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EXPERIMENT I

SOLUBILITY OF ORGANIC COMPOUNDS

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ABSTRACT

This experiment aim at determining the solubility of organic compounds such as phenol, Naphthalene,
1-propanol,2 –butanol, cyclohexanol, Benzyl alcolol, aniline and Benzamide in water, cyclohexene, Ethyl
acetate, Toluene, dilute HCl, NaOH and NaHCO3 .

A sample of each organic compound was taken into a test tube with addition of solvent. Some of organic
compound appeared to dissolve in solvent when were shaken thoroughly at room temperature and
other at warm condition (heated in steam bath) while other appeared not to dissolve at all due to
polarity and intermolecular force existing between them. Compounds that are insoluble in water can
become soluble in aqueous environment if they form an ionic species when treated with acid or base.
This is because the ionic form is more polar. From general rule that like dissolve like, polar solute
dissolved in polar solvent and non-polar solute in non-polar solvent.

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INTRODUCTION:

The purpose of this experiment is to determine the solubility characteristics of some simple organic
compounds. Predicting the solubility of organic compounds is a useful skill. For example it can be useful
when trying to purify (e.g recrystallization: picking a suitable solvent) solute from a multi-compounds
reaction mixture (e.g via extraction) or when extracting molecules from a natural source such as plants.
This knowledge is also important when performing reaction to synthesize molecules, usually reagents
and starting materials are mixed together in solution.

Solubility is really controlled by intermolecular forces. General rule is “like dissolve like” and it is based
on the polarity of the system i.e. polar molecules dissolve in polar solvents and non-polar-molecules in
non-polar solvents. The polarity of organic molecules is determined by the polar bonds due to the
presence of electronegative atoms in polar bonds due to the presence of electronegative atoms in polar
functional groups such as amines (-NH2) and alcohols (-OH).

We are going to determine what compounds can be dissolved in each other or are miscible in each other
in a qualitative manner. As a result we should be able to determine which compounds have similar
characteristics with regard to solubility.

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THEORETICAL PRINCIPLES

When two substances are mixed together they may or may not dissolve in each other depending on a
variety of characteristics and properties associated with each substance. If they dissolve in each other,
they are considered to be soluble or miscible with each other. For example, table sugar can be dissolved
in water and alcohol is miscible in water. When sugar or alcohol is dissolved in water, a solution is
formed. This solution would be a homogeneous solution because it looks uniform throughout. You can
determine the solubility of a substance in a solution by determining how much of the substance
dissolves in another substance. Usually the substance that is present in the largest amount in a solution
is called the solvent, and the substance present in the least amount is called the solute. If a substance
does not completely dissolve or is not miscible in the solvent, a heterogeneous mixture may be formed.

When a substance (compound) dissolves in a solvent, it probably has similar physical and/or chemical
properties as the solvent. Sometimes we (chemists) say “like dissolves like”. For example, sugar and
water have similar chemical and structural features in common. Every compound has a maximum
solubility at a given temperature. That means you can only dissolve so much solute in a given amount of
solvent. You can dissolve a lot of sugar in 100 mL of water (10 grams per 5 mL water). If a compound
does not dissolve in a solvent they may not have similar chemical properties. For example, vegetable oil
and water are not miscible or soluble in each other because they have different properties.

Organic compounds that have both hydrogen bond donors and acceptors will be water soluble if they
have 5 carbons or less (more carbons if multiple H-bond donor acceptors present).
Examples of water soluble compounds with H-bond donors and acceptors:

Organic compounds that have only hydrogen bond acceptors will be water soluble if they have 3
carbons or less (more carbons if multiple H-bond donor acceptors present).
Examples of water soluble compounds with H-bond acceptors only:

The least soluble water soluble organic compounds are hydrocarbons and alkyl halides

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METHODS AND RESULTS:

In the following tables of solubility of organic compounds

I= Insoluble

SLS= Slightly soluble

S= Soluble

M= Miscible

IM= Immiscible

PART A:

TABLE 1: SOLUBILITY OF PHENOL

PROCEDURE OBSERVATION INFERENCE

A small quantity (20-25 mg) of At room temperature (cold) phenol did not S
“phenol” is transferred with spatula dissolve in water.
into a test tube and addition of about When the test tube was heated phenol
1mL of “water” and shaken thoroughly appeared to dissolve in water.
them warmed by heating test tube in
steam bath.
A small quantity (20-25mg) of At room temperature (cold condition), phenol S
“phenol” is transferred with spatula appeared to dissolve in cyclohexene by
into a test tube and 1mL of formation of golden solution.
“Cyclohexene” was added and shaken
thoroughly.

A small quantity (20-25mg) of At room temperature (cold condition) phenol S


“phenol” is transferred with spatula appeared to dissolve in Ethyl acetate by
into a test tube and about 1mL of formation of golden solution.
“EthyI acetate” is added and shaken
thoroughly.

A small quantity (24-25mg) of At room temperature (cold condition), phenol S


“phenol” is transferred with spatula appeared to dissolve in toluene by formation
into a test tube and about 1ml of of orange solution.
“Toluene” is added and shaken
thoroughly.

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PROCEDURE OBSERVATION INFERENCE

A small quantity ((20-25mg) of At room temperature (cold condition) SLS


“Naphthalene” is transferred into test Naphthalene did not dissolve in cyclohexene.
tube and about 1mL of “Cyclohexene” is When the test tube was heat, it appeared to
added, shaken thoroughly and then dissolve and form precipitate after some
heated in a steam bath. time.

A small quantity ((20-25mg) of At room temperature, Naphthalene did not I


“Naphthalene” is transferred into test dissolve in water.
tube and about 1mL of “water” is When the test tube was heated suspension
added, shaken thoroughly and then were formed.
heated in a steam bath.
A small quantity ((20-25mg) of At room temperature, Naphthalene appeared S
“Naphthalene” is transferred into test to dissolve and formation of clear solution
tube and about 1mL of “Ethyl acetate” is
added, shaken thoroughly.
A small quantity ((20-25mg) of At room temperature, Naphthalene appeared S
“Naphthalene” is transferred into test to dissolve and formation of clear solution.
tube and about 1mL of “Toluene” is
added and shaken thoroughly.

PART B:

TABLE 2: SOLUBILITIES OF 1-PROPANOL, 2-BUTANOL AND CYCLOHEXANOL IN H2O

PROCEDURE OBSERVATIION INFERENCE


1ml of 1-propanol was placed in attest tube A clear solution was formed. M
with a dropper, followed by addition of 1ml
of water and shaken thoroughly.
1ml of 2-butanol was placed in a test tube Two separate layers were formed IM
followed by addition of 1Ml of water with
dropper and shaken thoroughly.

