Department of Pure and Applied Chemistry

College of Arts and Sciences

Visayas State University

Post-Lab Discussions on
Exercises 5-9
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 Department of Pure and Applied Chemistry
College of Arts and Sciences
Visayas State University

Exercise 5
Recrystallization and Melting
Point Determination
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Recrystallization of Impure Benzoic acid
Steps for Recrystallization
1. Solvent Selection
• Guidelines in selecting the solvent for recrystallization

a) Desired compound should be soluble in hot solvent and insoluble in cold solvent (room

temperature)

b) Boiling point of solvent must be low enough so it can be easily removed from crystals

c) Boiling point of the solvent should be lower than the melting point of solid to purify

d) Should not react chemically with solid being purified

e) impurities are either soluble at all temps or insoluble at all temps

List of Solvents used for Recrystallization

Water:

a) 100°C- 5.63g/100 mL (soluble)

25°C- 0.377g/100 mL (insoluble)

b) Boiling Point = 100°C

c) Boiling Point (water) = 100°C

Melting Point (Benzoic acid) = 122.3°C

2. Container used

• Beaker or other glassware are not suitable for recrystallization because it has a very
large surface area which lowers your recovery

• Erlenmeyer flask is the right glassware to use

3. Adding boiling chips
• Adding boiling chips to the solution will reduced bumping of solution to the flask during
heating.

NOTE:

Bunsen burner is not advisable if solvent is flammable(organic solvent). Hot plate is used
instead.
4. Adding activated charcoal
• applicable if solution is colored. Add to hot solution (not boiling). At boiling it will produce
froth (small bubbles).

• add activated charcoal to hot solution→ boil the solution

5. Filter the solution
• Hot gravity filtration- is used to separate insoluble impurities from a hot solution.

- require fluted filter paper and careful attention to the procedure

to keep the apparatus warm

• Fluted filter paper allows

faster filtration
• Stemless funnel prevents
premature crystallization

Folded vs. Fluted Filter paper Stemless vs. Short stem funnel
6. Formation of crystals
• Cooling of the solution at room temperature is done.

• Rapid cooling (immersing the flask in ice bath) can also be done but not advisable. This
cooling process produce small crystals which results to high surface area. High surface
area, more contaminants can adsorbed to the crystals
7. Removal of solvent and impurities
• solvent and impurities will be removed by vacuum filtration which uses Buchner funnel.

Buchner funnel
8. Drying of Crystals
• can be done by air drying or oven drying

• oven drying – temperature must be below melting point of crystals

• oven drying – 80°C is below melting point of crystals (122°C)

Percent Recovery
Melting Point Determination
of Benzoic acid
Melting Point
• purity of benzoic acid can be determined by measuring its melting point

• the temperature at which the solid and liquid states of a substance are in equilibrium at

atmospheric pressure.

• A pure solid material melts sharply at specific temperature. Impurities found in the solid

will tend to change the melting point by causing it to "spread" out into larger range.

• Melting point of Pure Benzoic acid- 122.3°C

Melting Point Determination

Measure melting
Closing one end of Loading of sample
point using melting
capillary tube in capillary tube
point apparatus
Closing the capillary tube

Close off the capillary tube at one end to prevent your sample from falling out
Loading of sample in the capillary tube

a) Depositing sample into the open end of a capillary tube c) Dropping the sample through a long tube

b) Inverting and tapping the tube on the benchtop d) Correct height of sample in the tube
Measuring of melting point using melting point
apparatus

Observed the melting of benzoic acid in melting point apparatus.

Record the temperature which benzoic acid begins to melt. And
Digital Melting Point
Apparatus also record the temperature in which the benzoic acid melted
completely.
Guide Questions:
• Explain how the rate of crystal growth can affect the purity of a
recrystallized solution?
Guide Questions:
• Why is the final product from a recrystallization isolated by suction
filtration rather than gravity filtration?
Guide Questions:
• Why is fluted filter used for hot filtrations?
Guide Questions:
• What is wrong with using a narrow, long stem funnel in the filtration of a
hot solution in a recrystallization?
 Department of Pure and Applied Chemistry
College of Arts and Sciences
Visayas State University

Exercise 6
Volatility: Distillation and
Determination of Boiling
Point
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Volatility
• condition in which liquid turns into vapor easily.

