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Lab Manual
Lab Manual
(4-hydroxy-3-methoxybenzaldehyde)
Purpose:
To purify the vanillin by recrystallization procedure and to determine the recovery percentage.
The purified vanillin samples will be evaluate through melting point on the next experiment.
Introduction:
Recrystallization is a technique utilizes the observation that the solubility of solids in liquids
usually increases dramatically as the solvent temperature is increased. A barely saturated
solution of the solid in the hot solvent is prepared and allowed to cool. The solubility
decreases as the temperature drops. Solid crystallizes back out upon cooling. These impurities
pass through the final cold filtration. Several steps are followed in a typical recrystallization.
A. Solvent selection ~ The solubility of the solid is tested in possible solvents until
desirable solvent properties are found (solid should have low solubility in the cold
solvent and high solubility in the hot solvent).
B. Dissolving of solid ~ The solid is dissolved in a minimum amount of hot (usually
boiling) solvent to prepare a saturated solution.
C. Hot filtration ~ If insoluble impurities are present (not in todays experiment) a hot
gravity filtration is preformed to collect the impurities.
D. Solution cooling ~ The solution is allowed to cool and solidification should occur.
Sometimes seeding, scratching or cooling in an ice bath is necessary to induce
crystallization.
E. Ice bath cooling ~ The solution is usually cooled with an ice bath to further decrease
the solubility of solid in the solvent.
F. Vacuum filtration ~ A Buchner funnel, a filter flask, and as aspirator are used to
collect the solid.
G. Washing the crystals ~ While the crystals are still in the Buchner funnel, they are
usually washed with ice-cold solvent.
H. Drying ~ The crystals are usually air dried to allow evaporation of solvent
I. Percent recovery ~ The mass of the recrystallized sample divided by the mass of the
starting solid times 100% is the % recovery.
J. Purity determination ~ The purity of the sample is usually determined by a simple
physical measurement such as melting point.
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Procedure
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Vacuum filtration assembly. The filter flask is clamped and test tube is
inserted to collect the filtrate
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EXPERIMENT 2 MELTING POINT DETERMINATION
Purpose
Introduction:
In previous experiment, the attempted were made to purify a sample of vanillin. Today you
will determine the melting point measurement, the success of the purification. Anytime a
compound is obtained from a natural or synthetic source, its identity must be determined and
or verified. Physical properties such as density and melting point are extremely useful for
verification purposes because they involve quick and accurate procedures. These properties
also provide a simple method of obtaining a rough indication of purity. At 5 C difference
between an experimental and an expected melting point for example, indicates that the sample
is approximately 95% pure. Each 1% (up to about 10%), very roughly, depresses the melting
point 1C. impurities not only depress melting point but broaden them. Thus, if compound A
is supposed to melt at 65 C but experimentally it is found that heating causes it to begin
softening at 57 C and total liquefy at 65 C, we report that sample has melting range of 57
62 C and is considerably impure. The fact that contaminants tend to depress melting points
enables one to distinguish between two compounds with the same melting point.
Procedure
Using the procedure described below, determine the melting point of samples A, B and C
below. For the mixed sample, add approximately equal amounts of each compound to mortar
and grind them together with the pestle before inserting them into capillary tube.
1. Fill the capillary tube by pressing the open end onto the powdered sample until there is
about a 0.5 1 cm length of sample in the tube.
2. Now drop the capillary tube, sealed end down, through a 1 m piece of 6 mm glass tubing
that is being held on a hard surface.
3. The impact of capillary with the hard seldom results on breaking and causes the sample to
drop to the bottom of the tube.
4. Repeat the dropping procedure until the sample is packed in the bottom of the tube.
5. Place the capillary tube in the sample holder of the melting point apparatus.
6. Press ON button and observed the plateau light. When the plateau light is on, press the set
button until the heat light turn ON.
