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Group 2
Group 2
OBJECTIVES: To learn the different tests methods by which alkanes, alkenes and alkynes are
distinguished from each other
To identify the three hydrocarbons through their reactions
To understand the chemical reactions by which the hydrocarbons undergo
DISCUSSION:
Alkanes, alkenes, and alkynes are hydrocarbons containing hydrogen and carbon with differences in the
number of bonds between their carbons. An alkane is said to be saturated hydrocarbon because if does not
contain an unsaturated bond (a double or triple bond). Most alkanes are unreactive. An alkene have at least
one double bond while alkynes contain at least one triple bond. Unsaturation accounts for the different
reactions of these hydrocarbons. Within each hydrocarbon, physical and chemical properties vary
depending on the number of carbon atoms. For example, the greater the number of carbon atoms, the higher
is the boiling point of the hydrocarbon compared to one with less carbon atoms.
NOTE: Advanced reading on alkanes, alkenes and alkynes and MSDS of the chemicals.
FLAMMABILITY
PROCEDURE:
SOLUBILITY
PROCEDURE:
PROCEDURE:
PROCEDURE:
1. Place 1 ml of hexane in the test tube. Add 5 drops of 5% Bromine solution dissolved in methylene
chloride.
2. Shake the mixture and observe what happens. Place a moist blue litmus paper above the test tube. Note
if there is any change in the color of the blue litmus paper. Most alkenes react readily with bromine in
the dark and at room temperature while alkanes shows no appreciable reaction.
3. Note any particular color change. The disappearance of the brown bromine color during the reaction
indicates the formation of a vicinal dibromide (colorless).
4. Repeat this process using toluene, cyclohexene, and acetylene.
1. Fill a water trough with water. Fill six test tube with water as follows: test tube #1, #2, #3 completely
full of water, test tube #4 with 50% water, and test tube #5 with 25% water.
2. Weigh about 100 grams of calcium carbide, and place inside a round bottom flask.
3. Set up the apparatus as shown in the figure.
4. Place your thumb over the full test tube, invert it, and place the opening of the tube below the water
level of the beaker.
5. Remove your thumb, after the tube is in the water..
6. Gradually add water to the calcium carbide, and collect the gas immediately when it is generated.
7. When the tube is full of gas, and before removing the tube from the water, place a stopper into the
tube.
8. Repeat the collection of acetylene gas for the other tubes. Stopper these tubes as well.
9. Test tee acetylene (test tube #1, #4, #5) by carefully bringing a lighted match.
FLAMMABILITY
CHEMICALS FORMULA OBSERVATION
HEPTANE C7H16 Flammable
CYCLOHEXANE C7H12 Flammable
TOLUENE C7H8 Flammable
Flammable, produced lesser soot than 25 %
100 %
full
Average flammability, produce more soot
ACETYLENE C2H2 75 %
than 50% full
50% Most flammable, produced least soot
25% Least flammable, produced most soot
SOLUBILITY
CHEMICAL FORMULA OBSERVATION
HEPTANE C7H16 Insoluble
CYCLOHEXANE C7H12 Insoluble
TOLUENE C7H8 Insoluble
FRACTIONAL DISTILLATION
DISCUSSION:
Azeotropes are a mixture of liquids that distills at a constant temperature without changing composition.
The best-known azeotrope is 95.5% ethanol and 4.5% water. Mixtures of liquids whose boiling points are
similar (separated by less than 70°C) cannot be separated by a single simple distillation. In these situations,
a fractional distillation is used. When a pure liquid undergoes distillation, the vapor composition is the
same as that of the liquid composition. The composition of the vapor is made up only of the lower – boiling
point or more volatile component of the liquid mixture, thus this vapor A condenses and collected as pure
component A.
An ideal solution of two liquids in a solution with less than 25°C difference in their boiling points are
separated by fractional distillation. The composition of the vapor differs from the composition of the liquid.
This is governed by Raoult’s Law which states that the vapor pressure of an ideal solution is dependent on
the vapor pressure of each chemical component and the mole fraction of the component present in the
solution or mathematically:
In a fractionating column, many distillations are occurring simultaneously, with the less volatile fraction
constantly condensing and returning towards the distilling flask while the more volatile fraction
continuously vaporized moving up the fractionating column and condenses. The use of a fractionating
column usually filled or packed with a suitable material such as stainless steel sponge or glass beads allows
a liquid mixture to undergo many vaporization condensation cycles as the material moves up the column.
With each cycle within the column, the composition of the vapor is progressively enriched in the more
volatile component. The distillation must be carried out slowly to ensure that numerous vaporization -
condensation cycles occur to obtain as pure product as possible.
PROCEDURE:
1. Place 25 ml each of toluene and benzene in the round – bottom flask. Add boiling chips to the mixture
to prevent over heating.
2. Set – up the apparatus as shown in Figure 1.
3. Heat the mixture with a small flame. Keep the collecting flask away from the open flame.
4. Collect fractions of distillate in several Erlenmeyer flask at different temperature ranges [75°C - 81°C],
[82° C - 88 °C], [89 ° C – 98 °C], [99° C - 105°C].
5. Turn off the burner when the temperature reaches 105°C and collect any additional distillate in another
flask.
6. Record the volumes of distillate collected at each temperature range.
7. Add the residue from the round – bottom flask to that of the last collected distillate.
8. Cool the apparatus then prepare to do a second distillation.
9. Replace the round bottom flask with another 100 ml round bottom flask. Pour all of the contents from
the first fraction to the flask [75°C - 81°C]. Connect the Liebig condenser and start the distillation.
10. Collect fractions of distillate that boils from 75°C - 81°C into another container. Turn off the burner
and measure the volume collected.
11. Cool the distilling flask then add the second fraction [82° C - 88 °C] to the distilling flask. Start the
distillation and collect fractions of distillate that boils from 75°C - 81°C into the first bottle. When the
temperature reaches 82°C, change the receiver for the fraction [82° C - 88 °C]. Turn off the burner
when the temperature reaches 89°C. Measure the volume collected.
12. Cool the distilling flask then add the third fraction [89° C - 98 °C] to the distilling flask. Start the
distillation and collect fractions of distillate that boils from 75°C - 81°C into the first bottle. When the
temperature reaches 82°C, change the receiver for the fraction [82° C - 88 °C]. When the temperature
reaches 89°C, change the receiver for the fraction [89° C - 98 °C]. Turn off the burner when the
temperature reaches 99°C. Measure the volumes collected.
13. Cool the distilling flask then add the fourth fraction [99° C - 105 °C] to the distilling flask. Start the
distillation and collect fractions of distillate that boils from 75°C - 81°C into the first bottle. When the
temperature reaches 82°C, change the receiver for the fraction [82° C - 88 °C]. When the temperature
reaches 89°C, change the receiver for the fraction [89°C - 98°C]. ]. When the temperature reaches
99°C, change the receiver for the fraction [99°C - 105°C]. Turn off the burner when the temperature
reaches 106 °C and measure the volumes collected.
14. Cool the distilling flask and remove the fractionating column and distill the residue in an ordinary
distilling flask. Collect the fraction [106°C - 111°C] that boils at 111 °C (toluene) and measure the
volume collected.
15. Submit the first fraction and the last fraction to your instructor while placing all other fractions in a
bottle supplied by your instructor.
Temperature Range 75°C - 81°C 82° C - 88 °C 89°C - 98°C 99°C - 105°C RESIDUE
QUESTIONS:
1. Define what is an azeotrope and what is the difference in its boiling point compared to the boiling
point of its individual component.
Azeotrope is a mixture of liquids that has a constant boiling point because the vapour has the
same composition as the liquid mixture. The boiling point of an azeotropic mixture may be
higher or lower than that of any of its components
2. What is the difference in using an ordinary condenser to that of using a Liebig condenser and how does
this affects the result of the distillation?
3. What is the importance of performing fractional distillation slowly?
If heat is supplied to the distillation flask too rapidly, the ability to separate two liquids by
fractional distillation may be drastically reduced.
4. Calculate the vapor pressure of a mixture containing 20 g of benzene and 20g of toluene at 30°C.
5. Compound A has a molar mass of 200 and boiling point range of 90°C. Compound B has a molar mass
of 100 and a boiling point of 90 °C. A and B are miscible liquids. What is the vapor pressure of a
mixture containing 200 g of A and 100 g of B at 90°C? What is the vapor pressure of a mixture
containing 100 g of A and 100g of B?
6. Given: CCl4 at 80°C has a vapor pressure of 847 mmHg. Toluene (C6H5CH3) at 80°C has a vapor
pressure of 288 mmHg. What will be the mole fraction of CCl4 in a mixture of CCl4 and toluene
which boils at 80°C? What would be the mass of toluene per gram of CCl4 in the mixture which boils
at 80°C?
Experiment No. 8
PROCEDURE:
1. SOLUBILITY IN WATER
2. FLAMMABILITY
This test may be used only with alcohols which are soluble in water. Mix 5 drops
of the unknown with 3 ml of the Lucas reagent. Tertiary alcohols react often within a few
seconds; the clear solution becomes cloudy and the tertiary chloride forms a later above
the reagent. Most secondary alcohols react within 10-15 minutes. Primary alcohols may
require 30 minutes or more.
1. Solubility
Observations
Tert-butyl alcohol Partially soluble
Isopropyl alcohol Soluble
Ethanol Soluble
N-amyl alcohol Insoluble
2. Flammability
Observations
Tert-butyl alcohol Yellow flame
Isopropyl alcohol Yellow and blue flame
Ethanol Blue flame
3. Lucas Test
Observations
Tert-butyl alcohol Cloudy solution is observed and formation of
precipitate occur
Isopropyl alcohol Formation of tiny precipitates
Ethanol Formation of precipitate after some time
CHROMATOGRAPHY
DISCUSSION:
In chromatographic separations, the compounds dissolved in a sample (solid, liquid or gas matrix) are made
to pass through a stationary phase such adsorbing material as silica gel or polymer beads. If the mixture has
several components, the components move over the stationary phase at different speeds depending on
several factors including varying molecular affinity or attraction of the components towards the stationary
phase. As a consequence the components retained at different extents and are separated.
There are several methods of chromatographic separations. In Column Chromatography, upright columns
are usually employed to hold the stationary phase, packed particulate matter. The mobile phase containing
the mixture of components can either be a liquid or gas. The solvent that drives the component through the
column is known as the eluent. In gas chromatography, the carrier is a gas. In Paper Chromatography, a
spot of the solvent – solute mixture is placed on filter paper. The filter paper is dipped and suspended in a
suitable liquid. The solvent rises on the paper by capillary action and as it passes over the spot, the
components of the colored spot separates at different rates. In Thin – layer Chromatography, a glass plate
coated with a thin layer of adsorbent is used instead of paper. The plate is spotted with the sample and then
dipped into a solvent that rises through the plate by surface tension enabling separation of the components.
In paper and thin – layer chromatography, Rf is known as the retention factor. The values are obtained
mathematically from the following equation:
The Rf values are obtained from the chromatograms by measuring the distances from the starting point of
the spot to the estimated point of maximum density of each moving color. The distance traveled by the
solvent can be determined by measuring the distance the solvent has traveled in the stationary phase.
PROCEDURE:
PAPER CHROMATOGRAPHY
1. Cut a smooth filter paper into a rectangle with dimensions of 10 cm x 20 cm. Draw a pencil line about
a cm from one end of the strip. This should be parallel to the width of the rectangular filter paper. This
is the starting point for the dyes solution.
2. Place a drop of 10 different dyes and dye solutions with spacing of 2 cm each (Consult the table for the
dyes used). Let the spots dry for at least 5 minutes.
3. Form the paper into a roll with the spots at the bottom and stapled the sides together but without the
sides overlapping.
4. Place the roll (colored spots at the bottom) in a 600 - ml beaker saturated with 5 ml of 1:1 ethanol and
water. Cover the beaker with a watch glass, let stand and allow the solvent and spots to travel up the
filter paper. When the solvent has reached within 5 millimeters the top of the filter paper , remove the
paper and marked the highest point the solvent has reached.
5. Let the paper dry. Start measuring the distances in the filter paper. Calculate the R f values of the dyes
and the dye solution.
NOTE: Knowledge of the MSDS of chemicals used and advanced reading of the topics are required.
Methyl red Methyl red Methyl Methylene Methylene Methylene Eriochro Eriochrom
+ Methyl Orange blue + blue blue + me black e black +
Rf values (computed) Orange Methyl Eriochrome Eosine
Orange black
0.7059 0.5882 0.2353 0.1412 0.2941 0.5059
0.6824 0.2 0.0470 0.7059
Computation:
Methyl red:
Methyl orange:
Methylene blue:
Eriochrome Black :
QUESTIONS: