CHM457

FUNDAMENTAL ORGANIC CHEMISTRY

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 Fundamental Organic Chemistry (CHM457). 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 Note Book/Jotter

Do not come into a laboratory unprepared. Read and understand the experiments ahead of
time; no more reading should be done during lab session. If you do not do this, you will be
unable to plan and use your time efficiently. There are several lab techniques that you need to
read on your own for each lab session for example distillation, extraction, crystallization etc.
They are self-explanatory and if you are unclear about something always consult the lecturer.
Students must write/draw a brief outline/flowchart of the procedure of the experiment before
coming to the lab. Your note book will be checked by your lecturer for assessment.
Please read Technique 2 on PAGE 23 on the Laboratory Notebook, Calculations and
Laboratory Records carefully. The laboratory note book is mandatory and a student will not
be allowed to conduct the experiment without a laboratory note book. Only hard bound
notebook is acceptable. This note book is required for the pre-laboratory preparations as well
as recording results, data and observation of each experiments. The pre-laboratory
preparations must include not only procedural notes but also reactions and calculations.
Assessment and Grading
The laboratory sessions contribute 20% (15% laboratory report, 5% rubrics for laboratory
skills) of the course grade. The success of your experiments will depend on how well you
conduct the expeiments to achieve the objectives. This is reflected in the marks obtained. The
marks for each experiments will come from the following:

A. Laboratory Reports 30 marks

(all reports are individual work)
B. Rubric for Laboratory Skills 20 marks
• Pre-laboratory preparations
• Handling chemicals and apparatus
• Organization of work
• Time management
• Observation of products

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)

Allocated mark Mark

Aims/Objectives of the experiment 2
Introduction 3
Experimental procedure 3
Results and Observations 4
Calculations 4
Discussions 6
Conclusions 2
Questions 5
References 1
TOTAL 30
 4. Should the student fail to submit the week’s report, the mark will only given based on
the rubric’s 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
week’s 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
Experiment 1

Title: Acid-Base Extraction (PAGE 458)

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.

Melting points and yield are determined for BOTH products.

Procedure (add on):

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

The report that you submit must include:

Actual weight of benzoic acid

Weight of benzoic acid recovered

Observed melting point of benzoic acid

Percent recovery of benzoic acid

Actual weight of unknown sample

Weight of unknown sample recovered

Observed melting point of unknown sample

Percent recovery of unknown sample

Answer the questions below:

1. List four water-immiscible liquids other than ether that could be used to extract
organic compounds from aqueous solution.

2. Why is it wrong to leave a bottle of anhydrous sodium sulphate or calcium chloride

open?

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?

5. Develop a procedure for isolating a neutral compound from a mixture containing a

basic impurity by drawing a flow chart.
Experiment 2

Title: Preparation of 4-methylcyclohexene from dehydration of 4-methylcyclohexanol

(PAGE 561)

In this experiment, 4-methylcyclohexanol undergoes acid-catalyzed dehydration to give 4-

methylcyclohexene. The product is distilled from the reaction flask along with the water
generated. The distillate is washed with salt solution, dried and distilled.

Required reading: Technique 5 and 6

Technique 12- Extractions, separations and drying agents, Section 12.7,

12.8 and 12.9

Technique 14- Simple distillation

Procedure (add-on reminders):

• 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 100°C. Continue until only 0.5-0.6
ml of residue remains in the distillation flask or the mixture begins to smoke or
bump

• Isolation and drying of the product

o Transfer the distillate to a separatory funnel with the aid of 3ml saturated
sodium chloride solution (you don’t have to use centrifuge tube and Pasteur
pipette)

• 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.
The report that you submit must include:

1. Theoretical yield calculation (SHOW WORK)

2. Percentage yield calculation of 4-methylcyclohexene (SHOW WORK)

3. Observed boiling point and literature boiling point of the product.

Question:

Only answer question 1,2 and 5 from the text book.

Additional question:

Show the complete acid-catalyzed mechanism for the dehydration of 2-methylcyclohexanol.

Experiment 3

Title: Preparation of 1-bromobutane from 1-butanol (PAGE 557)

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.

Required reading: Techniques 5,6,7,12 and 14

Procedure:

• Follow all the procedures from the text book

• Before starting the distillation process, don’t forget to pre-weigh the RBF use as
receiver
• You don’t have to do the determination of IR spectrum of the product

The report that you submit must include:

1. Theoretical yield calculation of 1-bromobutane (SHOW WORK)

2. Actual yield 1-bromobutane (mass and volume)

3. Percentage yield calculation of 1-bromobutane (SHOW WORK)

4. Observed boiling point and literature boiling point of 1-bromobutane.

Question:

Answer all questions on page 560-561 (n-butyl bromide only)

Experiment 4

Title: Preparation of Acetylsalicylic Acid (Aspirin) [PAGE 481]

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.

Required reading: Techniques 5 (Measurement of volume and height), 6 (Heating and

cooling methods), 7 (Reaction methods, Sections 7.1, 7.4-7.6), 8 (Filtration, Section 8.1-8.6),
9 (Physical constants of solid: The melting point), 11 (Crystallization: Purification of solids)

Procedure:

• Follow all the procedures from the text book

The report that you submit must include:

1. Theoretical yield calculation of acetylsalicylic acid (SHOW WORK)

2. Actual yield acetylsalicylic acid

3. Percentage yield calculation of acetylsalicylic acid (SHOW WORK)

4. Observed melting point of acetylsalicylic acid and compare it with the literature value

Question:

Answer all questions on page 484 except question 4.

Experiment 5

Title: Nitration of Methyl Benzoate [PAGE 698]

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.

Required reading: Technique 11 (Crystallization: Purification of solids)

Procedure (add-on reminder):

• Follow all the procedures from the text book

• Reminder: To prepare your H2SO4/HNO3 mixture, add 2 ml of concentrated sulphuric
acid to 2 ml of concentrated nitic acid in a small test tube. Cool this acid mixture in an
ice bath prior to using.
• Reminder: Recrystallize your crude product using an equal weight of methanol as your
recrystallization solvent (for example, if your product is 3 g then use 3 ml of methanol.
Use a minimal amount of solvent (< 5ml will be enough) for this
recrystallization.Collect the purified product by vacuum filtration and wash with a
little cold methanol. Dry, weigh and determine the melting point. Use the melting
point to identify the isomer you have produced (ortho/meta/para)
• No need to do the IR spectrum

The report that you submit must include:

1. Theoretical yield calculation of methyl m-nitrobenzoate (SHOW WORK)

2. Actual yield of methyl m-nitrobenzoate

3. Percentage yield calculation of methyl m-nitrobenzoate (SHOW WORK)

4. Observed melting point of methyl m-nitrobenzoate

Question:

Answer all questions on page 702 except question 4.

Additional question:

Write the full mechanism for the nitration of methyl benzoate.

Experiment 6

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.

Required reading: Essay 2 (Analgesics), Essay 3 (Identification of drugs), Technique 20

(Thin-layer Chromatography)

Procedure:

• Follow all the procedures from the text book

The report that you submit must include:

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:

Answer all questions on page 492