1ml of cyclohexanol was placed in a test tube Two separate layers were formed. IM
followed by addition of 1mL of water with a
dropper and shaken thoroughly.

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PART C: 1

TABLE 3: SOLUBILITY OF PHENOL

PROCEDURE OBSERVATION INFERENCE

About 50mg of phenol was placed in test Formation of two separate layers.
tube, followed by 1mL of water and then Bottom layer being phenol and upper I
shaken thoroughly. layer being a solution of phenol.

About 50mg of phenol was placed in test Formation of two layers with some
tube, followed by addition of 1mL dilute amount of emulsion. I
HCl acid and then shaken thoroughly.

About 50mg of phenol was placed in test Dark green solution was formed
tube, followed by addition of 1mL NaOH
and then shaken thoroughly. S

About 50mg of phenol was placed in test Formation of two separate layers.
tube, followed by addition of 1mL
NaHCO3 and then shaken thoroughly. I

TABLE 4: SOLUBILITY OF BENZYL ALCOHOL

PROCEDURE OBSERVATION INFERENCE


1ml of Benzyl alcohol was placed in a Formation of emulsion milk in color IM
test tube followed by addition of 1mL of
water and then shaken thoroughly.

1ml of Benzyl alcohol was placed in a Formation of two separate layers IM


test tube followed by addition of 1mL of
dilute HCl acid and then shaken
thoroughly
1ml of Benzyl alcohol was placed in a Formation of two separate layers. IM
test tube followed by addition of 1mL of The upper layer was milk in color.
NaOH and then shaken thoroughly

1ml of Benzyl alcohol was placed in a Formation of two separate layers. IM


test tube followed by addition of 1ml of
NaHCO3 and then shaken thoroughly

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PART C: 2

TABLE 5: ACIDIFICATION OF NaOH OF PHENOL WITH DIL.HCl

PROCEDURE OBSERVATION INFERENCE

About 50mg of phenol were At room temperature phenol dissolved NaOH and M
introduced in a test tube acidified to form light pink solution.
followed by addition of 1mL
of NaoH, then acidified by
1mL of dilute HCl acid

PART D:

TABLE 6: SOLUBILITY OF CYCLOHEXANOL

PROCEDURE OBSERVATION INFERENCE


About 1mLof cyclohexanol was placed in - Formation of two separate IM
a test tube followed by addition of 1mL layers with emulsion
of water and then shaken thoroughly.

About 1mLof cyclohexanol was placed in - Formation of two separate IM


a test tube followed by addition of 1mL layers with emulsion
of dilute HCl acid and then shaken
thoroughly.

About 1mLof cyclohexanol was placed in - Formation of two separate IM


a test tube followed by addition of 1mL layers
of NaOH and then shaken thoroughly.

About 1mLof cyclohexanol was placed in - Formation of two separate IM


a test tube followed by addition of 1mL layers
of NaHCO3 and then shaken thoroughly.

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TABLE 7: SOLUBILITY OF ANILINE

PROCEDURE OBSERVATION INFERENCE


About 1mL of aniline was placed in a test - Formation of two separate IM
tube using a dropper followed by layers
addition of 1mL of water and then
shaken thoroughly.
About 1mL of aniline was placed in a test - Formation of two separate IM
tube using a dropper followed by layers
addition of 1mL of dilute HCl acid and
then shaken thoroughly.

About 1mL of aniline was placed in a test - Formation of two separate IM


tube using a dropper followed by layers
addition of 1mL of NaOH and then
shaken thoroughly.

About 1mL of aniline was placed in a test - Formation of two separate IM


tube using a dropper followed by layers
addition of 1mL of NaHCO3 and then
shaken thoroughly.

TABLE 8: SOLUBILITY OF BENZAMIDE:

PROCEDURE OBSERVATION INFERENCE


About 20mg of benzamide was placed in Suspension were formed
a test tube followed by addition of 1mL
of water and then shaken thoroughly. I

About 20mg of Benzamide was placed in Suspension were formed


a test tube followed by addition of 1mL
of water and then shaken thoroughly. I

About 20mg of Benzamide was placed in Suspension were formed


a test tube followed by addition of 1mL
of water and then shaken thoroughly. I

About 20mg of Benzamide was placed in Suspension were formed


a test tube followed by addition of 1mL
of water and then shaken thoroughly. I

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DISCUSSION:
This experiment was conducted to show solubility of some organic compound. Some of organic
compound appeared to dissolve at room temperature while some appears to dissolve at warm
condition. Consider the following table;

TABLE 9: General solubility of organic compound

Structure and name of the Expected solubility behavior according to the theory and experiment.
compound
Phenol Phenol is moderately soluble in water about 8g of phenol dissolved in
100mL of water. If exceeded more than that, two layers appear. It is
insoluble in NaHCO3 and soluble in NaOH,
It is soluble in aromatic hydrocarbon, alcohols, ketones, acids and
halogenated hydrocarbon.
Naphthalene Insoluble in water (3mg/100mL) and soluble in organic compound.

1-propanol Miscible in water because it has less than five carbon atom.

2-butanol Immiscible in water since increase in molecular weight leads to an


increase in intermolecular force in solid and decrease solubility.

Cyclohexanol Immiscible in water because it has six carbon atom.


Immiscible in dilute HCl, NaOH and NaHCO3.

Immiscible in water because has six carbon atoms. It is basic in nature,


only one aryl group being attached to the amino group hence insoluble
aniline in 5% sodium hydroxide and NaHCO3.

Benzyl alcohol Immiscible in water because it has more than five carbon atoms.
Immiscible in dilute HCl, NaOH, and NaHCO3

Benzamide Insoluble in water because has more than five carbon atoms.
Insoluble in 5% of sodium hydroxide sodium hydrogen carbonate
solution.

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CONCLUSION AND RECOMMENDATION


CONCLUSION

When two substances are mixed together they may form solution or may not dissolve in each other
depending on a variety of characteristics and properties associate with each properties of the substance.
From the experiment, it shows that solubility of organic compound involves the formation of one layer,
if the compounds are miscible or formation of two layers, if the compounds are immiscible.

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EXPERIMENT 2

CRYSTALLIZATION AND MELTING POINTDETERMINATION

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ABSTRACT:

This experiment aimed at determining crystallization and melting point of unknown compound. The first
part of this experiment involve carrying solubility test to find a suitable recrystallization solvent among
the given five solvent, such as water, methanol, P-Ether, Ethyl acetate and Toluene.

