SIC3023

PRACTICAL OF ORGANIC CHEMISTRY III

LAB REPORT EXPERIMENT 2: ANALYSIS OF A BINARY MIXTURE

PREPARED FOR: ASSOCIATE PROF. DR. LOW YUN YEE

NAME SUMAYYAH BINTI LOKMAN

MATRIC NO. 22003285/1

SESSION 2024/2025

SEMESTER 1

OCCURANCE 1
1.0 TITLE

Analysis of a binary mixture

2.0 OBJECTIVES
1. To separate the two compounds in the unknown binary mixture
2. To identify the two compounds in the binary mixture using a combination of classical
qualitative analysis and spectroscopy.
3. To measure the melting point of the two compounds in the unknown binary mixture.

3.0 INTRODUCTION

A combination made up of two different molecular components is called a binary mixture. This
experiment's primary goals are to identify the unknown substances and separate a binary
mixture. The two components of a binary mixture can be separated using a variety of methods.
For instance, chromatography, evaporation, distillation, neutralisation, and filtering (Magen,
2020). The many physical or chemical characteristics of the two components, such as their
density, solubility, melting and boiling points, and chemical reactivity, serve as the foundation
for all separation methods (Harvey, 2021).

The binary mixture will contain either acidic compound + neutral compound or basic
compound + neutral compound. Therefore, it was necessary to identify the type of binary
combination before separating the two components. Following the isolation procedure, a
number of chemical tests will be conducted as part of a qualitative study to identify the two
components. The structures of atoms and molecules may be studied with the use of
spectroscopy. The two unknown components will be identified using spectroscopic techniques,
which essentially involve the absorption of certain electromagnetic radiation (Andreas, 2010).
This experiment will employ three different forms of spectroscopies: 1H NMR, 13C NMR, and
IR.
4.0 METHODOLOGY
4.1 SEPARATION AND IDENTIFICATION OF TYPE OF BINARY
MIXTURE
1. Three different test tube are added with distilled water, 5% hydrochloric acid (HCl) and
5% sodium hydroxide (NaOH).
2. A small amount of binary mixture is added to each of the test tubes. The solubility of
the compound is observed. If the compound does not dissolve immediately, put the test
tube in a water bath and heat it.
3. After identifying that the binary mixture is an acidic + neutral compound, proceed to
separation of compounds.
4. The compound is poured in a conical flask containing 5% NaOH and continuous stirring
is applied for 10 minutes.
5. Then the rest of the steps are as follows:

Figure 1: flow chart of separation and purification of the mixture containing

acidic and neutral components.
4.2 NEUTRAL COMPOUND
4.2.1 LASSAIGNE’S TEST
1. 0.01g of compound is placed into a Pyrex tube containing 0.05g of freshly cut
sodium metal.
2. The tube is heated strongly using Bunsen burner until the bottom of the tube is
glowing red for 5 minutes.
3. The tube is then plunged into an evaporating dish containing distilled water and
covered using wire gauze.
4. The tube is crushed and the mixture is heated until boiling.
5. The mixture is then filtered gravitationally using fluted filter paper.
6. If coloured filtrate is obtained then the whole process is repeated again as the
combustion is incomplete.

Test for nitrogen

1. 0.5 Ml of the filtrate is added to a tube containing 0.1-0.2 g of powdered iron(ii)
sulphate crystals.
2. The mixture is heated until boiling and dilute sulphuric acid is added without
cooling the mixture.
3. A Prussian blue precipitate indicates the presence of nitrogen.

Test for sulphur

1. ~0.5 mL of the filtrate is acidified with dilute acetic acid.

2. A few drops of 1% lead acetate solution is added. A black precipitate indicates
the presence of sulphur.

Test for halogens (if nitrogen and or sulphur present)

1. ~ 0.5 mL of the filtrate is acidified with dilute nitric acid and concentrated to
half of its original volume to expel any hydrogen cyanide or hydrogen sulphide
that might be present in the mixture.
2. The mixture is diluted with an equal volume of distilled water.
3. 1-2 drops 5% of aqueous silver nitrate solution is added to 2-3 mL of the fusion
solution. An immediate heavy precipitation indicates the presence of chlorine,
bromine, or iodine.
 Test for halogens (if nitrogen and sulphur are absent)

1. A portion of the filtrate is acidified with dilute nitric acid and an excess of 5%
silver nitrate solution is added. Precipitation indicates the presence of chloride,
bromide or iodide. Silver chloride precipitate is white, silver bromide precipitate
is pale yellow and silver iodide precipitate is yellow.
2. The solvent is removed and the precipitate is treated with dilute aqueous
ammonia solution. 2 mL 5% ammonium hydroxide is added to the precipitate.
Silver chloride is soluble in ammonium hydroxide, silver bromide is slightly
soluble and silver iodide is insoluble in ammonium hydroxide solution.

4.2.2 BRADY TEST

1. 0.05g of the compound was dissolved in 2mL 95% ethanol.
2. In a test tube containing 2,4-dinitrophenylhydrazine reagent, around 3 drops of the
dissolved compound was added.
3. The tube is shaken well and the observations were recorded.

4.2.3 SODIUM BISULPHITE SOLUTION TEST

1. The alcoholic sodium bisulphite solution is prepared by adding 1 mL ethanol to 4
mL aqueous solution of sodium bisulphite. The reagent is filtered.
2. Around 0.2 mL of the compound is added in a test tube containing 1 mL alcoholic
sodium bisulphite solution.
3. Plug the test tube and shake thoroughly.
4. The observation is recorded.

4.2.4 TOLLENS’ TEST

1. 2-3 drops of the compound are added to a test tube containing tollens’ reagent.
2. The tube is shaken. The presence if silver mirror/precipitate prove the presence of
aldehyde group.
3. If there is no precipitate after 10 minutes, warm the mixture in water bath at 30℃
for 5-10 minutes.
4.3 ACIDIC COMPOUND
4.3.1 LASSAIGNE’S TEST
1. 0.01g of compound is placed into a Pyrex tube containing 0.05g of freshly cut
sodium metal.
2. The tube is heated strongly using Bunsen burner until the bottom of the tube is
glowing red for 5 minutes.
3. The tube is then plunged into an evaporating dish containing distilled water and
covered using wire gauze.
4. The tube is crushed and the mixture is heated until boiling.
5. The mixture is then filtered gravitationally using fluted filter paper.
6. If coloured filtrate is obtained then the whole process is repeated again as the
combustion is incomplete.

Test for nitrogen

4. 0.5 Ml of the filtrate is added to a tube containing 0.1-0.2 g of powdered iron(ii)
sulphate crystals.
5. The mixture is heated until boiling and dilute sulphuric acid is added without
cooling the mixture.
6. A Prussian blue precipitate indicates the presence of nitrogen.

Test for sulphur

3. ~0.5 mL of the filtrate is acidified with dilute acetic acid.

4. A few drops of 1% lead acetate solution is added. A black precipitate indicates
the presence of sulphur.

Test for halogens (if nitrogen and or sulphur present)

4. ~ 0.5 mL of the filtrate is acidified with dilute nitric acid and concentrated to
half of its original volume to expel any hydrogen cyanide or hydrogen sulphide
that might be present in the mixture.
5. The mixture is diluted with an equal volume of distilled water.
6. 1-2 drops 5% of aqueous silver nitrate solution is added to 2-3 mL of the fusion
solution. An immediate heavy precipitation indicates the presence of chlorine,
bromine, or iodine.
 Test for halogens (if nitrogen and sulphur are absent)

3. A portion of the filtrate is acidified with dilute nitric acid and an excess of 5%
silver nitrate solution is added. Precipitation indicates the presence of chloride,
bromide or iodide. Silver chloride precipitate is white, silver bromide precipitate
is pale yellow and silver iodide precipitate is yellow.
4. The solvent is removed and the precipitate is treated with dilute aqueous
ammonia solution. 2 mL 5% ammonium hydroxide is added to the precipitate.
Silver chloride is soluble in ammonium hydroxide, silver bromide is slightly
soluble and silver iodide is insoluble in ammonium hydroxide solution.

4.3.2 SODIUM BICARBONATE (TEST FOR CARBOXYLIC ACID)

1. 1 mL of 5% NaHCO3 is poured in a watch glass.
2. 0.1g of the compound is added.
3. The observation is recorded.

4.3.3 ESTERIFICATION
1. Add around 1 mL of the compound and 5 drops of concentrated sulphuric acid to
2mL of ethanol in a test tube.
2. The mixture is warmed for 2 minutes and poured into aqueous sodium carbonate
solution in an evaporating dish after cooling. The mixture is smelled immediately.
3. Record the smell. An acid would yield a sweet, fruity smell of an ester. (However,
acids of high molecular weight often give almost odorless esters)
5.0 RESULTS
5.1 SEPARATION AND IDENTIFICATION OF TYPE OF BINARY
MIXTURE

Unknown number: 2
Physical state binary mixture: solid + solid
 Reaction with Solubility
Water Insoluble
HCl Insoluble
NaOH Soluble
NaHCO3 Soluble
Table 1: Solubility of binary mixture

As the binary mixture is soluble in NaOH, the binary mixture is acidic + neutral
compound.

5.2 ANALYSIS OF NEUTRAL COMPOUND

Figure 2: Neutral compound after separation

Melting point of the compound= 47-49℃

Lassaigne’s test result:

Cl Br I N S
Absent Absent Absent Absent Absent

Solubility test:

Water 5% NaOH 5% HCl 5% NaHCO3

Insoluble Insoluble Insoluble Insoluble
Functional group test:

Reagent/test Results Conclusion

Brady Presence of carbonyl
groups (aldehyde or
ketone)

Orange precipitate formed

Sodium bisulphite No precipitate No unhindered carbonyl
solution group (bulky)
Tollens’ No silver mirror/ No aldehyde group
precipitate formed present

IR spectrum:

Figure 3: IR spectrum of neutral compound

 IR interpretation of neutral compound:

Wavenumber/ cm-1 Functional group

3056.65 C-H stretch aromatic
1649.23 C=O stretch carbonyl
1593.63, 1575.36 C=C stretch aromatic

Figure 4: NMR spectrum of neutral compound

NMR interpretation:

Proton Chemical shift/ppm Integration No. of proton Structure of compound

Ha 7.454-7.491 2 2
Hb 7.558-7.598 4 4
Hc 7.784-7.804 4 4

Due to the symmetry of the molecule, the proton environment present is only three
which is a, b, and c.
 5.3 ANALYSIS OF ACIDIC COMPOUND

Figure 5: Acidic compound after separation

Melting point of the compound= 142-144℃

Lassaigne’s test result:

Cl Br I N S
Present Absent Absent Absent Absent

Solubility test:

Water 5% NaOH 5% HCl 5% NaHCO3

insoluble Soluble Insoluble Soluble

Functional group test:

Reagent/test Results Conclusion

Sodium bicarbonate (test Bubble formed (CO2 gas) Carboxylic acid present
for carboxylic acid)
Esterification Fruity smell Carboxylic acid present
IR spectrum:

IR spectrum interpretation of acidic compound:

Wavenumber/ cm-1 Functional group

2555.07-2880.40 O-H stretch carboxylic acid
1681.69 C=O stretch carboxylic acid
3391.28 C-H stretch aromatic
 NMR spectrum:

NMR interpretation:

Proton Chemical Integration No. of proton Structure of compound

shift/ppm
Ha 7.250 0.93 1
He
Hb, Hc 7.448-7.501 1.99 2
Hd 7.999-8.020 1.00 1
Ha

Hb Hd
Hc

Exchangeable proton OH is not shown on nmr spectrum (~ 10-13 ppm).

6.0 DISCUSSION
6.1 SEPARATION AND IDENTIFICATION OF TYPE OF BINARY
MIXTURE

A simple identification test is done by dissolving the unknown binary compound in

water, HCl, NaOH, and NaHCO3. As the unknown compound dissolved completely in
5% NaOH, a deduction was made which is the compound is the mixture of acidic and
neutral compound as acidic and basic compound react with each other to undergo
neutralisation process.

6.2 NEUTRAL COMPOUND

Lassaigne’s test is commonly done to detect the presence of nitrogen, sulphur, and halogens
such as chlorine, bromine and iodine. In a fusion tube with sodium metal present, the organic
substance for which the test is to be performed is heated. The sodium metal transforms the
compound's elements into sodium fusion extract, an ionic form. In order to look for any
noticeable changes that might suggest the existence of a certain element in the molecule, this
extract is subsequently subjected to further treatment with particular reagents. From the
lassaigne’s test done on the compound, all of the elements (nitrogen, sulphur, and halogens)
are absent in neutral compound. Additionally, the compound is not soluble in water, HCl,
NaOH, and NaHCO3.

From the functional group test, it is found that the compound contains carbonyl group,
specifically ketone. To confirm the presence of carbonyl group, we look at the IR spectrum of
the compound. The presence of carbonyl group is proved with C=O stretch carbonyl peak at
1649.23 cm-1.

The melting point of the compound is 47-49℃. After the functional group test is carried out
and the melting point of the compound is taken, the possible compound that matches both of
the criteria is benzophenone which contains ketone group and theoretical melting point of 47-
49℃.
 Figure 6: structure of benzophenone

6.3 ACIDIC COMPOUND

From the lassaigne’s test conducted for acidic compound, it if found that only chlorine is
present. this is due to the white precipitate formed when the compound is acidified with nitric
acid and reacted with excess 5% silver nitrate solution. The unknown acidic compound is
soluble in NaOH and NaHCO3 and insoluble in water and HCl.

From the functional group tests conducted, it is found that carboxylic acid is present in the
compound. When the compound is reacted with sodium bicarbonate, bubbles (CO2 gas) are
formed. It can be explained with equation below:

RCOOH + NaHCO3 → RCOONa + H2 O + CO2

By doing another functional group test which is the esterification test, it strengthens the
possibility of having carboxylic acid group in the compound as fruity smell is produced when
the compound reacted with ethanol. However, the smell is mild and not that strong due to the
chlorine present in the same compound.

To prove the presence of carboxylic acid, IR spectrum shows the presence of C=O stretch of
carboxylic acid at 1681.69 cm-1 and O-H stretch of carboxylic acid at 2555.07-2880.40 cm-1.

The melting point of the acidic compound is 142-144℃. The possible compound that matches
the melting point, the functional group present, and NMR is o-chlorobenzoic acid or 2-
chlorobenzoic acid.
 Figure 7: Structure of o-chlorobenzoic acid

7.0 CONCLUSION

After separating the binary unknown mixture, observing the physical properties, carrying
out lassaigne’s test and functional group test, interpreting IR and NMR spectrum, and
taking the melting point, the neutral and acidic compound is found to be benzophenone and
o-chlorobenzoic acid respectively. The melting point of benzophenone is 47-49℃ while
the melting point for o-chlorobenzoic acid is 142-144℃.
 8.0 REFERENCES

Department of Chemistry, Faculty of Science, Universiti Malaya. (2023). SIC3023 Organic Chemistry
III. Universiti Malaya

GeeksforGeeks. (2024, April 5). Lassaigne Test. GeeksforGeeks.

https://www.geeksforgeeks.org/lassaigne-test/

Libretexts. (2020c, November 3). Infrared Spectroscopy Absorption Table. Chemistry LibreTexts.
https://chem.libretexts.org/Ancillary_Materials/Reference/Reference_Tables/Spectroscopic_
Reference_Tables/Infrared_Spectroscopy_Absorption_Table