiment, acetone was proven to give a positive result but

acetaldehyde was not due to some experimental errors.

Sample Solubility behavior Color of precipitate

acetone PR orange

acetaldehyde PR light orange

glucose X N/A

fructose X N/A

cyclohexanone R yellow

benzaldehyde R light orange

Legend: R – the sample is reactive with 2,4-DNP

PR – the sample is partially reactive with 2,4-DNP

X – the sample is unreactive with 2,4-DNP

Table 5 shows the reaction progress of carbonyl compounds and carbohydrates with 2,4-

dinitrophenylhydrazine (DNP). A positive result occurs if a solid precipitate forms in the

solution, while the sample is considered partially reactive when the sample is not completely

solidified. On the other hand, negative result for this reaction happens when the solution remains

in its liquid form. From the results, acetone and acetaldehyde were observed to have a powdery

form and they were not completely solidified, making them partially reactive with 2,4-DNP. The

difference between the two samples is based on their color, wherein acetaldehyde has a lighter

orange color than acetone. Glucose and fructose, however, are not reactive to the reagent because

two liquid immiscible phases were formed, showing no interaction between the two species.

Lastly, cyclohexanone and benzaldehyde yielded a positive result since they were completely

solidified with the reagent. The difference between the two is also based on their color;

cyclohexanone was observed to be yellow while benzaldehyde turned orange. To summarize

or partially reactive with the reagent.

The compound 2,4-dinitrophenylhydrazine (shortened as 2,4-DNP, also known as

Brady’s reagent) is used as a precipitating agent for aldehydes and ketones due to the presence of

a carbonyl group in its structure. It gives an orange-yellow precipitate to the samples in a form of

a 2,4-DNP derivative which has a characteristic melting point. These derivatives are solid in

room temperature because they have a high molecular weight as well as high polarity. However,

esters, amides, and carboxylic acids do not form a precipitate with the reagent due to the

presence of another oxygen atom attached to the carbonyl group which may form resonance

structures which stabilizes the molecule and makes it more resistant to this reaction (The Student

Room, n.d.).

Also, the structure of the samples is based on the color of the precipitate. A conjugated

carbonyl group produces a reddish-orange product, while a unconjugated carbonyl group yields a

yellow product. Conjugated compounds are those which have two double bonds separated by a

single bond, such as benzaldehyde. Also, larger molecules such as cyclohexanone and

benzaldehyde undergo a faster and a more complete reaction because they can form a more

stable carbocation intermediate through inductive effect and electron delocalization. The net

reaction of carbonyl groups with 2,4-DNP is defined by (Online Lab Manual Home, n.d.).

-
 In the experiment, acetone and acetaldehyde were shown to react partially with 2,4-DNP

since they have smaller molecules relative to other samples. Because of their size, they have a

less stable carbocation intermediate since there are lesser carbons which can donate electron

density. Both samples yielded an orange precipitate although they are non-conjugated. Glucose

and fructose, however, are not reactive with 2,4-DNP since carbohydrates can either attain a

cyclic or straight-chain form at equilibrium and the reagent can only interact with straight-chain

sugars since they contain aldehyde groups. Lastly, benzaldehyde and cyclohexanone are

completely reactive due to their large structures. Benzaldehyde, which is conjugated, produced

an orange color while the precipitate of cyclohexanone, a non-conjugated ketone, is colored

yellow. To sum it up, 2,4-DNP reactions are used to test the presence of aldehydes and ketones,

however, carbohydrates do not give a positive result due to its conversion to its cyclic form.

Carbonyl compounds with larger groups as substituents are more reactive than smaller molecules

due to the stability of its intermediate.

Table 6. Results of the color reaction of carbohydrates with Molisch test

Sample Interface color

cyclohexanone yellow

glucose pink

starch pink-purple

sucrose dark brown

For Part D of the experiment, the different color reactions of carbohydrates were

observed in order to distinguish each one from the other. Table 6 shows the color of the interface

of each sample using Molisch reagent. From the results, cyclohexanone yielded a yellow

interface which is found at the middle of the solution. Also, a large yellow immiscible layer was
observed on top of the clear liquid. For glucose, a pink interface was observed and a few bubbles

formed on top of the solution. For starch, a faded pink-purple interface and an immiscible layer

was observed in the sample. Lastly, sucrose, the interface observed has a dark brown color and

the sample is also immiscible. In summary, each sample produced a distinct color of interface in

this test.

Molisch test is used to determine and identify the carbohydrates in the sample. It is

positive for all types of carbohydrates both in free and combined forms. In performing this test,

the sample is first treated with acid (e.g. HCl) to hydrolyze polysaccharides into

monosaccharides. As water is removed, furfural is produced and then condensed with alpha

nephthol in Molisch’s reagent to form a reddish-violet ring at the interface of the liquid (All

Medical Stuff, 2016). The reaction of the formation of the ring is denoted by (The Wall of

Biochemistry, n.d.).