A small amount of impure sample was introduce in a test tube with addition of solvent and then shaken.
If all solid had nearly dissolved in a cold solvent and no precipitates, the solvent was considered
unsuitable. If not the mixture was heated gently to the boiling point with stirring in the steam bath. If
the most of the solid did not dissolve, the solvent was also unsuitable.

Ethyl acetate was found to be the best among the given solvents. Before preparation of the solution, the
mass of the remainder of unknown sample was recorded as 1.22g. A solute in a minimum of near boiling
point solvent is dissolved and the solution was allowed to cool slowly undisturbed to room temperature.
Once the crystal had formed a flask of crystallization solvent was placed in water-ice bath for a few
minutes. The crystal were collected by suction filtration and allowed to dry for one night. Before
determining the melting point range the mass of the purified sample was found to be 0.835g. so as to
determine the melting point range a small amount of the purified sample was introduced in a test tube
which was then placed in a melting point apparatus. The temperature at which the solid began to melt
and that at which it was completely liquid was recorded as the melting point range of the substance,
which was found to be 133-147.

The percentage yield was found to be 68.4%. It is recommended that the rate of heating is the most
critical factor affecting experimental results and should be carefully monitored particular close to the
expected melting point. Also careful transfer of the sample from one component to the other to avoid
loss of the sample.

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INTRODUCTION

The objective of this experiment is to determine the crystallization and melting point of unknown
compound. The hypothesis of crystallization and melting point determination is that recrystallization
help in purification of impure solid compound, also can be used to separate enantiomers from each
other while melting point verifies the purity of the compound and aids in the identification of unknown
compound. It is typically reported as the range where an impure solid will have a lower melting point
than the pure solid.

When a solid organic compound is prepared in the laboratory or isolated from some natural source,
such as leaves, it is almost always impure. A simple technique for the purification of such a solid
compound is crystallization.
The first part of this experiment involves carrying out solubility tests on known compounds. Later on
such solubility tests will be used to find a suitable recrystallization solvent for an unknown compound. A
compound usually exhibits one of three general solubility behaviors: (1), the compound has a high
solubility in both hot and cold solvent, (2), the compound has a low solubility in both hot and cold
solvent, and (3), the compound has a high solubility in hot solvent and a low solubility in cold solvent.
Solvents which exhibit the first two behaviors are not useful for recrystallizing a compound. A solvent
showing the third behavior, that is, high solubility at high temperatures and low solubility at low
temperatures, is one that is suitable for use as a recrystallization solvent.

Again solute in a minimum of near


boiling solvent is dissolved, allow the
solution to cool slowly and
undisturbed at room temperature
then possibly to rise temperature,
collect the crystals by filtration and
allow them to dry.

So as to determine the purity and


identify the compound melting
range must be determined.
Figure: …1……

In this report you will find a brief theory on crystallization and melting point together with the principle
used, experimental procedure, apparatus used, results and discussion of the results obtained during the
experiment, conclusion, recommendation and reference used.

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THEORETICAL PRINCIPLES

Crystallization is the process in which a solid compound precipitate from a saturated solution in the form
of crystals. During the process of crystal formation, a molecule will tend to become attached to a
growing crystal composed of the same type of molecule because of the better fit in crystal lattice for
molecules of the same structure than for other molecules. When the impure solid is dissolved in a
minimum volume of a suitable hot solvent and the resulting solution is gradually cooled, saturation and
eventually crystallization of the pure compound occurs.

Impurities are of two kinds: soluble and insoluble, recrystallization involves the removal of both to purify
a solid. Insoluble impurities are first remove by gravity filtration of the hot solution while the soluble
impurities remain dissolved in cold saturated solution after filtration of the desired compound. The pure
crystals are separated from the supernatant liquid by suction filtration. After drying, purify is checked by
a melting point determination.

Melting point is the temperature at which transition from solid to liquid occurs at atmospheric pressure.
Many organic compounds are solid at room temperature as the result of stronger intermolecular forces
which hold the individual molecules together in a crystal lattice. The nature and strength of the
intermolecular forces are responsible for the observed differences in melting point. The melting point of
a solid is practically unaffected by changes in external pressure making it a convenient physical constant
for the identification of solids.

The solubility of a solid solute in a solvent is determined by two factors:


a) The relative polarities of the solvent and solute. “Like dissolve Like” is the best summary of
solubility behavior. Polar solvent dissolve polar solute and non- polar solvent dissolve non-polar
solute.
b) The lattice energy of the crystalline solute. The crystal lattice, holding solute molecules together
in the solid state, is broken down upon dissolution. The stability of crystal lattice is roughly
reflected by the melting point.

A suitable solvent for crystallization should possess the following. Important properties;
a) Dissolve a large amount of the solid to be purified at high temperature, but very little at room
temperature.
b) Dissolve impurities readily at low temperature or not at all even when at the boiling point.
c) Not react with the substance to be purified.
d) Evaporate readily from the crystals.

If two or more solvent appear to be equally suitable, it is preferable to choose a solvent which is non-
flammable, non-toxic and cheap,

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EXPERIMENTAL PROCEDURE AND EQUIPMENTS:

MATERIAL AND APPARATUS


1. Test tube: used to study the solubility of impure substance.
2. Steam bath: used to heat the test tube containing the impure substance
3. Analytical balance: used to weigh the sample
4. Conical flask: used to heat the sample in water bath
5. Filter flask : used to filter crystal by vacuum filtration
6. Capillary tube :used to study the melting point of the sample
7. Melting point apparatus: used together with capillary tube to determine the melting point of
purified sample.
8. Buchner flask : used to collect crystals during suction.

METHODS:

EXERIMENTAL PROCEDURE:
The following steps were involved during recrystallization.
1) Selection of suitable solvent.
A small amount of the impure sample was introduced in a test tube with addition of solvent and
then shaken. If all sold had nearly dissolved in the cold solvent, the solvent was considered
unsuitable. If not the mixture was heated gently to the boiling point with stirring in the steam
bath. If most of the solid did not dissolve, the solvent was also unsuitable.

2) Preparation of the solution


The rest of the sample was weighed and transferred to the conical flask, where a small portion
of a selected solvent was added. The mixture was stirred and heated to boil where a small
portions of the solvent was kept added until all the solute dissolved. A slight excess of the
solvent was added to compensate for any losses (through evaporation) during filtration.

3) Cooling
So as to induce crystallization, the clear, hot filtrate was allowed to cool at cool at room
temperature, undisturbed until a large amount of crystals had formed. The mixture was finally
chilled in ice to complete crystallization.

4) Collecting and drying crystals.


The crystals were collecting by suction filtration using a Burner funnel to ensure rapid and
complete removal of the solvent. Finally crystals were dried in air by spreading them on the
paper for one night.

Figure 2 – Suction filtration

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5) Melting point determination


A small amount of a substance was introduced into a capillary tube which was then place in a
melting point apparatus. A melting apparatus was heated close to the melting point. The
temperature at which the sold began to melt and at which it was completely liquid was recorded
as the melting point range of the substance.

Calculations

Percentage purity Mass of the purified unknown


Of the purified = ----------------------------------------- × 100 %
Sample Mass of the crude unknown

0.835g
= ----------- × 100 %
1.22g

= 68.4 %

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RESULTS AND DISCUSSION

RESULTS:
Recrystallization of an unknown compound:

TABLE: Solubility of the given solvent

Water Methanol P. Ether Ethyl acetate Toluene


Solvent
cold Hot Cold Hot Cold Hot Cold Cold Cold Hot

Solubility I S S I I S S

Crystal YES. NO NO YES YES


Formation Faster Slowly Rapidly
S- Means soluble

I- Means insoluble

Suitable recrystallization solvent: Ethyl acetate

Mass of the crude unknown: 1.22g

Mass of the purified unknown: 0.835

% purity yield: 68.4%

Melting point range of pure unknown: 133-147 degree of Celsius

DISCUSSION

From trial and error technique, two solvents from the given list seemed to be good solvent, which are
water and Ethyl acetate. But ethyl acetate was found better than water due to the following reasons.

i) The boiling point of ethyl acetate is less compered to water. Since the boiling point of the
solvent should be low enough so that it can readily be removed from the crystals.
ii) Slow formation of crystal in ethyl acetate than in water when the hot solution is first cooled
slowly at room temperature and the place on ice.
iii) Rapid cooling of water than Ethyl acetate is undesirable because the crystals formed tend to
be very small and their resulting large surface area may foster adsorption of impurities from
solution.

The mass of the crude unknown was 1.22g and after purification was found to be 0. 835g and the
percentage recovery was 68.4 which show that, the recovery was not 100%. This is due to;

i) The low of sample during transferring from one flask to the other.
ii) Loss of weight from slightly solubility of solvent.

The melting point range seemed to diverge from 133-147 degree of Celsius this is due to density of
packing in capillary tube or thickness of the capillary tube.

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CONCLUSION AND RECOMMENDATION

CONCLUSION

Therefore the suitable solvent for the given unknown compound is Ethyl acetate where its boiling point
and melting point range are 78 °C and 133-147 °C respectively. The percentage recovery was
found to be 68.4% which means that the sample was lost.

RECOMMENDATION

Bear in mind, the melting point range is affected by number of factors in addition to that of purity.
Particle size, amount of the material used, the density of packing in the capillary tube and the rate of
heating the melting point apparatus, are all factors that should be carefully considered to ensure an
accurate melting point. The rate of heating the most critical factor affecting experimental results and
should be carefully monitored particularly close to the expected melting point.

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EXPERIMENT 3

SEPARATION OF A MIXTURE OF ORGANIC COMPOUNDS

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ABSTRACT

This experiment aimed at separating of a mixture of organic compound and identifying the separated
products. It involved four stages which are; Extraction, Recrystallization, melting point determination
and identification of the products.

Extraction: 1g of the given mixture was dissolved in 20mL dichloromethane. The solution was decanted
into separating funnel. Organic layer was extracted twice using 10mL 10% aqueous sodium bicarbonate.
The combined aqueous layer was cooled in an ice-water bath for 10 minutes eventually neutralized with
6M HCl. The precipitates were formed and collected by suction filtration. The organic layer was shaken
with 10mL saturated NaCl in a separated funnel and was dried with addition of anhydrous sodium
sulfate. The organic layer was decanted into a conical flask and solvent was evaporated using steam
bath.

Recrystallization: the separated products were recrystallized and weighed as 0.2312g and 0.1179g in
aqueous and organic layer respectively. The percentage yield was determined as 23% 12% in aqueous
and organic layer respectively. Also their melting points were determined.

Melting point determination: the temperature at which the solid stated to melt and that solid turned
into a liquid completely were recorded as 138-147®C and 109-119®C in aqueous and organic layer
respectively.

Identification of the product s:the solid in aqueous layer was white powder which was found to be O-
nitro benzoic acid and that in organic layer was white crystal which was found to be Acetanilide.

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INTRODUCTION

The objective of this experiment is separation of the mixture and identification of the separated
products. This involves three processes, which are; Extraction of the mixture, recrystallization of the
separated products and determination of melting point range of the products, finally identification of
the compound.

This technique is commonly used in isolation and purification of the products of the most organic
reactions. It is very rarely possible to identify the constituents of the mixture without separation. The
separation of the compound in a mixture should be as nearly quantitative as possible in order to give
some idea of the actual percentage of each component. This is done in four stages which are;
preparation of the separator funnel, adding the liquids, mixing the layers and separating the layers.

Recrystallization of the separated products: During this process of crystal formation, a molecule will
tend to become attached to a growing crystal composed of the same structure of molecule because of
the better fit in crystal lattice for molecules of the same type than of the other molecules. When the
impure solid is dissolved in a minimum volume of a suitable hot solvent and the resulting solution is
gradually cooled, saturation and eventually solution is crystallized by formation of pure compounds.

Melting point determination: Many organic compounds are solid at room temperature as the result of
strong intermolecular forces which hold the individual molecules together in a crystal lattice.
Determination of the melting point help in identification of the products separated from the mixture.

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THEORETICAL PRINCIPLES

Extraction is the separation of a substance from a mixture by means of a solvent that preferentially
dissolves that substance. If the substance is extracted from a solid phase, the process is called solid-liquid
extraction, as in the isolation of caffeine from tea leaves by means of hot water. Extraction of a substance
from a liquid phase is called liquid-liquid extraction. The most common applications of this latter
technique are:

a. The recovery of an organic product from a reaction mixture containing excess unreacted
materials and by-products.
b. Isolation of an organic substance from its natural source, such as a plant.

Liquid-Liquid Extraction: This is the most common type of extraction. It involves shaking the liquid
mixture with an immiscible solvent which preferentially dissolves the desired compound. On standing,
the two immiscible phases (usually organic and aqueous) form two separate layers (upper and lower) that
can be separated by means of a separator funnel. The various solutes in the mixture distribute themselves
between the organic and aqueous phases according to their relative solubility in each solvent. At
equilibrium, the ratio of the concentration (C) or solubility (S) of the substance in the organic phase, (Co
or So) to that in the aqueous phase (Cw or Sw) is called the distribution coefficient (KD)

A large distribution coefficient implies that the compound is much more soluble in the organic phase than
in the aqueous one and, in this case, a single extraction suffices to remove the desired compound from the
mixture. When KD is small, it means that the compound distributes itself more evenly in both phases, so
that repeated extractions are required to recover such a compound from the aqueous mixture. In general, it
is more efficient to divide the total volume of extracting solvent over several extractions than to use the
whole volume in a single extraction.

