EXERCISE 1

PROPERTIES THAT DISTINGUISH ORGANIC FROM INORGANIC COMPOUNDS

Organic Compounds Inorganic Compound

Flammable yes no

Melting Point low high

Boiling Point low high

Solubility in water no (for most) yes

Solubility in non-polar liquids yes no

Type of bonding covalent ionic

Reactions occur between: molecules ions

Atoms per molecule many few

Structure complex simple

Electrolyte no yes

 Organic compounds are unstable. They are combustible, with many having no sharp
melting points, decomposing, and charring at moderately high temperature.
 Most are non-electrolytes.
 Most organic compounds contain the same kind and number of atoms but they exhibit
different sets of properties.
 Organic chemical reactions are relatively slow.

Name of Test
Test Compound Result
Ignition Tests
a. Flammability Ethyl alcohol Flammable
Water Non-flammable
b. Charring Sucrose Positive
C12H22O11 + O2 + heat → CO2↑ + 11H2O↑ + 11C↓
Sodium chloride Negative
Calcium carbonate Negative
 Name of Test Test Compound Observation Type of Bond
Solubility Tests Naphthalene in water Insoluble
Naphthalene in ether Soluble Covalent bond
Urea in water Partially soluble H-bonding
Urea in ether Soluble Covalent bond
Sodium chloride in water Soluble Ionic bond
Sodium chloride in ether Insoluble

Name of Test Test Compound Observation

Electrical Conductivity 1M sucrose Non-electrolyte
1M sodium chloride Electrolyte
95% ethyl alcohol Non-electrolyte
n-hexane Non-electrolyte
EXERCISE 2

QUALITATIVE TESTS FOR ELEMENTS IN ORGANIC COMPOUNDS

 Carbon and hydrogen are the predominant elements found in organic compounds.
 Next common elements are: oxygen, nitrogen, sulfur, phosphorus, halogens – chlorine,
bromine, and iodine.
 Least common elements include: arsenic, antimony, mercury, and other metals.

A. Test for Carbon and Hydrogen

Test compound: Glucose (C6H12O6)

 Carbon and hydrogen are detected qualitatively by heating a mixture of the given
substance with dry copper (II) oxide in a glass tube.

C6H12O6 + CuO → CO2↑ + H2O

CO2 + Ca(OH)2 → CaCO3↓ + H2O

Glucose + CuO

heat

CO2 water vapor

gets trapped in lime water

Calcium carbonate Water

 The presence of carbon is indicated by the formation of white precipitate.

 The presence of hydrogen is indicated by the formation of droplets of water in the cool
end of the tube.
 Copper (II) oxide acts as a catalyst.
B. Test for Nitrogen

Name of test: Soda-Lime Test

Test compound: Urea

 Soda-lime: NaOH-CaO (2:1 solid mixture)

 Nitrogen is usually detected by the formation of Prussian blue after the sodium fusion.

CO(NH2)2 + heat → NH3↑ + CO2

CO2 + Ca(OH)2 → CaCO3↓ + H2O

 When heated with soda lime, urea decomposes and the nitrogen in the form of amino
nitrogen (-NH2) will liberate ammonia gas.
 Red litmus paper changes to blue.

C. Test for Halogen

Name of test: Beilstein Test

Test compound: Chloroform (CHCl3)

 An organic halogen compound imparts a green color flame when burned upon the
surface of a copper wire.
 The copper oxide formed from the copper wire reacts with the halogens to form the
cuprous halide, which burns with a green flame.
 Chlorine is the compound responsible for turning the flame green.

Name of test: Silver Nitrate Test

Test compound: Monochloroacetic acid

 Formation of insoluble silver halide upon treatment with silver nitrate in the presence of
dilute nitric acid.
 Nitric acid is necessary to remove cyanide and sulfide ions, otherwise, they form
precipitates – silver cyanide is white and silver sulfide is black – that interfere with the
detection of halogens.
 Silver chloride – white precipitate.
D. Test for Oxygen

Name of test: Ferrox Test

Test compounds: Acetone, ethyl alcohol, gasoline, benzene

 Ferrox paper is prepared by soaking filter paper in methanol containing equal amounts
of ferric chloride and ammonium thiocynate.
 In the presence of oxygen, a deep red color is distributed between the filter paper and
the test compound.
 The test showed positive results for acetone and ethyl alcohol.