• a substance is said to be volatile if it boils at a

low temperature, changing from the liquid to
the gas phase.

• evaporates easily: acetone > ethanol > water

• volatility: acetone > ethanol > water

✓ evaporates easily = more volatile
Vapor pressure
• The vapor pressure is the pressure exerted by a pure component at equilibrium, at any
temperature, when both liquid and vapor phases exist .

Low temperature, low High temperature, high

vapor pressure vapor pressure
Boiling Point
• (of a liquid) is the temperature at which the vapor pressure of liquid equals the pressure
of the atmosphere above the liquid.

• As the temperature increases so the vapor pressure increases.

• Volatile liquids have higher vapor pressures and therefore boils at a lower temperature.
Principle:
As temperature increases the molecules Volatile substances have low boiling points
gain sufficient kinetic energy in which and relatively weak intermolecular
interactions. Nonvolatile substances have
liquid turns into gas. The stronger the high boiling points and relatively strong
intermolecular interactions.
bond, the higher energy and temperature
we need to break that bond. So that
means that IMF (intermolecular forces) is
one factor that determine if the liquid is
easy to evaporate or not.
London dispersion<Dipole-dipole<Hydrogen bond
Volatile vs. Non-volatile Solvents

Non-volatile substance refers to a substance Volatile substance is one that evaporates or

that does not readily evaporate into a gas under sublimates at room temperature or below.
existing conditions. Non-volatile substances Volatile substances have higher vapor pressures
exhibit a low vapor pressure and a high boiling versus non-volatile substances at the same
point. temperature.
Distillation
• a technique used to purify liquids

• involves the process of evaporation of the liquid state to the vapor state and condensation
of vapors to the liquid state

Liquid Gas

• can be simple, fractional , steam, or vacuum distillation

Types of Distillation:
1. Simple Distillation- used to separate liquids boiling below 150°C at 1 atm from non-
volatile impurities.

2. Vacuum Distillation- used to separate liquids boiling above 150°C at 1 atm from non-
volatile impurities.

3. Fractional Distillation- used to separate liquids with boiling point difference of less
than 40°C from each other at 1 atm.

4. Steam Distillation- used to isolate oils and other liquids that are insoluble or slightly
soluble in water.
Comparison of Volatility by Rate of Evaporation

Ethyl
Acetone Methanol Water 1-butanol
acetate

Record the time in which the compound evaporates completely. Take note which compound
evaporates first and evaporates last.
Distillation of water from dissolved non-volatile
solids, Boiling Point Determination

Simple Distillation
• Boiling chips- to avoid bumping
• Tap water was distilled in the
process to separate pure water
from dissolved ions
• The thermometer should place
in the right location
Guide Questions:
• What does temperature of water obtained at the first drop and at the
last drop indicated?
Guide Questions:
• Arrange the following compounds in order of increasing boiling point:
pentane, octane, hexane, 2-methyl pentane. Offer an explanation for
your arrangement.
Guide Questions:
• Water boils at 100°C at sea level (p = 1 atm). Assuming you are out
camping up the peak f Mt. Pangasugan, will the boiling point of water
be higher? Lower? Or remains the same. Explain.
Guide Questions:
• Arrange the following compounds in order of decreasing volatility:
acetone, methanol, ethyl acetate, 1- butanol and water. Give the basis
for your arrangement.
 Department of Pure and Applied Chemistry
College of Arts and Sciences
Visayas State University

Exercise 7
Solubility Classification
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Solubility of Organic Compounds
• Solubility in which a chemical reaction is the driving force

• Solubility in which simple miscibility is the only mechanism involved

Organic compounds when insoluble in water
• NaOH, NaHCO₃ , HCl, and conc. H₂SO₄

✓ 5% NaOH- phenol and carboxylic acids

✓ 5% NaHCO₃- strong organic acids (carboxylic acids)

✓ 5% HCl- aliphatic amines (1°, 2° and 3° amines)

✓ Conc. H₂SO₄- alcohol, ketones, aldehydes, alkenes

2.5 M NaOH
• Solubility will be indicated by the formation of a homogeneous solution, a color change,
or the evolution of gas or heat. If soluble, then your unknown is behaving as an organic
acid. The most common organic acids are carboxylic acids and phenols.