Based on the observations, cyclohexanone did not exhibit a reddish-violet precipitate

since it is not a carbohydrate; instead, a faded yellow interface was observed. For glucose, a pink

interface was seen on the solution. Also, it was deduced that glucose will have the fastest

reaction rate since it is a monosaccharide and does not hydrolyze. For starch, a faded pink-purple

interface was observed due to the slower rate since it has more bonds to be broken in order for it
to be converted into glucose monomers. Lastly, sucrose yielded a dark brown color in this test

which indicates that it also gives a positive result. It also undergoes hydrolysis which makes it

react slower compared to glucose but faster than starch (“The Molisch Test”, n.d.). In summary,

all carbohydrates produced a positive result with Molisch test and the rate of the reaction

depends on the extent of hydrolysis, i.e., the smaller the molecule, the faster its reaction rate.

Table 7. Reactivity of carbohydrates with Benedict’s test

Sample Reactivity Color after heating

glucose R brown/dark yellow

fructose R brown/dark yellow

sucrose X blue green

lactose R orange-brown

hydrolysates

starch R blue-grey

cellulose R blue

sucrose R dark brown

Legend: R – the sample reacted after heating with Benedict’s reagent

X – the sample did not react after heating with Benedict’s reagent

Table 7 shows the reactivity and the color change of the samples after heating with

Benedict’s reagent. A reaction is observed if there is a color change before and after it was

heated in a boiling water bath. For the carbohydrates the initial color was blue/blue green, while

for hydrolysates, it was initially purple top layer and blue bottom layer. Based on the results for

carbohydrates, glucose, fructose, and lactose was observed to have a color change into brown or

orange brown. This indicates that there is a reaction that occurred with the Benedict’s reagent.
However, the solution remained blue green for sucrose which means that it is not reactive with

the reagent. For hydrolysates, all the samples reacted with the reagent since each of them were

observed to have different colors as compared to the initial. Thus, only sucrose in its

carbohydrate form is unreactive with Benedict’s reagent while the rest of the samples underwent

a chemical reaction.

Benedict’s test is a chemical analysis used to detect reducing sugars, or those containing

an aldehyde functional group in its open chain form. Also, sugars with a ketone group can also

be converted into aldehydes when it is an open chain. Reducing sugars include monosaccharides

(glucose, fructose, and galactose) and some disaccharides (lactose and maltose). However,

sucrose, which is also a disaccharide, is a non reducing sugar because it does not contain an

aldehyde group in its structure. Benedict’s reagent is used in this reaction which is composed of

copper (II) sulphate, sodium carbonate, and sodium citrate.

This test can either be qualitative or quantitative in nature. A qualitative Benedict’s test

involves the detection of a color change from its original blue color to green to yellow to orange

to brick red. At the same time, this can also be semi-quantitative since its color is related to the

concentration of reducing sugars in the solution. The order of the colors of solution in increasing

concentration is blue<green<yellow<orange<red. The reaction with Benedict’s reagent occurs

when an aldehyde group reduces Cu2+ ions into Cu+ in the form of copper oxide (Cu2O), a brick

red precipitate (Brilliant Biology Student, n.d.). The net equation for this reaction is (“Benedict’s

Test”, n.d.)
 In the experiment, a brown precipitate was observed for glucose, fructose, and lactose

due to the formation of copper oxide precipitate since these monosaccharides have aldehyde

groups in its open chain form which can be exposed in the presence of heat. However, sucrose

did not react with the reagent since it does not contain an aldehyde group in its structure. For the

hydrolysates, the blue-grey color of starch hydrolysate indicates that there is a low concentration

of reducing sugars brought by incomplete hydrolysis. Cellulose hydrolysate was also observed to

be blue which means that it also has few reducing sugars. However, sucrose hydrolysate yielded

a brown color due to the presence of glucose and fructose which are products of hydrolysis and

are reducing sugars. For this part of the experiment, the reducing sugars detected using

Benedict’s reagent are found in glucose, fructose, lactose, and sucrose hydrolysates.

Table 8. Results of the osazone formation based on the time of precipitation

Sample Time of precipitation (mm:ss)

glucose 7:19

fructose 3:43

starch 30:47

lactose no change

Table 8 shows the reactivity of the carbohydrates with phenylhydrazine-

HCl/NaCH3COOH based on the rate of osazone formation. This formation can be observed in

the form yellow precipitate which is produced as it is heated in a boiling water bath. Based on

the results, fructose has the highest reaction rate since it only took 3 minutes and 43 seconds until

a yellow precipitate is formed. Then, glucose formed a precipitate with the reagent after about 7

minutes of immersion. For starch, it took about 30 minutes for it to form a precipitate and this is

possibly due to its polysaccharide character unlike glucose and fructose. However, lactose,
which is a monosaccharide, did not form an osazone while it is heated but instead it was formed

when it is already cooled. In this case, the time of precipitation was not recorded since it had

stopped after lactose was removed from the water bath. To sum it up, the decreasing order in

which osazone formation can react rapidly is fructose>glucose>starch>lactose.

Osazone test is used to identify sugars based on their reaction with phenyl hydrazine.

