ORGANIC

CHEMISTRY

Post laboratory Activities 1 - 5

BRIEF HISTORY

 Late 18th century:

• Compounds from living organisms - Organic
• Compounds from lifeless matter – Inorganic
• Organic compounds thought to have ‘vital force’
Ammonium cyanate Urea
(from mineral sources) (from
urine)
‘Inorganic’ ‘Organic’
DISPROVED THEORY

 Wöhler 1828
D
Ammonium Cyanate Urea
(Heat)

•Discredited concept of
‘vital force’
 Experiment # 1
Organic
And
Inorganic Compounds
 ORGANIC AND INORGANIC COMPOUNDS
A. SOLUBILITY – the quality condition of being dissolved

Water Ethanol ether

Benzoic acid Insoluble Soluble Soluble
Sodium Soluble Insoluble insoluble
chloride
Calcium Sl. Sol. Insoluble Insoluble
carbonate
Urea Sl. Sol. Soluble Soluble

In what type of compound is benzoic acid soluble?

Organic solvents/non polar

In what type of compound is sodium chloride soluble?

Inorganic solvents/polar
Conclusion:

“Organic compounds are soluble in organic/non polar

solvents while inorganic compounds are soluble in inorganic
solvents/polar solvents”

The principle “like dissolves like”

B. MELTING POINTS AND BOLING POINTS

Boiling Point – temperature at which a liquid boils

- temperature at which a vapor pressure of
liquid is equal to the atmospheric pressure that turns
liquid to its gaseous state.

Melting Point - temperature at which a solid melts or

fuses
Which of the two compounds melted first?

Benzoic acid

Which of the three liquids boil first, second and last?

1st – ether
2nd - ETOH
3rd – H2O

Conclusion:

Organic compounds have low melting

and boiling point.
Inorganic compounds have a higher
melting and boiling point.
C. STABILITY TOWARDS HEAT

After heating the table salt in a clean dry test tube in 2 minutes,
then cooling it down…
NO CHANGE

After heating a pinch of cane sugar..

It melted and turned to black
After heating benzoic acid…
 it melted

Conclusion:

Organic compounds are less stable towards heat than

any inorganic compounds

Organic compounds which behave like sugar and benzoic acid

when heated are…
D. COMBUSTIBILITY - is a measure of how easily a substance will set on fire, through fire
or combustion.
Is ethyl alcohol combustible? YES

Is ether combustible? YES

Is the result the same if water was use instead of alcohol? NO

If we use carbon tetrachloride is it also combustible NO

Conclusion: Organic compounds undergo combustion readily accepts

organic halides
E. IONIZATION - Formation of ions in a solution

1mL NaCl solution + 2 drops of AgNO3

= formation of white precipitate

1mL CCl4 + 2 drops of AgNO3
= formation of layer (no reaction)
 CnH2n+2 + O2 CO2 + H2O
(for complete combustion)

Let’s Apply:
Show the complete equation
for the ff. hydrocarbons
1.C6H14
2.C4H10
Conclusion:

Organic compounds do not undergo ionization

process while inorganic has high ionization
F. ACIDITY AND ALKALINITY
a. Dilute HCL – strong acid
b. Dilute acetic acid - weak acid
c. Dilute NH4OH – weak base
d. Aniline – weak base
Conclusion:
Organic compounds has lower degrees of
alkalinity and acidity
Where as inorganic compounds has high
acidity or alkalinity
DETECTION OF COMMON ELEMENTS
IN ORGANIC COMPOUNDS
A. TEST FOR CARBON, HYDROGEN AND OXYGEN

Result with limewater: white precipitate

Carbon dioxide

A) Cane sugar and cupric oxide

C12H22O11 + 24CuO 12CO2 + 11H2O + 24Cu

B) Limewater + the gas produced in (a)

Ca(OH)2 + CO2 CaCO3 + H2O

B. TEST FOR NITROGEN

NH2 – CO – NH2 + CaHNaO2 2NH3 + Na2CO3

NH3 + H2O NH4OH

C. TEST FOR HALOGENS

1.Beilstein Test
2. Silver Nitrate (AgNO3 )

Cl– + AgNO3 → AgCl + NO3–

White precipitate

D. TEST FOR SULFUR AND PHOSPHOROUS

Test for sulfate ion
BaCl2 + SO4-2 BaSO4 + 2Cl-
white precipitate
Test for Phosphate ion
PO4-3 +12 (NH4)2MoO4 + (NH4)3PO4●12MoO3 + 21 NH4NO3
21 HNO3 + 12 H2O
( Ammonium molybdate) ( Ammonium phosphomolybdate)
Answers to Questions:
1. What is the purpose of soda lime?

2. Write the systematic identification of organic compounds.

Laboratory set-up for gravity filtration:

A physical method that

separates a solid from a
liquid through the use of a
porous material such as a
filter paper
Experimental observations:
A.
1) The residue resembles physical descriptions
similar to benzoic acid. Benzoic acid is
insoluble in water; sugar is infinitely soluble in
water.
2) The residue resembles the crystalline
properties of sugar. Benzoic acid is soluble in
denatured alcohol; sugar is insoluble in
denatured alcohol
B.
1) The residue contains crystals of both benzoic
acid and urea. Benzoic acid and urea are both
insoluble in water.
2) No residues were found on the filter paper.
Benzoic acid and urea are soluble in
denatured alcohol.
QUESTIONS
1) Selective solubility is a separation technique to
remove a component of a mixture. One of the
components is highly soluble in the medium (or
solvent); whereas the other component(s) are
insoluble. In such a way, the compound
requested can be removed and purified.
QUESTIONS

2) Sugar in part A.1 can be recovered by

evaporation and recrystallization.
3) Solvents available for use in the purification of
organic compounds:
 Ether; benzene; chloroform; cyclohexane;
acetone; ethyl acetate, etc...
Simple laboratory set-up for sublimation:
PURPOSE

 What’s the ultimate purpose of sublimation?