• Carboxylic acids are usually considered stronger acids than phenols, but both of these
acids will react with NaOH (a strong base).
2.5 M NaOH
• Compounds that contain acidic or basic functional groups that are insoluble in water can
become soluble in an aqueous environment if they form an ionic species when treated
with an acid or a base. This is because the ionic form is much more polar.

Phenol Sodium phenolate Acetylsalicylic Sodium

acid Acetylsalicylate
“Soluble salts” “Soluble salts”
5% NaHCO₃
• Solubility will be indicated by the formation of a homogeneous solution, a color change,
or the evolution of gas or heat. If soluble, then it is a strong organic acid. If not, then it is
a weak organic acid, if it dissolves in NaOH.

• The most common weak organic acid are phenols. Typically, only a carboxylic acid will
react with NaHCO3.
5% NaHCO₃

• Carboxylic acids, but not phenols, are soluble in aqueous NaHCO3 solution:

Salicylic acid Sodium Salicylate

1.5 M HCl

• Solubility will be indicated by the formation of a homogeneous solution, a color change,

or the evolution of gas or heat. If your compound is HCl-soluble, then it is an organic
base.

• Amines are the most common organic base.

1.5 M HCl

• The solubility of amines in dilute aqueous acid similarly reflects the fact that they
are stronger bases than water, and are converted by protonation (i.e. reaction
with a proton) to the polar ammonium ion:
 Department of Pure and Applied Chemistry
College of Arts and Sciences
Visayas State University

Exercise 8
Hydrocarbons
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Hydrocarbons
a. Ignition Test
• Ignition test indicates the presence of unsaturation. Hydrocarbons
that contain a delocalized ring of pi which causes the formation of an
unburned carbon.
• Saturated Hydrocarbons (Alkanes)
- burn with no or little soot.

• Unsaturated Hydrocarbons (Alkenes, Alkynes,

Aromatic)
- burn with high soot.
b. Reaction with Bromine
Bromine solution is brown. In this test when bromine solution is
added to the unsaturated hydrocarbon the brown colour disappears
if the hydrocarbon is unsaturated. Bromine forms an addition product
with the unsaturated hydrocarbon.

Note: Decolourization of orange-red colour of bromine solution

indicates unsaturation.
b. Reaction with Bromine
b. Reaction with Bromine
c. Reaction with Cold Permanganate
• In this test the pink color potassium permanganate disappears when an alkaline

potassium permanganate is added to an unsaturated hydrocarbon. The

disappearance of pink color may take place with or without the formation of

brown precipitate of manganese oxide.

• Note: Decolourization of pink colour of KMnO4 indicates unsaturation.

c. Reaction with Cold Permanganate
c. Reaction with Cold Permanganate
c. Reaction with Cold Permanganate

• Ethyne or acetylene on reaction with cold KMnO4 adds 4 OH− to the

triple bond. It is oxidised first to form ethane-1,2-dial and further
oxidation will give oxalic acid.
d. Reaction with Ammoniacal Silver Nitrate

• Only terminal alkynes react with ammoniacal silver nitrate to give

white precipitate of silver acetylides.
Guide Questions:
• Which among hydrocarbons gives negative results in reaction with
bromine? Why?
Guide Questions:
• In reaction with cold dilute permanganate, which among test
samples give positive results? Show the chemical reaction.
 Department of Pure and Applied Chemistry
College of Arts and Sciences
Visayas State University

Exercise 9
Classification Test for
Functional Groups
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 Department of Pure and Applied Chemistry
College of Arts and Sciences
Visayas State University

Exercise 9a
Aromatic Hydrocarbons
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a. Test for Aromaticity (Nitration Test)

• Benzene reacts with concentrated nitric acid in the presence of concentrated

sulfuric acid to form nitrobenzene. This reaction is known as nitration of benzene.
a. Test for Aromaticity (Le Rosen Test)
• Le Rosen test is just like nitration but formaldehyde is used instead of
nitric acid.
a. Test for Aromaticity (Le Rosen Test)
• Visible result (Toluene): Cherry red solution with formation of red
precipitate.
b. Ignition Test
• Ignition test indicates the presence of unsaturation. Hydrocarbons
that contain a delocalized ring of pi which causes the formation of an
unburned carbon.
• Saturated Hydrocarbons (Alkanes)
- burn with no or little soot.

• Unsaturated Hydrocarbons (Alkenes, Alkynes,

Aromatic)
- burn with high soot.
c. Reaction with AlCl3/CHCl3

• Friedel-Crafts Alkylation refers to the replacement of an aromatic proton

with an alkyl group. This is done through an electrophilic attack on the
aromatic ring with the help of a carbocation. The Friedel-Crafts alkylation
reaction is a method of generating alkylbenzenes by using alkyl halides as
reactants.
 Department of Pure and Applied Chemistry
College of Arts and Sciences
Visayas State University

Exercise 9b
Alcohols and Phenols
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Alcohols
• General formula: R-OH
Alcohols (Reaction with Na metal)

• Alcohols react with sodium to form a salt. When alcohols react with
sodium, a salt will be formed plus hydrogen; bubbles of hydrogen gas will
be seen.
• Tertiary alcohols are more reactive than primary alcohols due to the higher
amount of alkyl groups in the compound
Alcohols (Lucas Test)
 Alcohols (Lucas Test)
Primary alcohols do not react readily at room temperature with the added Lucas reagent whereas
tertiary alcohols react immediately.

The observation of a change where the clear and colourless characteristic of the solution changes to a
turbid, cloudy, and hazy one implies that a chloroalkane has formed. This observation is a positive
indication for the Lucas test.

Primary, Secondary, and Tertiary alcohols react with the Lucas reagent to form the chloroalkane at
different rates. Tertiary alcohols react the fastest due to the fact that organic chloride has relatively
low solubility in the aqueous mixture.
Alcohols (Reaction with K2Cr2O7)
• Primary alcohols can be oxidized to form an aldehyde and further oxidation
will give carboxylic acid.
• Secondary alcohols are oxidized into ketones. Ketones do not undergo
further oxidation.
• Tertiary alcohols are resistant to oxidation by oxidising agents.
Phenols
• General formula: Ar-OH
Phenols (FeCl3 Test)

• Phenols react with FeCl3 to form a colored complex with the Fe3+
ion. The color varies from purple to orange depending on the
structure of the phenol tested. Alcohols do not form colored
complexes with iron ion.
Phenols (Bromine Water Test)

• If bromine water is added to a solution of phenol in water, the

bromine water is decolorized and a white precipitate is formed which
smells of antiseptic. The precipitate is 2,4,6-tribromophenol.
 Department of Pure and Applied Chemistry
College of Arts and Sciences
Visayas State University

Exercise 9c
Carbonyl Compounds
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Aldehydes and Ketones
a. 2,4-dinitrophenylhydrazine test

Aldehydes and ketones react with 2,4-dinitrophenylhydrazine reagent to form

yellow, orange, or reddish-orange precipitates, whereas alcohols do not react.
Formation of a precipitate therefore indicates the presence of an aldehyde or ketone.
Aldehydes and Ketones
a. 2,4-dinitrophenylhydrazine test

Aldehydes and ketones react with 2,4-dinitrophenylhydrazine reagent to form

yellow, orange, or reddish-orange precipitates, whereas alcohols do not react.
Formation of a precipitate therefore indicates the presence of an aldehyde or ketone.
Aldehydes and Ketones
b. Tollens’ test

Tollens’ test, also known as silver-mirror test, is a qualitative laboratory test used to
distinguish between an aldehyde and a ketone. It exploits the fact that aldehydes
are readily oxidized into carboxylic acid, whereas ketones are not.
Aldehydes and Ketones
b. Tollens’ test
Carboxylic acids and its Derivatives
a. Formation of esters

Esters are produced when carboxylic acids are heated with

alcohols in the presence of an acid catalyst. The catalyst is usually
concentrated sulfuric acid.
Carboxylic acids and its Derivatives
a. Formation of esters
Carboxylic acids and its Derivatives
b. Hydrolysis of acid derivatives

All derivatives hydrolysed with water to form the carboxylic acid