Osazones are carbohydrates which are derived from different part of sugars which are usually in

crystalline form. These crystals can be observed using a microscope in order to see their various

shapes (e.g. petals, needles,rhombic). Only reducing sugars can form osazones with phenyl

hydrazine reagent; thus, sucrose do not form osazone crystals. The reaction involved in the

formation of osazone is an alpha-carbon oxidation to produce bis-phenylhydrazone. For D-

fructose and D-glucose, they produce the same osazones in which their differences are masked

with the crystals are formed (Chhabra, 2015). Thus, needle-shaped crystals can be observed in

the solution as osazone. The formation of similar osazones of these carbohydrates are shown by

(Ziegler, 2016)
 For glucose, it took about 7 minutes until osazone formation to occur. Monosaccharides

have needle-shaped crystals when they are seen under the microscope, which shows that the

position of carbons 1 and 2 does not affect crystal formation. Ideally for glucose, osazone is

formed in about 4-5 minutes, and the experimental time is close to these values. Fructose, which

is also a monosaccharide, has the same needle-shaped crystals as glucose and the ideal time for it

to form osazone is 2 minutes which is also close to the data obtained (Caton, 2011). Starch,

which is a non-reducing polysaccharide, cannot form osazone without hydrolysis; thus, it took

about 30 minutes for crystals to appear. A special case happens with lactose since its osazone

formed is soluble in hot water; therefore, cooling is needed in order to see the osazone crystals

from lactose (Ashok, n.d.). For this test which applies to carbohydrates, its rate of formation of

osazone is determined based on the identity of the sugar. Fructose is the first to form crystals,

followed by glucose and then starch, while lactose crystals are formed at lower temperatures due

to its solubility in hot water.

A. Conclusion

B. Recommendation
V. References and Appendices

A. References

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ps/chm/100/dgodambe/thedisk/carbo/bened/benedict.htm

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from http://www.chemguide.co.uk/organicprops/carbonyls/iodoform.html
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Huang, Y.B., Fu, Y. (2013). Hydrolysis of cellulose to glucose by solid acid catalysts. Green

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Hunt, I. (n.d.). The haloform reaction. Retrieved from

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starch.html

Identification of an Unknown – Alcohols, Aldehydes, and Ketones (n.d.). Retrieved from

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National Center for Biotechnology Information (n.d.). Acetone. PubChem Compound Database.

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Database. Retrieved from https://pubchem.ncbi.nlm.nih.gov/compound/240

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 B. Appendices

1. Raw Data

Table 1. Observations for the solubility behaviour

Sample Observations

benzaldehyde immiscible, light yellow bottom layer

acetone immiscible, clear

glucose clear, solid dissolved

starch clear, insoluble, precipitate settled at the bottom

cellulose clear bottom layer, insoluble, jelly-like white top layer

Table 2. Results for the hydrolysis of Di- and Polysaccharaides

Sample Number of drops of NaOH used in titration

sucrose 36

starch 45

cellulose 39

Table 3. Observations for the reaction with Tollens’ reagent

Sample Observations

before heating after heating

acetaldehyde colorless, clear, immiscible silver mirror formed, unclear, white

particles on mirror

acetone colorless, clear, immiscible light brown, clear, immiscible

Sample Observations

after adding I2/KI after adding NaOH after heating

acetone colorless, clear, light yellow, clear light yellow, clear

miscible

cyclohexanone orange, clear, large light yellow, clear orange, unclear,

immiscible layer miscible

acetaldehyde orange, clear, miscible light yellow, clear colorless, clear,

immiscible

Table 5. Observations from the reaction with 2, 4-DNP

Sample Observations

acetone liquid, unclear, miscible, powdery, orange

acetaldehyde not completely solidified, light orange, soluble

glucose clear, orange, immiscible

fructose clear, orange, immiscible

cyclohexanone solidified, yellow

benzaldehyde solidified, light orange

Table 6. Observations from the Molisch test

Sample Observations

cyclohexanone yellow interface, colorless, clear, large yellow immiscible layer

glucose pink interface, colorless, clear, bubbles form on top

sucrose dark brown interface, colorless, immiscible

Table 7. Observations from Benedict’s test

Sample Observations

before heating after heating

glucose blue brown/dark yellow, dark particles formed

fructose blue brown/dark yellow, dark particles formed

sucrose blue blue green, slightly clear

lactose blue orange-brown, unclear, dark particles at bottom

hydrolysates

starch violet top, blue bottom blue-grey, brown parts

cellulose violet top, blue bottom blue

sucrose violet top, blue bottom dark brown, yellow

Table 8. Results and observations from the osazone formation

Sample Observations Time of immersion Time of precipitation

(mm:ss) (mm:ss)

glucose yellow, unclear, yellow precipitate 0:00 7:19

clump, bubbles form on top

fructose yellow, unclear, yellow precipitate 0:00 3:43

clump

sucrose yellow, unclear, yellow precipitate 0:00 30:47

lactose yellow, unclear, yellow precipitate 0:00 no change

formed after it was heated

2. Photos