 Sublimation, which involves heating the
compound at low pressure from one apparatus
and condensing it in another, is used to purify a
compound.
Experimental results:
Describe the appearance of the material remaining
in the bottom of the beaker.
Caramelized sugar with small white crystals
remained at the bottom of the beaker.

How does it compare with the material which was

sublimed?
The sublimate formed were pure white crystals
which adhered on the bottom part of the flask
and at the walls of the beaker.
 Questions
1. Sublimation- transition from solid to gas phase with no
intermediate liquid stage.
2. Limitations of sublimation:
- Not as selective as crystallization; typically requires a
vacuum & usually requires that the compound you are
trying to separate is volatile while the others are not
volatile
- Small yield
- The VP of the substance must be different from the VP of
the impurities; otherwise, both substances will be
transported to the gas phase in almost equal amounts
thereby not achieving good purification
3) Explain how fractional sublimation may be applied to
a mixture of two substances which sublime closely
together.
 Requires temperature or vacuum control.
 Special concern must be taken to prevent the
solid from clogging the apparatus.
Experimental result:
After evaporation; white crystals residue:
(benzoic acid, C6H5COOH)
3. What is the major disadvantage of using ether as an
extracting solvent?
a) Ether is highly volatile.
b) the flammability of its vapors makes
explosions and fires ever-present dangers
unless proper precautions are observed.
4. Why should the stopper always be removed from a
separatory funnel whenever a liquid is being drained
through the stopcock?
So as to remove/release the pressure for
the smooth flow of the liquid
QUESTIONS

5) The distribution coefficient, KD (ether/water), between ether and water

for aspirin at room temperature is 3.5. (a) What weight of aspirin would be
extracted by a single extraction with 60 ml of water from a solution of 10
grams of aspirin in 100 ml of ether? (b) Calculate the weight of aspirin
which would be removed by three extractions with 20 ml portions of water.
Distribution Coefficient , KD = C2 / C 1
Where C2 and C1 are the concentrations at equilibrium in
mass/volume
a) 3.5 = (10 – x) / 100 ml
(x/60 ml)
X = 1.46 g
b) For 3 extractions: 1st extraction:
3.5 = (10 – x1) /100
(x1 / 20)
X1 = 0.54 g dissolved in water;
9.46 g dissolved in ether
For the 2nd extraction:
3.5 = (0.54 – x2)/ 100
(x2 / 20)
x2 = 0.03 g dissolved in water;
0.51 g dissolved in ether
For the 3rd extraction:
3.5 = (0.03 – x2)/ 100
(x2 /20)
x2 = 0.0016 g dissolved in water;
0.0283 g dissolved in ether
Total wt aspirin extracted
= 0.54 + 0.03 + 0.0016
= 0.5716 g
Description of Impure Crystals (10g) acetanilide,
C6H5CONH2: Dirty white/ grayish
After complete crystallization:
- beaker in room temp: crystals formed were
bigger in size; more lustrous
- beaker in iced water:
product formed was lumpy
white solid in appearance
QUESTIONS
1. Why is the washing of crystals on the filter paper not as
effective a process of purification as crystallization?
 Crystals dissolved in warm solvent, upon cooling some, will
remain dissolved in the solvent and may be lost due to transfer
from a container to another.
2. How do you account for the formation of crystals of different
sizes in slow and rapid crystallization process?
ANSWERS TO QUESTIONS
3. What properties should ideally be possessed by a
recrystallization solvent?
a. Purified compound must be very soluble in hot
solvent and almost insoluble in cold solvent
b. The solvent dissolves the impurities completely at
room temperature
c. It must not react with the substance to be purified
d. Cheap, nonflammable, and non-toxic
e. It should have a boiling point lower than the boiling
point of the solid to be purified
f. Volatile solvent (low boiling point) and easily removed
EXPERIMENT 5
DISTILLATION
TYPES OF DISTILLATION
 Simple distillation
 Fractional distillation
 Flask distillation
 Azeotropic distillation
 Batch distillation
 Steam distillation
 Vacuum distillation
 Continuous distillation
 TYPES OF DISTILLATION

 Simple distillation - used if impurities are not volatile and the

liquid compounds doesn’t decompose when boiled at
normal atmospheric pressure
LAB SET-UP FOR FRACTIONAL DISTILLATION
INDUSTRIAL FRACTIONAL DISTILLATION
FRACTIONAL COLUMN
AZEOTROPIC DISTILLATION
• A special type of distillation specifically
used for azeotropic mixtures.
• They can’t be distilled directly as their
liquid and vapor composition are the
same.
• Other components are added to create
new low boiling azeotrope, creating two
heterogeneous layers.
• This can be easily distilled.
• In the production of ethanol, to break
azeotrope of 96% ethanol and 4% water,
benzene is added.
2. A) To completely fill up the condenser
b) To avoid formation of air pockets
c) to allow cooling system of the process; thus allow
vapor to turn into liquid that runs down the condenser
and collected in the receiving flask.
QUESTIONS:

1.To completely bathe the mercury bulb with the

rising vapor in order to get accurate readings;
- to ensure that it records temperature of
the distilling vapor and not that of the mixture
of vapors
 3) Possible sources of loss:
a) inaccurate measurements
b) presence of impurities
c) leakages due to improper or loose connections
d) evaporation of liquids
 4) Boiling chips are used to regulate heat and prevent
irregular ebullition or bumping which leads to
overheating.
SIMPLE AND FRACTIONAL DISTILLATION