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ORGANIC CHEMISTRY 1
LABORATORY (Instruction sheets)
Contact hours: 3 hours/week
Laboratory textbook: Pavia, Lampman, Kriz and Engel, Introduction to Organic
Laboratoy Techniques 3rd Edition (2011)
** Students MUST obtain a copy of the textbook
Synopsis
This is an organic chemistry practical course which reinforce the theory and concepts studied
in Organic Chemistry 1 (CHM456). It covers the learning of simple laboratory techniques
such as reflux, distillation, extraction, crystallization and melting point determination,
preparations of organic compound and separation of mixtures.
The Techniques
Students are REQUIRED to read and understand the various techniques that will be covered
in the laboratory sessions from the textbook.
Techniques Page
1 Laboratory Safety 6
2 Laboratory Glassware 31
3 Measurement of Volume and Weight 39
4 Heating and Cooling Methods 58
5 Reaction methods (eg: distillation, reflux) 68
6 Filtration 90
7 Physical Constants of Solids: The Melting Point 103
8 Crystallization: Purification of Solids 122
9 Extractions, Separations and Drying Agents 141
10 Simple Distillation 179
11 Thin Layer Chromatography 261
Laboratory Report
A well written report is vital to achieving a good grade. Besides conducting the experiments
carefully, the students are expected to write a good report which will reflect a good
understanding of chemistry behind the experiments.
1. All laboratory report MUST BE submitted one week after the experiments.
2. The cover page should contain the following information:
Course Name
Course Code
Number and Title of Experiment
Name of Student
Name of Partners (for group work)
Name of Lecturer
Date of Experiment
Date of Submission of report
3. The following marking scheme table must be included with the laboratoy report (at
cover page as well)
4. Should the student fail to submit the weeks report, the mark will only given based on
the rubrics mark for the experiment. Marks will also be deducted for late
submission of report.
5. No report will be accepted (no marks given) from students who did not perform the
weeks experiment.
6. Students who missed any lab session (with medical certificate) will be graded based
on the remaining number of experiments.
7. No copying is allowed. If two students have similar reports, their marks will be
divided by two.
Title of Experiments
WEEK CONTENTS
3 Acid-Base Extraction
4 Preparation of 4-methylcyclohexene from dehydration of 4-methylcyclohexanol
5 Preparation of 1-bromobutane from 1-butanol
6 Preparation of acetylsalicylic acid
7 Nitration of methyl benzoate
8 Thin Layer Chromatography (TLC): TLC analysis of analgesic drugs
9 Friedel-Crafts acylation
Experiment 1
In this experiment you will separate a mixture of an acid (benzoic acid) and a neutral
compound (triphenylmethanol OR 1,2,4,5-tetrachlorobenzene) into its components by
extraction. The mixture is dissolved in diethyl ether. Both components are soluble in this
solvent. Then a 1 M NaOH solution is used to extract the benzoic acid in the form of its
water-soluble salt, sodium benzoate (three extractions to ensure complete removal), leaving
the neutral compound in the ether layer. The three aqueous extracts are combined, and the two
components are recovered as follows:
1. The neutral compound by washing, drying and evaporating the ether layer
2. Benzoic acid by acidifying the aqueous layer to form benzoic acid, which precipitates.
The benzoic acid is then recovered by filtration, washed and dried.
In the text book, you are required to add 0.36 g of an unknown mixture to a screw-cap
centrifuge tube [0.36g are consist of mixtures of 0.24g unknown and 0.12g benzoic acid]
Referring to paragraph 3 in the text book, after adding 6M HCl to each of the two flask until
the mixtures are acidic, cool both the flask in an ice bath for about 15 minutes or until
thoroughly chilled. Collect the solid benzoic acid using Buchner funnel and filter flask. Wash
with 2-3ml of your chilled water, and allow the suction to continue for 5 minutes to get the
solid as dry as possible. Gently scrape it into a watch glass and complete the dryinhg process
in the oven. Weigh the solid and obtain a melting point. Assuming that exactly half the
original mixture was benzoic acid, calculate the percent recovery.
As for the rest of the procedure, follow the instructions in the text book till the end.
Report
1. List four water-immiscible liquids other than ether that could be used to extract
organic compounds from aqueous solution.
3. Draw the structure of the product when benzoic acid reacts with sodium hydroxide.
Why is the product of this reaction easily extracted into H2O, while the original
benzoic acid is not so easily extracted into H2O?
4. Why does benzoic acid precipitate out when the aqueous layer is acidified with HCl?
Apparatus assembly
o Weight an empty and clean 50ml round-bottom flask (RBF) before you place
7.5ml of 4-methylcyclohexanol in it
o Using graduated pipette, place 7.5 ml of 4-methylcyclohexanol in the RBF
Dehydration
o Maintain the distillation temperature below 100C. Continue until only 0.5-0.6
ml of residue remains in the distillation flask or the mixture begins to smoke or
bump
Distillation
o Make sure you get rid of the drying agent before starting with distillation
process
o The 25ml RBF use as a receiver must be pre-weigh.
o The boiling point of your 4-methylcyclohexene is the temperature range over
which most of the product distills.
Spectroscopy
o No need to do this part
Unsaturation test
o This test must be done and record your result and explain them.
Question:
Additional question:
This experiment introduces nucleophilic substitution reaction, specifically the second order
nucleophilic substitution, or SN2. In this experiment, sodium bromide and 1-butanol are
dissolved in water. Sulfuric acid is added cautiously which generates hydrobromic acid,
which in turn reacts with the alcohol upon heating to make 1-bromobutane.
Procedure:
Question:
In this experiment, the hydroxyl group (-OH) on the benzene ring in salicylic acid reacts with
acetic anhydride to form an ester functional group. Thus, the formation of acetylsalicylic acid
is referred to as an esterification reaction. The reaction requires the present of an acid catalyst
(we will use concentrated sulphuric acid), indicated by the H+ above the equilibrium arrows.
The product is filtered, washed, test for purity using Ferric Chloride and recrystallized from
ethyl acetate.
Procedure:
4. Observed melting point of acetylsalicylic acid and compare it with the literature value
Question:
In this experiment, you will put a nitro (-NO2) group on a benzene ring which already has an
ester group attached to it (methyl benzoate). The nitration of methyl benzoate to prepare
methyl m-nitrobenzoate is an example of an electrophilic aromatic substitution reaction, in
which a proton of the aromatic ring is replaced by a nitro group.
Question:
Additional question:
Title: Thin Layer Chromatography (TLC): The analysis of analgesic drugs [PAGE 488]
In this experiment, TLC will be used to examine the composition of a known analgesic (pain
relieving) drug such as panadol. Several common analgesic are aspirin and acetaminophen.
Caffeine is sometimes added to these formulations to overcome drowsiness. In addition to the
active ingredients, the tablets of these drugs contain starch, lactose, and other substances that
act as binders and permit rapid solution, and sometimes also inorganic bases. The objective if
this experiment is to identify the components of this analgesic tablet by TLC comparison with
standard compounds.
Procedure:
1. Calculation of the Rf values of the reference compounds and the components of the
analgesic drug
2. Draw the chromatogam to scale in your lab book; identify and label the spots in the
chromatogram, including as many of the spots on the plates as possible
3. From the number, position and appearance of the spots on the plate, identify the
components in your analgesic drug
Question: