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Chm125 Lab Manual Okt 2022
Chm125 Lab Manual Okt 2022
FOR
Edited by
Rizana Yusof
Mohd Hafiz Yaakob
UiTM Perlis Arau Campus
CONTENTS
Laboratory Report 3
Cover Page 3
Marking Scheme of The Laboratory Report 3
Sections of The Laboratory Report 3
Format For References 4
Experiment 1 5
Heating by reflux and filtering using Buchner funnel
Experiment 2 9
Distillation technique and determine the boiling point of a liquid
Experiment 3 12
Extraction and drying of an aqueous solution
Experiment 4 15
Determination of melting points
Experiment 5 18
Reactions of hydrocarbons
Experiment 6 21
Reaction of alkyl halides
2
LABORATORY REPORT
All written reports must be your own individual work. A complete laboratory report should
contain the following sections:
1. COVER PAGE
• course name/code:
• experimental number and title:
• student’s name:
• matrix number:
• name of laboratory partner:
• date of experiment:
• date of report submission:
• lecturer’s name:
• marking scheme table
The following marking scheme table must be included at the cover of laboratoy report
Contains Allocated Given
mark % mark %
i. Objective 1
ii. Introduction and hypothesis 2
iii. Materials, Apparatus and Methodology 3
iv. Diagram 2
v. Result and data 4
vi. Calculation 4
vii. Discussion 4
viii. Questions 2
ix. Conclusion 1
x. References 1
xi. Format, quality, Spelling, Punctuation, Grammar 1
TOTAL 25
3
• Materials, apparatus and methodology: List of the material, chemicals and
apparatus that you used to perform the experiment. The procedure should be
written in passive form to describe the experiment in detail. This should not be
a copy of the laboratory manual.
• Diagram: All the apparatus set-up in experiments should be drawn neatly and
precisely labelled.
• Results and data: Include the Datasheet Experiment with signature from
lab demonstrator or lecturer in this section. Report the measurements taken
during the experiment in a clear and organized way.
• Calculation: This section include the calculations from Datasheet
Experiment. Report all the calculations that you do and show the formulas
used to compute your results.
• Discussion:
i. Compare and comments the results obtained with the related
theory.
ii. If any result is not satisfactory, you should explain why and state
the correct/theoretical/expected results (if available).
iii. List any experimental factors that may have affected your results.
iv. If you think the experiment could be better using different
conditions or equipment, then state it here.
• Questions: Answer all the questions accurately.
• Conclusion: This section should be short, concise and straight to the point.
The conclusion discusses whether the results supported the hypothesis,
possible sources of error, and the lessons learned from the experiment.
• References: All background sources should be cited to the references using
correct format.
• Format, quality, Spelling, Punctuation, Grammar: The laboratory report is
typed and visually organised. The report contains one or fewer errors in
spelling, punctuation, and grammar
i) Journal/article:
Author (Year). Title of the article. Title of the Journal. Volume (Issue no.):
page.
Example:
Noor Rain, A., Khozirah, S., Mohd Ridzuan, M.A.R., Ong, B. K., Rohaya, C.,
Rosilawati, M., Hamdino, I., Badrul Amin and Zakiah, I. (2007). Antiplasmodial
Properties of Some Malaysian Medicinal Plants. Trop. Biomed. 24(1): 29-35.
ii) Book:
Author (Year). Title. (Edition). Placed published: Publisher.
Example:
th
Theusen, G. J. and Fabrycky, W. J. (1984). Engineering Economy. (6 Ed.).
Englewood Cliffs, N. J.: Prentice Hall.
4
EXPERIMENT 1
Objectives:
Introduction:
Heating by reflux is useful for dissolving a solid that only can be dissolved by prolonged
heating in a suitable solvent at boiling point. The loss of the solvent can be avoided by using
this method whereby as the solvent heated, the solvent vapor would be cooled at the surface
of the condenser and condensed back to its liquid form again.
Chemical(s):
2 g of crude/impure acetanilide
5
Apparatus:
An ice-bath
A bottle of distilled water
1 retort stand
1 50 ml or 100 ml round bottom flask
1 condenser
2 rubber hoses
1 adapter
1 heating mantle or suitable apparatus for heating the round bottom flask
1 filter paper
1 Buchner funnel
1 250 ml Buchner flask
1 vacuum pump
*Oven for drying (optional)
Procedure:
2. Clamp a clean 250 ml Buchner flask to a retort stand and put a Buchner funnel with a
filter paper to it. Wet the filter paper to ensure it lies flat to stop the crystals not to pass
through the edge and under the filter paper.
4. Pour solution containing the solid/crystals of acetanilide into the Buchner funnel. Apply
the vacuum. Stop the vacuum as soon as the liquid disappears.
5. Rinse the solid/crystals with cold solvent (i.e. water), then reapply the vacuum until the
solvent disappears.
6. Transfer the solid obtained into a suitable container and let it dry in an oven (optional).
Questions:
6
DATASHEET EXPERIMENT 1
PART A
Observation(s)
Others
7
PART B
Weight (g)
PART C
Weight(g)
Error(s)/Comment(s) Precaution
…………………………………………………
8
EXPERIMENT 2
Objective:
Introduction:
Simple distillation is the separation of a volatile liquid from a non-volatile substance. When
there is two or more mixture of volatile liquids with different boiling points needed to be
separate, distillation is termed as fractional distillation. For a liquid with a boiling point greater
than 250°C, vacuum distillation will be chosen instead to avoid decomposition of the liquid.
This is because the boiling point of a compound could be lowered when applied pressure is
reduced. Water condensers are used when the boiling point of the liquid is less than 100ºC.
Otherwise, an air condenser is to be used instead. The diagram of a simple distillation
apparatus is shown below.
Chemicals:
2 retort stands
1 50-100 ml round bottom flask
1 condenser
1 still head
1 thermometer
1 filter paper
2 rubber hoses
1 adapter
1 pocket thermometer
1 heating mantle
Procedure:
1. Fill the round bottom flask with 25 ml solution of 30% ethanol. Add a few boiling chips.
(Note: Never add boiling chips or a stir bar to a hot liquid. This can cause a seemingly
calm liquid to boil suddenly and violently.)
2. Set up the apparatus for a simple distillation as shown in the diagram. Put the
thermometer into the thermometer pocket.
3. When boiling, heat the liquid at constant rate, which is until the distillation rate is about 2-
3 drops per second.
4. Record a stable temperature as the boiling point of the liquid to be distilled. (Note: Do not
throw the boiling chips! Clean it and put it back into appropriate containers.)
5. Measure the ethanol collected after distillation and then, calculates the percentage yield
of recovery.
Questions:
10
DATASHEET EXPERIMENT 2
PART A: Record a stable temperature as the boiling point of the liquid to be distilled
Start:
End:
Volume (ml)
……………………………………………
11
EXPERIMENT 3
Objectives:
1. To learn the techniques of separating toluene from water (and other inorganic
compounds) by extraction
2. To learn the techniques of drying a dehydrated solution.
Introduction:
The partial removal of a molecular solute from one liquid (usually water) into another
immiscible liquid is call solvent extraction. The technique is use in organic chemistry. In the
laboratory, the two immiscible liquids are shaken thoroughly in a separating funnel fitted with
a good stopper. The tap is open at times during the shaking to release any pressure caused
by solvent vapor. A solvent such as ether is used because its boiling point is low and it can
be distilled from the extracted solution and recycled. In other hands volatile organic liquids
such as ether is dangerously flammable. Although water and ether is immiscible, water does
in fact, dissolve to some extent in ether. Due to this fact ether extracted is always dried
thoroughly with a suitable drying agent (such as anhydrous magnesium sulphate) before the
ether is distilled off. For a given volume of extracting solvent, it is more efficient to carry out
extraction by successive use of equal portions of the solvent rather than the use of the whole
volume in a single extraction.
Chemicals:
Toluene solution
Diethyl ether
Anhydrous magnesium sulphate
Apparatus:
1 separating funnel
1 retort stand
1 100 ml round bottom flask
1 condenser
1 still head
1 thermometer
1 filter paper
1 heating mantle
2 rubber hoses
1 adapter
1 pocket thermometer
12
Procedure:
2. Add 20 ml of diethyl ether and shake vigorously. While shaking, open the tap
occasionally to reduce the vapor pressure built up within, keep shaking until no more
pressure released from the solution (note: when there is no more hissing sound when
the tap is open). Leave to stand for 2 minutes or until the solution form two stable layers.
3. Open the tap, and then drain the diethyl ether layer containing toluene into a dry conical
flask. Use the remaining aqueous layer for a second extraction.
5. Dry the combined diethyl ether layers containing toluene with about half or one spatula of
anhydrous magnesium sulphate (or anhydrous calcium chloride) until a clear solution is
obtained (Not dissolve the compound). Filter out the drying agent.
(a) (b)
Figure 3: (a) Opening the tap to let out the gas and (b) separating the bottom layer
Questions:
1. When you are extracting an aqueous solution with an organic solvent, you are uncertain
of which layer in the separatory funnel is aqueous, how would you quickly sort out the
issue.
2. What is the purpose of using anhydrous magnesium sulphate in the experiment?
3. Draw the apparatus needed for extraction.
4. How do you estimate the anhydrous magnesium sulphate added is enough for the
solvent in the experiment?
13
DATASHEET EXPERIMENT 3
……………………………………….
14
EXPERIMENT 4
Objective:
To determine the melting points of various organic compounds and to use these to identify
unknowns
Introduction:
The melting point of a pure compound is an intensive property, like density and boiling point.
Intensive properties are independent of the amount of substance present. The melting point
of a compound is the temperature at which it changes from a solid to a liquid.
Experimentally, melting point is recorded as the range of temperatures in which the first
crystal starts to melt until the temperature at which the last crystal just disappears. The
determination of melting points can indicate the level of purity of a sample. An impure
compound melts over a wider range of temperatures, usually greater than 2 degrees. It also
helps to identify unknown samples, narrowing the number of possibilities, because a pure
solid melts reproducibly over a narrow range of temperatures. In this experiment, the identity
of an unknown organic compound will be determined by comparing its experimental melting
point to those of a variety of known compounds.
Chemicals:
Apparatus:
1 Mel-Temp apparatus
2 Capillary tubes
1 set of Mortar and pestle (optional)
1 Dropping tube
Procedure:
1. Obtain a capillary melting point tube (with one close end) and one known compound as
selected by your instructor. The known compound may need to be ground into a fine
powder with a mortar and pestle.
2. Place a small amount of the finely ground known compound in a weighing boat. Push the
open end of the capillary tube into the compound to load sample into tube. Load only 2-3
mm of sample into the tube. Larger samples will heat unevenly.
3. Hold the closed end of the capillary tube over a dropping tube; the dropping tube should
be held perpendicular to the table and on top of the table. Drop the capillary tube into the
dropping tube; the capillary tube will bounce on the table packing the powder into the
bottom. Remove the capillary tube from the dropping tube.
15
4. Place the capillary melting point tube in the Mel-Temp apparatus chamber, with the
opened end pointing outside the chamber.
6. Set the power level to obtain the desired heating rate. Start with a setting of 40, and
adjust if needed to control the rate of temperature increase. The sample should be
observed continuously, so that the melting point of the sample is not missed. Heat slowly
to acquire the most accurate results.
7. Record the melting range, which begins when the sample first starts to melt and ends
when the sample is completely melted. The known sample should melt within the range
of the its theoretical value respectively.
8. Turn off the Melt-Temp to allow it to cool to about 50°C before trying your unknown
sample.
9. Prepare a sample of your unknown (arranged by the instructor) in the same way that you
prepared the known sample and find its melting range.
10. Identify your unknown compound by comparing the experimental melting range of the
unknown compound to the melting points of the known compounds find out by your lab
mates.
Questions:
16
DATASHEET EXPERIMENT 4
…………………………………………
17
EXPERIMENT 5
REACTIONS OF HYDROCARBONS
Objective:
Introduction:
Alkanes are less reactive compared to alkenes and arenes. This is because carbon and
hydrogen atoms in alkanes have similar electronegativity values making the C-H bond not
polar. So, alkanes are not attacked by nucleophile but attacked by electrophile. Furthermore,
alkanes do not have unpaired / unshared electrons to be reactive towards acids or
electrophiles.
Alkenes on the other hand are more reactive than alkane due to the presence of π bond.
The π bond has high electron density and susceptible to react with electrophiles (electron
deficient species and low electron density).
Similarly to alkene, arenes have clouds of π electrons above and below its sigma bond
framework. Although benzene’s π electrons are in a stable aromatic system, they are
available to attack a strong electrophile to give a carbocation. We will study several reactions
of the hydrocarbons compound in this experiment.
Chemicals:
Hexane
Cyclohexene
Toluene
Br2 in CCl4
Acidified potassium permanganate solution (0.01M)
Apparatus:
6 test tubes
1 Bunsen burner
1 250 ml beaker
3 watch glasses
1 test tube holder
1 measuring cylinder
18
Procedures:
A. Combustion
(NOTE: Hexane, cyclohexene and toluene are flammable and immediately vaporize in air.
Close the chemical’s containers after you take it. Burn hexane, cyclohexene and toluene
simultaneously to observe the difference)
B. Saturation Test
1. Add 5 drops of Br2 in CCl4 to 2 ml of hexane in a test tube. Check the colour changes
(both for Br2 and hexane).
2. Repeat the test using cyclohexene and toluene.
C. Oxidation
(NOTE : make sure that the head of the test tube is at the safe direction where no one is
standing)
Questions:
1. Write the balance chemical equations for the combustion of hexane, cyclohexene and
toluene.
2. If benzene is mixed together with Br2 in CCl4, is there any reactions & color changes?
Explain your answer.
3. Write an equation for incomplete combustion of butane.
4. Give a suitable chemical test and its observation to differentiate butane and 1-butene.
19
DATASHEET EXPERIMENT 5
Reactions of Hydrocarbons
Test Observations
A. Combustion
B. Saturation test
C. Oxidation
………………………………………..
20
EXPERIMENT 6
Objective:
Introduction:
Reaction reactivity 3°>2°>1°>CH3> vinyl 3° < 2° < 1° < CH3 < vinyl
Effect of leaving group -I > -Br > -Cl>> -F -I > -Br > -Cl>> -F
Chemicals:
1-chlorobutane
1-bromobutane
2-bromobutane
tert-butyl chloride
acetone
18% Sodium iodide in acetone
1% ethanolic silver nitrate solution
ethanol
21
Apparatus:
Procedure:
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. Place 2-3 drops of each alkyl halide in individually labeled reaction tubes, add 0.5 mL of
an 18% solution of sodium iodide in acetone, mix the contents thoroughly and note the
time. Record the time of the first appearance of any precipitate.
3. If no reaction occurs within approximately 5 min, place the tube in a ~50°C water bath.
Watch for any reaction over the next 20 min. Record your observations. Rinse the
reactions tubes with ~0.25 mL of ethanol before proceeding to the next test.
1. Place 2-3 drops of 2-bromobutane in individually labeled reaction tubes and add:
a. 0.5 mL of 50:50 solution of acetone:18% sodium iodide in acetone at 50°C
b. 0.5 mL of 18% sodium iodide in acetone at 50°C (above in Part A(I))
2. Place 5-6 drops of 2-bromobutane in individually labeled reaction tubes and add:
a. 0.5 mL of 50:50 solution of acetone:18% sodium iodide in acetone at 50°C
b. 0.5 mL of 18% sodium iodide in acetone at 50°C
1. Place 2-3 drops of each alkyl halide in individually labeled reaction tubes as in part A of
this experiment, add 0.5 mL of a 1% ethanolic silver nitrate solution, mix the contents
well and note the time of addition and the time of the appearance of the first traces of
any precipitate.
2. Again, if no reaction occurs with approximately 10 min, place the tube in a ~50 °C water
bath and watch for any reaction over the next 10 min. Record your observations.
1. Place 2-3 drops of 2-bromobutane in individually labeled reaction tubes and add:
a. 0.5 mL of 50:50 solution of water:1% ethanolic silver nitrate solution
b. 0.5 mL of a 1% ethanolic silver nitrate solution at 50°C (above in Part B(I))
1. Arrange the following in order of increasing rate of substitution by the SN2 mechanism:
1-bromobutane, 2-bromobutane, 2-bromo-2-methylpropane
2. Arrange the compounds in question (i) in order of increasing rate of substitution by
the SN1 mechanism.
3. What would be the effect of carrying out the sodium iodide in acetone reaction with
the alkyl halides using an iodide solution half as concentrated?
4. Provide an equation, clearly showing the stereochemistry of the starting material and
the product, for the reaction of 2-bromobutane with sodium iodide in acetone.
23
DATASHEET EXPERIMENT 6
Test Observations and time taken of the first appearance of any precipitate or after
warm at 50 °C
A(I).
0.5 mL of 18%
sodium iodide
in acetone
B(I).
0.5 mL of a
1% ethanolic
silver nitrate
solution
Effect of Concentration
Test Observations and time taken of the first appearance of any precipitate or
after warm at 50 °C
A(II).
2-3 drops
2-bromobutane
5-6 drops
2-bromobutane
24
Effect of Solvent
Test Observations and time taken of the first appearance of any precipitate.
B(II).
2-3 drops
2-bromobutane
....................................................
25