7. Start to record the melting point sample when the heat light is ON.
8. Observe the sample through magnifying eyepiece part.
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Results and Discussions
Melting Range C
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EXPERIMENT 3 REACTIONS OF ALKANE, ALKENE AND
CYCLOALKENE
Purpose:
Introduction:
Hydrocarbons are compounds containing only the elements hydrogen and carbon. The vast
number of hydrocarbons is indicative of the number of different ways the carbon skeleton can
be arranged. The major uses of hydrocarbons are as fuels and solvents. The properties, which
make them ideal for such, will be investigated. The bonding patterns vary with each
hydrocarbon family (alkane, alkene, alkyne, aromatic). The difference in chemical reactivity
will be studied. Saturated hydrocarbons contain only single C-C bonds, so-called sigma
bonds. Unsaturated compounds contain at least between two carbon atoms is the so-called pi
() bond. In general, -bonds are more one C=C or CC (double or triple) bond. The second
and third bond reactive than -bonds. In many cases, the -bond will react and the -bond
will remain unaffected. Two useful tests for unsaturation in laboratory analysis are the
reaction with bromine and the reaction with potassium permanganate.
Test with Br2: The -bond of an alkene is extremely reactive toward addition of bromine. The
red color of Br2will disappear almost immediately in the presence of a C=C. In time many
alkanes and aromatic hydrocarbons will also decolorize bromine by a substitution reaction.
The time factor is important to distinguish the addition reaction of an alkene from a
substitution reaction.
Test with KMnO4(Baeyer Test): The -bond is also reactive toward the strong oxidizing
agent KMnO4. The purple color of KMnO4will disappear as it is reduced. Under neutral or
basic conditions a brown precipitate (MnO2) will be observed. Under acidic conditions the
colorless Mn+2is produced. In all cases, though, the purple color of the permanganate ion.
Procedure:
Each student will be assigned an unknown. As you are performing the classification tests on
known compounds, test the unknown also. At the end of the period you should be able to
identify the unknown.
Test the following for combustibility: Natural gas (predominantly methane), heptane, 2-
pentene, toluene, and cyclohexane. Toluene is the common name of methylbenzene which is
an aromatic compound. Because it is aromatic, you will observe properties unlike unsaturated
compounds.
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1. Natural gas: Ignite your burner. Observe the flame.
2. Liquids: Place 1-2 drops (no more) on the end of the scapula. Carefully ignite it in the
Bunsen flame and immediately remove it from the burner. Observe the results. Note the
quickness of the reaction, the type of flame, and the residue (if any).
1. Place 10 drops of the hydrocarbon in the smallest test tube. Add 2 mL water, stopper and
shake. If there is only one layer, the hydrocarbon has dissolved in the water. If there are
two layers, the hydrocarbon has not dissolved. In some cases the hydrocarbon is lighter
than water, sometimes heavier. Note the relative densities.
2. Place 10 drops of the hydrocarbon in a small test tube. This time add 2 mL of
cyclohexane. Stopper, shake and observe.
3. Repeat Steps 1 and 2 for each hydrocarbon. Record results.
4. Dispose of waste in the proper containers. Organic solvents do NOT go down the sink.
1. Prepare a blank solution from 2 mL acetone in a test tube and adding two drops of purple
KMnO4solution. No reaction should occur. The color may be used for comparison with
the other hydrocarbons.
2. Prepare each sample test tubes as follows: 2 mL acetone (solvent), 4 drops of the liquid to
be tested, and 1-2 drops (not more) of KMnO4 solution. The result is evident after 5
minutes.
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Results and Discussions
Record miscible as +, immiscible as , note if density is> or less < than solvent (if less
dense the sample floats on the solvent)
Compound
Solubility in water Solubility in Cyclohexane
Miscible or Relative Miscible or Relative
immiscible density immiscible density
Heptane
2-Pentene
Toluene
Cyclohexane XXX XXX
Unknown
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Compound Reaction with Br2 Reaction with KMnO4
Heptane
2-Pentene
Toluene
Cyclohexane
Cyclohexene
Unknown
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EXPERIMENT 4 COMPARING THE REACTION OF ALIPHATIC AND
AROMATIC HYDROCARBON
Purpose
Introduction
Hydrocarbons, compounds that contain only carbon and hydrogen, can be classified into
several types, depending on their structure. Aliphatic hydrocarbons are divided into three
classes: alkanes have only single bonds, and are said to be saturated; alkenes and alkynes
have carbon-carbon double or triple bonds, and are said to be unsaturated. Aromatic
hydrocarbons are cyclic compounds whose structure is related to that of benzene, with six -
electrons in a six-member ring.