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EXPERIMENTAL PROCEDURE AND EQUIPMENTS

APPARATUS:
1. Separating funnel
2. Buchner funnel
3. Buchner flask
4. Measuring
5. Conical flask
6. Beaker
7. Dropper
8. Spatula
9. Melting point apparatus
10. Analytical balance.
11. Steam bath
12. Capillary tube.

EXPERIMENTAL PROCEDURE

1. Mixing the layers:

1g of the given mixture was dissolved in 20mL dichloromethane. The solution was decanted from beaker
into separating funnel. By using 10mL 10%aqueous sodium bicarbonate the organic layer was extracted
twice as follows;

The stopper was inserted and by holding the stopper in the place will one hand, a separator funnel was
pecked up and inserted. Immediately the stopcock was opened with other hand so as to vent solvent
fumes or carbon dioxide. The separator funnel was swirled gently to further drive off solvent vapors or
gases.

After venting, the stopcock was closed and the mixture in the inverted funnel was gently shaken up and
down vigorously in a somewhat circular motion for 2-3 minutes so that the layers are thoroughly mixed.
The stopcock was vented several times during shaking.

A conical was placed under the stem of the separator funnel in case the stop cock would have developed
a leak. The separator funnel was allowed to sit until the layers had separated.

2. Separating the layers:

Before proceeding, the stopper was first removed (It is difficult to drain the lower layer from a
stoppered funnel. Because a vacuum is created in the top potion of the funnel)

The aqueous layer was combined and labeled as SOLUTION 1.

3. Cooling and neutralization of aqueous layer.

The aqueous layer was cooled in ice-water bath for 10 minutes. After cooling, it was neutralized by
adding 6M HCl, where precipitates formed.

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4. Collecting and drying the precipitates of aqueous layer:

The precipitations were collected by suction filtration using a Buchner funnel to ensure rapid and
complete remove of the solvent. Finally precipitates were dried in an air by spreading them on the sheet
of paper for one night.

5. Shaking the organic layer.

The organic layer was shaken with 10mL saturated NaCl in a separating funnel. By repeating the same
procedure in (1) above, the organic layer was extracted and labeled SOLUTION 2. The organic layer was
dried by addition of anhydrous sodium sulfate. The dried organic layer was decanted into a dry conical
flask. The solvent was evaporated using steam bath. The crystals were collected by suction filtration and
finally dried in air.

6. Melting pint determination.

Before melting point determination, the mass of each pure sample were recorded. A small amount of
each sample was recorded. A small amount of each sample was introduced in a capillary tube which was
then placed in a melting point apparatus. The temperature at which the soled began to melt and at
which it was completely liquid, was recorded as the melting point range.

Calculations:

Amount recovered (mg)

Percentage recovery = ------------------------------ X 100 %

Amount dissolved (mg)

% recovery in aqueous = 0.23 x 100% = 23 %


layer 1

% recovery in organic = 0.118 x 100 % = 12 %


layer 1

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RESULT AND DISCUSSION

Acid component : Structure:

Name: O-nitro benzoic acid

Weight recovered: 0. 2314g

% recovery: 23 %

Melting point; expected: 147 ®C

Found: 138- 147 ®C

Appearance: White powder

Neutral component: Structure:

Name: Acetanilide

Weight recovered: 0.1179g

% recovery: 12 %

Melting point; expected: 113-114 ®C

Found: 109- 119 ®C

Appearance: white crystals

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DISCUSSION

It is important to identify the solvent in each layer. Dichloromethane is denser than water, when it was
dissolved as the non-polar solvent water layer appeared on top. To confirm the identities of the layers,
one or two drops of water are introduced just below the surface of the top layer. If the drops of water
fall through the top layer below, then the water layer is the bottom one.

The mass of the crude/mixture was 1g, after purification and separation the masses were as follows:
0.2312g and 0.1179g in aqueous and organic layer respectively. These masses yield 23% and 12%
respectively, which is not 100% of recovery. This is due to the following reasons;

a) Poor decantation during the experiment.


b) Loss of the sample during the experiment (from one component to another)

The melting point of O-nitro benzoic acid started from 138-147®C and that of Acetanilide was 109-
119®C. this ids due to the presence of impurities in the purified sample which tend to lower the melting
points. Also it is contributed to the tare of heating of the melting point apparatus.

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CONCLUSION AND RECOMMENDATION

CONCLUSION

Therefor this given mixture contains O-nitro benzoic and acetanilide which melt at 138-147®C and 109-
119®C respectively. The small range between melting points is due to left impurities in the purified
sample.

RECOMMENDATION

 Be sure to close the stopcock at the bottom of the separator funnel before adding solution
 Acetanilide is toxic irritating. Keep away from flames or other heat sources.
 The solid may take 5 minutes or more to dissolve. You should stir the mixture during this time.
 Do not open the stopcock while the glass stopper is in the top of the separator funnel, a slight
vacuum will be created and the bottom layer will not drain from the funnel.
 Anhydrous sodium sulfate (Na2SO4) is irritating and hygroscopic. Prevent eye, skin and clothing
contact.
 The rate of heating should be controlled so that the melting range is as narrow as possible.

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EXPERIMENT 4

CHEMISTRY OF FUNCTIONAL GROUP

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ABSTRUCT:

This experiment aimed at passing through organic compound reactions basing on functional group. The
chemistry of functional group which we are dealing with are; hydrocarbons, alcohols, phenols and
halogen compounds.

Hydrocarbons: The provided hydrocarbons are Toluene, phenyl acetylene, cyclohexene and n-Heptane.
Different test were performed on each hydrocarbon compound given. These are the tests which were
performed; Action of bromine, the positive test were observed on hydrocarbon with multiple bond (
double and triple bonds ) which are phenyl acetylene and cyclohexene. Action of copper chloride, only
phenyl acetylene had positive test due to terminal acidic hydrogen. KMnO4 test, the positive tests were
observed on hydrocarbon with multiple bonds which were oxidized. And these are phenyl acetylene and
cyclohexene.