E. Test for Sulfur

Name of test: Lead Acetate Test

Test compounds: Albumin

 The presence of sulfur is detected by the production of brownish-black lead sulfide

when albumin is treated with lead acetate in the presence of acetic acid.
 Acetic acid prevents the formation of other insoluble lead salts.
 The production of brownish-black precipitate is due the presence of cysteine – the
amino acid part of albumin.
 EXERCISE 3

Separation and Purification of Organic Compounds

QUALITATIVE TESTS FOR ELEMENTS IN ORGANIC COMPOUNDS

 Recrystallization is a highly effective method for the purification of organic substances

that exists already as crystals.

Processes Involved in Recrystallization

1. Dissolving the material to form a saturated solution in a suitable solvent at an
elevated temperature.

Properties of a Desirable Solvent

a. Dissolves the solute easily at an elevated temperature, but only sparingly
at a lower temperature.
b. Gives no chemical reaction with the solute.
c. Sufficiently volatile so that it may be removed easily from the purified
crystals.

2. Filtering while hot to remove any suspended insoluble particles.

3. Letting crystallization process

Stages of Recrystallization
1. Removal of impurities, which may retard or inhibit crystal formation.
 Samples that contain colored impurities maybe treated with decolorizing
carbon to give rise to colorless solution.
 Impurities are adsorbed by the active surface of the
decolorizing carbon.
 Animal charcoal is less effective at high than at low
temperature.
 The reason for operating at high temperature is to keep the
substances from being crystallized in solution.

2. Nucleus formation
 Spontaneous nucleus formation is caused by the orientation and aggregation
of sufficient number of molecules, which may give rise to a crystal nucleus.

Methods of Inducing Crystal Formation

1. Seeding – the process of adding a small crystal of pure material to induce
the crystallization process.
2. Scratching the sides or bottom of a container with a glass rod – provides
sharp edges upon which crystal growth may occur.
 3. Encouragement of growth of crystals to visible form.
 Growth of crystals maybe encouraged by stirring or agitation, which results in
distribution of the nuclei throughout the solution.
 Crystal growth in supersaturated solutions may be inhibited as
a result of restricted motion of the molecules.

A. Recrystallization of Benzoic Acid

Benzoic acid + NaCl + Methylene blue

heat

+ activated charcoal

filter

activated charcoal + methylene blue colorless solution

rapid cooling slow cooling

water coarse crystals water fine crystals

wash with cold distilled water

Benzoic acid crystals Benzoic acid crystals

+ +
hot distilled water hot distilled water
+ +
HNO3 HNO3
+ +
AgNO3 AgNO3

Colorless solution Colorless solution

with crystals with crystals

Cloudy solution: NaCl + AgNO3 → NaNO3 + AgCl

B. Decolorization of Brown Sugar

Brown sugar + water

Brown sugar solution Brown sugar solution

Heat

+ Activated carbon

filter

activated charcoal + brown pigment Colorless solution

 EXERCISE 4

Separation and Purification of Organic Compounds

SUBLIMATION

 Sublimation – the direct conversion of a substance from solid to gas without passing
through the liquid state.
o It can be applied when the components of a solid mixture differ appreciably in
their vapor pressures.
o As a separation process, it involves gentle heating of the mixture in a confined
container until the component with high vapor pressure changes into vapor
phase, while the component with the lower vapor pressure is left in the
container.
o As a purification process, it also depends on the difference of volatility. Less
volatile or non-volatile impurities remain as residue while the sublimate is being
formed.
 Sublimate – the crystals, deposit, or material obtained when a substance is sublimated.
o High vapor pressure
o Low melting point
o More volatile
 Residue – the solid particles that remained on the dish.
o Low vapor pressure
o High melting point
o Less or non-volatile
 Deposition – the process of changing gas to solid without passing through liquid state.

SUBLIMATE RESIDUE
Salicylic acid – sodium
Salicylic Acid Sodium sulfate
sulfate mixture
Physical Appearance Needle-like Powder-like
Polarity Non-polar Polar
Type of Compound Organic Inorganic
Colorless solution with Cloudy solution with white
Observation
salicylic acid crystals precipitate

 Salicylic acid + BaCl → no reaction

o Salicylic acid is an organic compound, while barium chloride is an inorganic
compound.
 Na2SO4 + BaCl → NaCl + BaSO4↓
o Sodium sulfate is a polar inorganic compound that results to white precipitate
(barium sulfate) when added with barium chloride.
 EXERCISE 5

Separation and Purification of Organic Compounds

DISTILLATION

 Distillation is usually employed for the purification of liquid organic substances.

 It involves evaporation and condensation.
o Evaporation – the conversion of liquid to vapor state with the aid of heat
o Condensation – the process in which vapor turns to liquid by cooling.
 Distillate – the liquid that passed through the distilling flask.
 It requires a distillation flask fitted with a thermometer and a water-cooled condenser.
 Boiling chips are also used to prevent bumping by producing a constant steam of bubbles
which keeps the liquid in motion.

 Boiling point is one of the most important criteria of purity, as it is constant in every pure
organic substance at a definite pressure.
 Distillation could be used to convert muddy water to potable water.
o Solid particles should be allowed to settle and then decanted. Then, the water
should be heated to boil in low to moderate fire. It should be below the boiling
point of water. This would rid the water of impurities.
 The use of distillation is limited to a certain extent because some organic compounds
decompose when an attempt is made to distill them at normal atmospheric pressure.
Common Types of Distillation
1. Simple Distillation – used to separate a volatile liquid from a non-volatile solute.
– a large temperature difference (more than 20°) between the boiling
points of the component is necessary to obtain efficient separation.
– the component which is more volatile will distill over first, in almost
pure form at a definite constant temperature, the second component will
distill over when the boiling point again remains constant for a long period
of time.

2. Fractional Distillation – the process of collecting separate fractions according to arbitrary

boiling point ranges during the distillation of a mixture of substances.
– It is performed readily by means of a special fractioning column.
– It cannot be used if the components of a mixture have boiling points
very close together because some substances form a “constant boiling
mixture”, also known as azeotropic mixture.
 Azeotropic mixture – a mixture of liquids of certain definite
composition that distills at constant temperature without change
in composition.

4. Diminished-Pressure Distillation

5. Steam Distillation

Thermometer
Volume of Distillate Ignition Test Sodium-Nitroprusside Test
Reading
56°C 5 mL Flammable Red-wine colored
Slightly
100°C 5 mL Lighter color
flammable

 Sodium-Nitroprusside Test – Clinical test for urine. Test for acetone.

EXERCISE 6

Separation and Purification of Organic Compounds

EXTRACTION OF CHLOROPHYLL

 Extraction, by the use of solvents, is a frequently used method of withdrawing or substance

from a mixture.
o It is usually performed using two immiscible solvents. The mixture is first
dissolved in one of the liquids and then shaken with the other to distribute the
components.
 Aside from extraction, it also involves decantation and filtration.
o Decantation – the process of separating solid-liquid components of mixtures by
gently pouring out the liquid so as not to disturb the solids that readily settle at
the bottom of the container.
o Filtration – the process of separating the solid from the liquid by using a
porous filter.
 Residue – the solid particles that remained on the filtering medium.
 Filtrate – the liquid that passed through the filtering medium.
 Water is usually one of the solvents used in the extraction process.
 The other liquid is usually a non-polar organic liquid.
o Diethyl ether – used extensively as an extracting solvent.
– organic solvent
– high solvent power for hydrocarbons and for oxygen-
containing compounds.
– Highly volatile. It boils at 34.60°C
– Fire hazard
o Ether – slightly soluble in water
– Its efficiency can be improved by the addition of a small
amount of ionizable salt, such as NaCl.
– The increase polar property of the water solution will cause a
decrease in the solubility of the organic solute.
 Salting-out effect – the reduced solubility in water in
the presence of an electrolyte.
o Petroleum ether
o Ligroin
o Benzene
o Carbon tetrachloride
o Chloroform
o Methylene chloride
o Ethylene dichloride
o N-butanol – slightly soluble in water
  Extraction of water-immiscible solvent is useful for isolation of natural products that occur
in animal and plant tissues that have high water content.

Extraction
It acts as an
Malunggay + sand agitator

grind
Has polar and non-polar
Non-polar end
+ hexane + methanol
Extracts chlorophyll of Water soluble
malunggay Absorbs water
decant
It also absorbs other non-
filter polar substances of
malunggay

crushed leaves and sand green solution

separatory funnel

dark green extract water-methanol solution

Absorbs traces of +
water anhydrous sodium sulfate

Non-polar
Chlorophyll
 EXERCISE 7

Separation and Purification of Organic Compounds

CHROMATOGRAPHY

 Chromatography - the process of separating the substances in a complex mixture by their

different affinities to the adsorbent.
 It is one of the most useful methods of separating the components of minute amount of
mixtures.
 It used for analyzing mixtures of colored chemicals.
 It was invented by a Russian botanist, Mikhail Semyonovich Tsvet, in 1901, while
researching on plant pigments.
 This technique involves separation of constituent elements of the mixture.
 Chromatography is derived from the Greek words, chroma meaning color, and graphein
meaning to write. Thus, the word chromatography literally means color writing.

 It has two phases:

o Stationary Phase – refers to the column packing material and is either solid or
liquid.
- It is usually a piece of high quality filter paper.
o Mobile Phase – represents a mobile phase of liquid or gas.
- The mobile phase is a developing solution that travels up the
stationary phase, carrying the samples with it.

 Components of the sample will separate readily according to how strongly they adsorb on
the stationary phase versus how readily they dissolve in the mobile phase.

Different Classification of Chromatographic Methods

1. Adsorption Chromatography (liquid-solid chromatography) – utilizes a mobile liquid or

gaseous phase that is adsorbed onto the surface of a stationary solid phase. The equilibration
between the mobile and stationary phase accounts for the separation of different solutes.

2. Partition Chromatography (liquid-liquid chromatography) – uses a thin film formed on

the surface of a solid support by a liquid stationary phase. Solute equilibrates between the
mobile phase and the stationary liquid.

3. Ion Exchange Chromatography – resin (the stationary solid phase) is used to covalently
attach anions or cations onto it. Solute ions of the opposite charge in the mobile liquid phase
are attracted to the resin by electrostatic forces.

4. Molecular Exclusion Chromatography (gel permeation chromatography) – liquid or

gaseous phase passes through a porous gel which separates the molecules according to its size.
The pores are normally small and exclude the larger solute molecules, but allow smaller
molecules to enter the gel, causing them to flow through a larger volume. This causes the larger
molecules to pass through the column at a faster rate than the smaller ones.

 Thin Layer Chromatography – it is usually used as an analytical technique rather than a

preparative method.
o The stationary phase used is an adsorbent in the form of a thin layer of an inert
solid on a supporting material, usually a think sheet of metal or plastic.
o The mobile phase is the solvent system used to separate the components of the
mixture. Hexane and/or ethyl acetate is commonly used.

 Paper Chromatography –a method used for testing the purity of compounds and
identifying substances.

Technique:
1. Introduce a small spot of the sample on the filter paper.
2. Put the filter paper into a container that has the mobile phase. Make sure the plate
touches the mobile phase.
3. The solvent moves up the plate due to capillary action and carries the sample upwards.
4. Remove the filter paper and allow it to dry
5. Spray it with ninhydrin to make the spots more visible.

 Ruhemann’s Purple - a purple coloration produced by ninhydrin in the presence of an

amino acid.

Calculation of Retention Factor (Rƒ)

Rƒ = distance traveled by the substance_
distance traveled by the solvent

Solvent front Distance traveled by the solvent = 5.2 cm

Distance traveled by the substance = 3.5 cm

5.2 cm

3.5 cm