The following experiments illustrate some of the fundamental reactions of saturated,
unsaturated, and aromatic hydrocarbons. The three classes sometimes react differently toward
the same reagent, in which case it may be used to distinguish between them.
Procedure
Aliphatic Hydrocarbon
Bromine or 1. Put 1 mL portions of cyclohexane into two separate test
chlorine water tubes.
2. Add 10-15 drops of bromine or chlorine water.
3. After shaking the tubes, place one in the dark, (under the
counter) and expose the other to sunlight or a bright light for
a few minutes.
4. Then compare the colour of the two tubes. Test for the
presence of hydrogen bromide or hydrogen chloride by
holding a piece of moist blue litmus at the mouth of each
tube.
5. Add 1 mL of cyclohexene to a clean test tube.
6. Add 10-15 drops of bromine or chloride water, shake the tube
and observe the result.
7. Test for the presence of hydrogen bromide or hydrogen
chloride evolution.
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3. Shake the tubes well for 1 -2 minutes, and note the results.
Aromatic Hydrocarbon
Bromine 1. Add 1 mL of toluene to a small test tube.
2. To another, add a few iron filings, followed by 1 mL of
toluene, using the latter to rinse down any filings stuck on the
test tube walls.
3. To each test tube add three drops of bromine.
4. Place the tubes in a beaker of warm water for 15 minutes.
Observe the colour of each tube, and whether or not
hydrogen bromide was evolved and record the results.
Describe the color changes you observed and then conclude reactions or no reaction.
Compound Reaction with Reaction with Reaction with Balanced
Br2 KMnO4 Sulphuric Acid Equation
Heptane
2-Pentene
Cyclohexane
Toluene
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EXPERIMENT 5 SIMPLE DISTILATION
Purpose:
Introduction
Distillation is an experimental laboratory technique that is used to separate and purify liquid
organic compounds. For most practical purposes, distillation is an effective technique to
purify a compound from contaminants, as long as that compound is the major component
(>95%)of the mixture.
The distillation process can be explained in simple terms. When a compound in the distilling
flask is heated to its boiling point temperature, a phase change from the liquid state to the gas
state is induced. The compound, in the gas phase, moves out of the distilling flask up into the
other parts of the distilling apparatus. When the gas vapors encounter the cold condenser tube
(below the boiling point temperature) of the distilling apparatus, the gaseous compound
reverts back to the liquid phase and drips into the collection flask.
One might assume that distillation of a 50:50 mixture of two components, say ethanol (bp 78
C) and water (bp 100 C), would follow a similar phenomenon, where the ethanol would
distill off first at 78 C, and the water would distill at100C. However, this is not what is
observed. The H-bonding interactions between the ethanol molecules and the water molecules
prevent a "clean" distillation from occurring. Instead, what occurs is the formation of an
azeotrope, a mixture of the compounds that co-distills in a specific molar ratio at a
temperature different from the boiling point of either of the individual components.
However, mixtures concentrated in one component can be achieved using this technique.
Consider commercial mouthwash, the ethanol-water mixture that will be used in this
experiment. Heating commercial mouthwash to ~78C will result in an azeotrope that has an
ethanol-water molar ratio of 95%:5%. A distillate collected at or around this temperature, will
contain mostly (95%) ethanol.
Procedure
1. Ethanol will be distilled from 20ml of a commercial mouthwash using a simple distillation
apparatus, depicted in Figure below.
2. There is also a simple distillation apparatus set-up in the laboratory for you to examine.
3. Set up a stirrer/hot plate and ring stand in the hood. Place a 50 mL heating mantle on the
stirrer.
4. Insert a 50mL round bottom flask (distilling flask) into the heating mantle and clamp the
neck of the flask to the ring stand.
5. Be sure to position the flask over the center of the stirrer plate.
6. Measure out exactly 20 ml of commercial mouthwash using an Eppendorf pipet and weigh
it. Record the weight.
7. Dispense the mouthwash into the distilling flask.
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8. Add a magnetic stir bar to the flask and continue to set up the simple distillation apparatus
as shown in Figure below.