Alcohols: The provided alcohols are; 1-propanol, 1-butanol, 2-butanol, t-butanol and cyclohexanol. Iodo
form test was performed on each alcohol to test for terminal methyl group. Only t-butanol and 2-
butanol had positive test while the rest had negative test.

Phenols: The provided compound are phenol and resorcinol. Different tests were performed on each
phenol group given, and these are tests which were performed; Neutral FeCl3, both phenols had
positive test. KMnO4 test, both phenols had positive test with formation of carbonyl compound after
being oxidized. Ag(NH3)2 test, only phenol had positive test.

Halogen compounds: Two halogen compounds were provided, these are t-butyl chloride and Chloro
benzene. Also different tests were performed. Action of water, both of them had positive test on water
with formation of acid (HCl) which changed litmus paper blue to red. Alcoholic silver nitrate test, only t-
butyl chloride had positive test where AgCl were given out as white precipitate.

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INTRODUCTION

The purpose of this experiment is to go through reactions of some important functional group in
counted in organic chemistry and to recognize the importance of functional group reactions in the
identification characterization of organic compounds. Because functional groups influence the physical,
chemical, and spectral properties of an organic compound, a chemist can identify a compound's
functional groups by measuring certain physical properties, observing its chemical behavior with
different classification reagents, and studying other spectral data.

This predictable reactivity allows a chemist to attempt a variety of reactions on an organic compound
and determine what functional group(s) are present. To use any reaction as a test fora functional group, it
is necessary for the product mixture to appear significantly different fromthe reactants. This may be due
to formation of a precipitate or colored product, or it may bedue to consumption of a solid or colored
reactant .This may be due to formation of a precipitate, colored product or consumption of a solid/
colored reactant.

Within this report you will find a clear procedure, observation, inference3 and chemical equations
involved in different tests of some organic compounds. The compounds to be tested are hydrocarbon,
alcohols, phenol and halogen compounds.

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THEORETICAL PRINCIPLES:

A functional group is a portion of a molecule that is a recognizable/classified group of bound atoms or


specific groups of atoms within molecules that are responsible for the characteristic chemical reactions
of those molecules.Rigorously speaking the functional group is not the whole molecule but only that
collection of atoms that provides a specific chemical function. For example, the chemical family of
alcohols is characterized by the function of the hydroxyl (OH) group, and aldehydes, ketones are
characterized by carbonyl groups (C=O). In organic chemistry it is very common to see molecules
comprised mainly of a carbon backbone with functional groups attached to the chain. The functional
group gives the molecule its properties, regardless of what molecule contains it, also they are centers of
chemical reactivity.
.
Theory behind Functional Group:

a. Solubility Tests for Carboxylic Acids, Phenols, Amines and Small Molecules
The solubility of an organic compound in water depends on both its size and polarity.
Compounds with 4 carbons (or less) and at least one polar functional group tend to be water soluble.
Larger compounds tend to be insoluble in water unless they have an ionized functional group or several
polar functional groups. Thus, an insoluble compound can be made water soluble if one of its functional
groups can be ionized. For example, amines are weak bases. If an insoluble amine is reacted with strong
acid, the amine will be protonated and become soluble in water. Similarly, carboxylic acids and phenols
are weak acids. If an insoluble phenol is reacted with strong base, the phenol will be deprotonated and
become soluble in water. Finally, phenols are much weaker acids than carboxylic acids. As such, there
are some bases that are strong enough to deprotonate a carboxylic acid but not a phenol. One such base
is NaHCO3 (which will make a carboxylic acid soluble in water but not a phenol).

b. Bromine Test for Alkenes and Alkynes


Most halogens (chlorine, bromine and iodine) react readily with carbon-carbon multiple
bonds that are not part of an aromatic ring. In order to determine whether or not the reaction has
proceeded, it is therefore necessary to look at the halogen. Chlorine is a green gas, bromine a dark
brown liquid and iodine a purple-black solid. Bromine is typically chosen as the test reagent for alkenes
and alkynes because, if it reacts, its rich brown color will disappear. If there the brown color persists, it is
because there are no alkenes or alkynes for the bromine to react with.

c. Lucas Test for Alcohols (2° and 3°)


Alcohols are very weak bases (comparable to water) which react slightly with strong acids.
The product of such a reaction is an electrophile with a very good leaving group. In the presence of a
good nucleophile, a substitution reaction results. This is the basis of the Lucas test. Tertiary alcohols (in
which three carbon atoms are attached to same carbon as the –OH group) react very quickly in the
Lucas test, producing alkyl halides that are insoluble in the aqueous Lucas reagent. Secondary alcohols
(in which two carbon atoms are attached to same carbon as the –OH group) react more slowly while
most primary alcohols (only one carbon atom is attached to the same carbon as the –OH group) do not
react at all.
Because a positive test is indicated by formation of a product that is insoluble in water, the
Lucas test is only useful for compounds that are water soluble.

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EXPERIMENTAL PROCEDURE AND EQUIPMENTS

APPARATUS:

 Test tube: used to test the reactions of the substance


 Test tube holder: used to hold the test tube for further warm
 Measuring cylinder: used to measure the required amount of compound

Steam bath: used to warm the contained test tube

 Dropper: used to take a required compound from its container


 Ice-water bath: used to cool the test tube
 Litmus paper: used to test the acidity and the basic of reactions

PROCEDURE

1. Test on hydrocarbons:
1.1. Action of bromine:

The compound was dissolved in carbon tetra chloride with addition of bromine solution. Simultaneously
a blank test was run with solvent ( CCl4) alone. Where there was no decolonization, the solution was
exposed to the strong light ( sun light ) for few minutes. And if there was any change was recorded.
Again a wet litmus paper was inserted into the mouth of the tube and color change was observed.

1.2. KMnO4 test:

The compound was dissolved in 1 mL of acetone with addition of 1-2 drops of dilute KMnO4.
Simultaneously a blank test was run with solvent alone (acetone and KMnO4). And finally a compound
which decolorized the color of MnO4 was recorded.

1.3. Action of copper chloride:

First, a reagent was prepared as follows; about 1-2 mL of 10% copper sulphate solution was added in 5
mL dilute ammonia until the initial precipitate dissolved and a clear solution was obtained. A solution of
hydroxyl amine was added drop by drop while shaking until the solution became first green and then
completely colorless.

A portion of a prepared reagent was added to alcoholic solution of each hydrocarbon and shaken. And
there were observation of precipitate formation.

2. ALCOHOLS:
Iodoform test:

A mixture of about 10 drops of alcohol and 1mL of 10% KI was warmed drop wise about 1mL NaOCl
solution was added. Color changes were observed.

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3. PHENOLS:
3.1. Neutral FeCl3 test.

An aqueous solution of 1mL FeCl3 solution was treated drop wise with a dilute 0.1N Sodium hydroxide
solution until a faint precipitate was observed. Few drops of the neutral FeCl3 solution were added to a
neutral aqueous solution of phenol.

3.2. Bromine water test:

About 1mL of bromine water were added few drops of phenol and shaken.

3.3. KMnO4 test:

A compound was dissolved in 1mL acetone with addition of 1-2 drops of dilute KMnO4. Simultaneously a
blank test was run with solvent alone (acetone and KMnO4). The compound which decolorized the color
of MnO4 was recorded.

3.4. Ag(NH3)2 test.

First, the Tollen’s reagent was prepared. 6 drops of NaOH were added into 1mL aqueous AgNO3 followed
by dilute ammonia solution drop wise until the precipitate Ag2O were just dissolved.

Phenol was tested with litmus paper to observe if it is acidic or not. If acidic NaHCO3 solution was added
drop wise with shaking until the solution was just alkaline. The resulting solution was tested with few
drops of Tollen’s reagent and shaken thoroughly.

4. HALOGEN COMPOUNDS:
4.1. Action of water.

In a test tube of 1mL of water, few drops or about 100mg of the compound were added and shaken.
Solubility of the compound was observed together with any sign of reaction (eg. Evolution of heat). The
solution was tested with blue litmus paper.

4.2. Alcoholic silver nitrate

In 1mL ethanol, 10 drops of each compound was dissolved in separate test tubes. Into each, about
0.5mL alcohol AgNO3 solution was added and it was allowed to stand. The rate of AgCl precipitate
formation was observed.

4.3. Action of hot NaOH.

In separate test tube, about 10 drops of each compound was dissolved in 1mL mixture of 1:1 ethanol 2N
NaOH solution and boiled to about 1 minute. Then it was cooled, the solution was acidified with about
1mL dilute nitric acid together with addition of aqueous AgNO3.

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RESULTS AND DISCUSTION:

Experiment 4 part A results: Test on hydrocarbons.

1. Action of bromine
Test substance Observation Inference Equation

Toluene Dissolved in CCl4. Negative No reaction.


After addition of Bromine two test.
layers were formed, where by the
bottom layer was brown and top
was cloudy.
Phenyl acetylene Dissolved in CCl4 and after Positive
addition of bromine, the color of test
bromine disappeared and yellow
precipitates were observed after
being exposed to sun light.

Cyclohexene Did not dissolve in CCl4, on Positive


addition of bromine color test
changed to colorless and two
layers formed.

n- Heptane Dissolved in CCl4 Negative No reaction


When bromine was added, the test
color of bromine was retained
and when it was exposed to sun
light excess bromine evaporated.
Tetra Chloride Formation of two layers when Negative No reaction
( CCl4) dissolved in bromine, where test
Blank test bottom was brown and top was
CCl4 color.

2. KMnO4 test
Test substance Observation Inference Equation

Toluene Dissolved in acetone, when Negative No reaction


KMnO4 was added two layers test
formed

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Phenyl acetylene Dissolved after acetone was Positive


added. test
When KMnO4 was added
brown precipitates were
formed and color of KMnO4
was decolorized.
Cyclohexene Dissolved in acetone .when Positive
KMnO4 was added the solution test
changed to brown and
precipitates were formed.

n- Heptane Formed two layers with Negative No reaction


acetone. test
When KMnO4 was added, two
layers formed.
Acetone When KMnO4 was added into Negative No reaction
acetone two layers formed, test
where by the top layer was
colorless and bottom was
purple.

3. action of copper Chloride

Test substance Observation Inference Equation

Toluene Formation of two layers Negative No reaction


test

Phenyl acetylene Yellow precipitate were formed Positive


test

Cyclohexene Formation of two layers Negative No reaction


test

n- Heptane Formation of two clear layers Negative No reaction


test

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Experiment 4 part B results: Reactions of Alcohols

Iodoform test ( KI and NaOCl )


Test Observation Inference Equation
substance
1-propanol Formed a clear solution after addition Negative No reaction
KI at room temperature and remain test
the same after warm.
On addition of NaOCl, clear solution
formed.

1-butanol On addition of KI formed two colorless Negative No reaction


separate layers at room temperature test
and remain the same after warm.
When NaOCl was added a colorless
solution was formed.
2-butanol Two layers were formed on addition of Positive
KI. After addition of NaOCl, two layer test
were formed, one of yellow ppt and
another colorless

t- butanol On addition of KI a clear solution was Positive


formed at room temperature and test
remained the same after warm. It
formed a yellowish and changed to
colorless.
Cyclohexanol On addition of KI, a clear solution was Negative No reaction
formed. After addition of NaOCl it test
formed an orange color solution.

Experiment 4 part C results: Reactions of Phenols

1. Neutral FeCl3 test


Inference
Test substance Observation Equation
Phenol Formation of purple Positivetest
precipitate
Violet color appear

Resorcinol Formation of purple Positive


precipitate test
Deep violet color
Appear

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2. KMnO4 test

Inference
Test substance Observation Equation
Phenol Dissolved and there was Positive
formation of grey test
solution

Resorcinol Dissolved in acetone Positivetest


Black precipitate formed
at the bottom after
addition of KMnO4

3. Ag(NH3)2 test

Inference
Test substance Observation Equation
Phenol Was acidic for litmus paper Positive
On addition of NaHCO3 became test
alkaline and precipitate were
formed.

Resorcinol No acid Negative No reaction


test

Experiment 4 part D Result: Reaction of halogen compound

1. Action of water

Test substance Observation Inference Equation

t- butyl chloride Two layers were formed on Positive


addition of water test
Litmus paper changed from blue to
red

Chloro benzene Two layers were formed Positive


Litmus paper changed from blue to test
red.

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2. Alcoholic silver Nitrate

Test substance Observation Inference Equation

t- butyl chloride Dissolved in ethanol Positive


Formation of white precipitate on test
addition alcoholic AgNO3

Chloro benzene Dissolved in ethanol Negative


Formed two layers on addition of test
AgNO3

3. Action of hot NaOH

Test substance Observation Inference Equation

Chloro benzene On addition of dilute nitric acid Positive


heat evolved and dark brown test
precipitates were formed after
addition of silver nitrate

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CONCLUTION AND RECOMMENTIONS

CONCLUSION:

The study of function group is based on α-carbon and β-carbon. α-carbon is carbon which carry the
functional group and β-carbon is the carbon next from α-carbon. From these tests it shows that most of
the functional group have atoms which are more electronegative. These more electronegative atoms
draw electrons by negative inductive effect away from the functional group. Extent to which negative
inductive effect is significant is only to the β-carbon.

RECOMMENDATION

 After each of your chemical test is complete, dispose of the chemicals and disposable test tube
in the waste container in the hood where the test was conducted.
 Dispose of any of your unused unknown chemical after you are sure of its identity in the waste
container and place the empty vial in the collection bin provided.
 Do not mix up the unknown vials with the new ones.
 Bromine is corrosive handle it with care.
 Do not exceed the required amount on the test.

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APPENDICES:

REVISTION QUESTIONS AND ANSWERS:

1. A mixture of benzoic acid, aniline and phenol is dissolved in chloroform and the solution is
treated with NaOH, HCl and NaHCO3. Show a separation chart, identify the composition of each
phase and explain the chemistry of the separation process.
Answer:

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2. Why is gravity filtration and not suction filtration used to remove suspended impurities and
charcoal from a hot solution?

ANSWER:

Under suction a hot solution is likely to boil due to lower pressure of the suction flask. Then you would
have sucking lots of vapor lather than liquid. By evaporation of the liquid, this would also decrease the
solution temperature and increase the concentration of the solute, which could cause some of the
solute to precipitate out of solution.

3. An unknown sample was crystallized from benzene. On cooling to 0 °C in ice bath the amount of
crystal in flask was quite large, but much of it seemed to disappear when an attempt was made
to collect it by suction filtration. Explain.

ANSWER:

Under suction filtration a hot solution is likely to boil. Then would be sucking lots of vapor rather than
liquid, because by evaporating liquid decrease the solution temperature and increase the concentration
of solute which could cause some of the solute to precipitate out of benzene solution.

4. What is the reason for activated carbon during crystallization? Why is recommended to use little
and not a lot during process.

ANSWER:

Activated carbon is used to remove the colored impurities from the sample. Activated carbon provides a
high surface area to absorb colored impurities. It is recommended to use little because when you add to
much the significant amount of the desired compound will also be absorbed and low recovery will
result.

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5. Draw a flow chart for the separation of the given organic mixture in this experiment.

Answer

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6. You are provided with two test tubes, each containing one or pair of compound. Outline a
simple chemical test/ experiment you would perform to distinguish between the compounds.
Write balanced equations for reactions you expect to take place in your test.
a)

and
Answer: Reaction with Cl2 under UV light, which will yield HCl acid detected by color change of
litmus paper.

, but

b) and

Answer: Reaction with Ammoniacal silver nitrate. Is a compound with a general formula of
[Ag(NH3)2]NO3 . Alkynes with terminal acid hydrogen react with ammoniacal silver Nitrate solution to
form a white precipitate of alkalide.

, but

c) and

Answer: Test of phenolic solution by using Ferric ions (Fe2+), this will give purple colorization on the
addition of ferric ions to phenolic solution. First dissolve FeCl3 in water to give ferric hydroxide Fe(OH)3

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REFERENCES:

1. Grovedd. 2009. Separating Acids and Neutral Compound by solvent Extraction. GPL
Glostscript 8.15

2. Wheel, e. 2011. Organic chemistry laboratory procedure.

3. Lawton show, Drscott MC Gavin. 2011. Organic chemistry 11, Report Book. Athabasca
university.

4. Andyint, A. 2009. An introduction to Functional group in organic chemistry. Microsoft office


word 2007.

5. H. Controy, A. Raphael.1960. Advanced in organic chemistry: Methods and Results.ed E.C


Taylor. New York.

6. Emerson.L.; Hampton, J. Writing Guidelines for science and Applied Science.

7. M. Jones and S.A. Flewing, “Organic chemistry” Norton, 4thedn.,pp 14-16.

8. King Abdul Aziz University. 2010. Fundamental organic chemistry. Department of chemistry.

9. Peter Samal. 2010. Rerystallization. Mac OSX 1064 Quartz PDF context.

10. Tim Minger,. 2009. Crystallization (Recrystallization and melting point Determination.
Acrobat Distiller 6.0.1 (windows).

11. Stainislawskonieczny. 2008. Recrystallization. Acrobat PDF Distiller 7.0 (windows).

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EXPERIMENT I ............................................................................................................................................... 1
SOLUBILITY OF ORGANIC COMPOUNDS ....................................................................................................... 1
ABSTRACT.................................................................................................................................................. 2
INTRODUCTION: ........................................................................................................................................ 3
THEORETICAL PRINCIPLES ......................................................................................................................... 4
METHODS AND RESULTS:.......................................................................................................................... 5
DISCUSSION:............................................................................................................................................ 10
CONCLUSION AND RECOMMENDATION ................................................................................................ 11
EXPERIMENT 2 ............................................................................................................................................ 12
CRYSTALLIZATION AND MELTING POINT DETERMINATION ....................................................................... 12
ABSTRACT:............................................................................................................................................... 13
INTRODUCTION ....................................................................................................................................... 14
THEORETICAL PRINCIPLES ....................................................................................................................... 15
EXPERIMENTAL PROCEDURE AND EQUIPMENTS: .................................................................................. 16
RESULTS AND DISCUSSION...................................................................................................................... 18
CONCLUSION AND RECOMMENDATION ................................................................................................ 19
EXPERIMENT 3 ............................................................................................................................................ 20
SEPARATION OF A MIXTURE OF ORGANIC COMPOUNDS .......................................................................... 20
ABSTRACT................................................................................................................................................ 21
INTRODUCTION ....................................................................................................................................... 22
THEORETICAL PRINCIPLES ....................................................................................................................... 23
EXPERIMENTAL PROCEDURE AND EQUIPMENTS ................................................................................... 24
RESULT AND DISCUSSION ....................................................................................................................... 26
CONCLUSION AND RECOMMENDATION ................................................................................................ 28
EXPERIMENT 4 ............................................................................................................................................ 29
CHEMISTRY OF FUNCTIONAL GROUP ......................................................................................................... 29
ABSTRUCT: .............................................................................................................................................. 30
INTRODUCTION ....................................................................................................................................... 31
THEORETICAL PRINCIPLES: ...................................................................................................................... 32
EXPERIMENTAL PROCEDURE AND EQUIPMENTS ................................................................................... 33
RESULTS AND DISCUSTION: .................................................................................................................... 35
CONCLUTION AND RECOMMENTIONS ................................................................................................... 40

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APPENDICES: ............................................................................................................................................... 41
REVISTION QUESTIONS AND ANSWERS: ................................................................................................. 41
REFERENCES: ............................................................................................................................................... 45

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