9. Attach a distilling head, thermometer adapter and thermometer.
10. Position the thermometer bulb just below the Y of the distilling head.
11. Place a second clamp on the apparatus at the joint between the distilling head and the
thermometer adapter.
12. (Never clamp anywhere except at the joints! It will crack the glassware.) Set up a second
ring stand.
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22. Monitor the thermometer temperature as the distillate drips into the collection flask.
Distillate should be collected when the thermometer reads 77-79C (calibrated and
corrected). (This is actually a ~95% ethanol-5% water azeotrope.).
23. When the temperature rises above 79C, turn the Variac off, remove the collection flask
and replace it with a second, clean flask.
24. Weigh a clean, dry 50 ml beaker and record the weight. Dispense the collected distillate
into the pre-weighed beaker and weigh it again to determine the weight of the distillate.
1. Calculate the percent recovery of ethanol from the total volume of mouthwash you
distilled. Show your calculations below.
2. What brand of mouthwash did your group distill? Using the table below, list your %
recovery of ethanol and the percent recoveries of ethanol others at your bench obtained
from the distillation of mouthwash. What is the average percent recovery?
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EXPERIMENT 6 REACTION OF ALKYL HALIDES
Purpose
To observe qualitatively how factors such as electrophile structure, solvent and concentration
influence the rate of nucleophilic substitution.
Introduction
Nucleophilic substitution reactions constitute a very important class of organic process. In a
very general sense, these reaction involve:
A nucleophilic: an electron-rich species that forms a new bond to an electron-deficient
carbon atom in a molecule;
An electrophile: an electron-poor species that is attacked by the nucleophile and expels the
leaving group;
Leaving group: the ion or molecule that is displaced from the electron-deficient carbon of
electrophile by nucleophile.
There are two limiting mechanisms for nucleophilic substitution reaction; SN1 (first-order), in
which the leaving group departs prior to nucleophilic attack (often by the solvent; hence, this
process is sometimes called solvolysis), and SN2 (second order), where approach by the
nucleophile occurs at the same time as the leaving group is departing. These reactions are
highly dependent on the precise reaction conditions, as discussed in detail in your textbook.
Procedure
General Procedure
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1. Each test must be performed in a clean test-tube. If you rinsed out your test tube with
water, make sure that you rinse with ~0.25 mL of the solvent (ethanol or acetone) used in
the next test.
2. Do not contaminate reagents with samples or other reagents. Each reagent is provided
with a pipette, which should only be used with this specific reagent.
3. Perform tests on each of the alkyl halides provided;
1-chlorobutane,
1-bromobutane,
2-bromobutane,
t-butyl chloride,
crotyl chloride; (E)-1-chloro-2-butene
4. Examine the results to make sure that they make sense (for example, a 3 o alkyl halide
should not react via an SN2 mechanism faster than a 1 o alkyl halide).
5. Repeat tests if you are uncertain about the outcome.
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3. Record your observations.
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EXPERIMENT 7 PREPARATION OF CYCLOHEXENE
Purpose
Introduction
Procedure
1. Set up a fractional distillation apparatus (see Experiment 5), using 100 mL round-
bottomed flask as the distilling flask and a 25 mL round-bottomed flask as the receiving
flask. Do not pack the fractionating column. Keep the receiving flask in an ice-water bath
to reduce evaporation.
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5. Gravity filter the solution into a dry 50 mL round bottomed flask, and set up for a simple
distillation using dry glassware. Remember that the connecting adaptor, adaptor outlet and
condenser (used in sep 1) might contain droplets of water that have to be removed (by
washing with acetone) in order to obtain dry cyclohexene. The dark residue in the
distilling flask can be removed using milliliter of methylene chloride and a test tube brush.
6. Collect the fraction that boils in the range of 80-85 C in a pre weighed vial or test tube
that is immersed in an ice-water bath. Calculate the percent yield.
7. Perform the following test for unsaturation:
a. Add 5-10 drops of distilled cyclohexene to 0.5 mL of a 1% potassium permanganate
solution in a test tube.
b. Add 5-10 drops of distillate to 0.5 mL of 1% bromine water solution in a test tube.
8. Observe and record the results of these two tests, then compare them with the results
obtained when cyclohexane is used instead of cyclohexene.
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