DE LA SALLE UNIVERSITY -DASMARIAS

College of Science and Computer Studies

PHYSICAL SCIENCES DEPARTMENT
City of Dasmarias, Cavite

GUIDELINES FOR PRE-LABORATORY AND POST-LABORATORY REQUIREMENTS

FOR ORGANIC CHEMISTRY

A. Introduction
Scientific writing is part of the job description of a researcher in the fields of Science, Medicine, and
Engineering. A scientific paper is a technical paper that communicates the results of significant studies,
discoveries, or inventions in these fields. It disseminates pertinent information so others in the same or related
fields can benefit from them. This document is open for validation in terms of accuracy, reliability, and
repeatability of results. Thus, a scientific paper becomes a part of creating and validating new knowledge,
techniques, discoveries, and inventions.
As a student in Chemistry laboratory, you will be required to write scientific paper based on the results of
your class experiments. This will serve as an important training ground for you as research-proficient scientists,
medical & allied health science practitioners, engineers, and educators in the future.
The training will include preparation of schematic diagram of experimental procedures as a pre-laboratory
requirement; and completion of experimental worksheets and writing of scientific paper as post-laboratory
requirements.
B. Schematic Diagram of Experimental Procedures
The writing of schematic diagram will train you in summarizing and understanding technical procedures in
conducting scientific experiments. A schematic diagram is a stepwise flow chart of the experimental procedures
that can be easily understood and interpreted. The process of making this flow chart will require an active reading
and understanding of the described procedures. This will enhance your skills in interpreting technical procedures
and will train you in critiquing existing protocols so as to improve them or even design your own experiment.
Clarity and brevity is a must in this process. These characteristics are illustrated in the sample schematic
diagram in Figure 1. It is required of every student in all Chemistry laboratory classes as a pre-laboratory output.
It is an absolute requirement before you may conduct an experiment: NO PRE-LAB MEANS NO EXPERIMENT!
This schematic diagram is previously written on the required laboratory notebook. However, in view of minimizing
waste of resources, it can be hand-written or computerized in a single bond paper (81/2 x 11) or on the provided
schematic diagram sheet in the existing edition of your laboratory manual. The schematic diagram will also serve
as the basis of pre-laboratory discussion. This should also be consulted throughout the experimentation period for
a more efficient performance of the experiment.
C. Experimental Worksheet
The worksheet is where you write-down your pertinent observations, data, analysis and calculations
during and after experimentation. Accuracy, intellectual honesty, and neatness should be observed in completing
your worksheet. You should also research for the answers on the follow-up questions in each experiment. Each
portion will have corresponding points for grading. Initial entry of data may be done in pencil but the final output
should always be written in black or blue pen. Raw data and calculations should always be shown to your
laboratory instructor before the end of your laboratory period for inspection and countersigning. Some parts of

post-experimental analysis may be required for accomplishment during the laboratory period as stipulated by your
instructor. However, the bulk of the analysis will serve as assignment that is due a week after finishing the
experiment. The worksheet is detached from the manual upon submission, but you may photocopy it prior to
submission for personal reference.

Figure 1: Sample Schematic Diagram of Experimental Procedures

D. Scientific Paper
The scientific paper is a technical paper that discusses the experimental results and their interpretations,
implications, and applications. The format that you will follow is the standard used in many international scientific
journals. The paper is accomplished individually and is due one week after finishing the experiment. It should
be computerized and printed on 8 x 11 bond paper, single-spaced, and in Arial 10 font. Below is the
breakdown of the parts of a scientific paper and their description. A sample scientific paper is also given as
reference.
1. Heading the title of the experiment in bold letters (Arial 12) with the name of the author(s) in bold
letters and their affiliation(s) below.

2. Abstract this is the study itself in a nutshell. The topic, over-all procedures, results, and
interpretations are summarized in a concise highlighted paragraph. Bulk of the abstract should give
focus on the results and their significance.
3. Introduction this gives a brief scientific background of the study and the hypothesis/assumptions of
the experiment. References are cited as numbers in parenthesis within the text and are listed in the
order that they are cited.
4. Materials and Methods this summarizes the materials used and the experimental procedures
conducted. The concentration and amount of each reagent and the brand & model of the analytical
instruments used (if any) should also be explicitly stated. The stepwise procedure should be
mentioned in past tense. References are cited as numbers in parenthesis within the text and listed in
the order that they are cited.
5. Results and Discussions this section shows the experimental results and their interpretations,
implications, and applications. Pertinent data should be summarized through necessary tables and
graphs. Important reactions, equations, and mechanisms should likewise be shown. Strictly use
Chem Sketch program for illustrating chemical structures and reactions . Possible sources of
errors should be analyzed and the possible remediation should be suggested. References are cited
as numbers in parenthesis within the text and listed in the order that they are cited.
6. References they should be cited according to the order of mentioning in the paper. Always cite the
laboratory manual that you are using as one of your references. Reputable references include books,
laboratory manuals, thesis, scientific journals (printed and on-line), and websites of reputable private
scientific agencies & organizations, government scientific agencies, and Science departments of
various universities and colleges. Wikipedia, although a very useful on-line references, is not
accepted as reliable one because of lack of strict peer-review system. Check-out the library for
available reference materials. Do not copy any work word-for-word but paraphrase them in your own
words then properly cite the source as stipulated. Failure to do so might be tantamount to plagiarism
which is a criminal act as per Intellectual Properties Rights (IPR) Law. Examples of proper citation
are given below:
a. Textbook or Laboratory Manual
1. Clark, J.M. Experimental Biochemistry. 3rd Ed. 1994. W.H. Freeman and Company. USA
b. Scientific Journal
2. Haliwell, B.; Gutterridge, J. M.C. Oxygen toxicity, oxygen radicals, transition metals and
disease. Biochem. J. 1984, 219;1-4.
c. Website with author under an organization
3. Dollard, K. DNA Isolation from Onion. Access Excellence at National Health Museum.
2008. Retrieved 15 October 2008 from http://accessexcellnece.org/AE/AEC/AEF
1994/dollard_onionDNA.php
d. Website of an organization, no specific author
4. Genetics Science Learning Center. Stem Cells". Learn Genetics. 2008. Retrieved 15
October 2008 from http://learn.genetics.utah.edu/content/tech/stemcells.
e. Thesis
5. De La Cruz, J. The Antioxidant Properties of Philippine Vegetables. Unpublished
Undergraduate Thesis. 2005. De La Salle University-Dasmarias, Dasmarias City,
Cavite, Philippines.

Solubility of Organic Compounds

Gideon A. Legaspi
De La Salle University-Dasmarias
Dasmarias City, Cavite, Philippines

ABSTRACT
The solubility characteristics of various organic compounds were used in classification and
identification of possible functional groups that they possess. Small amounts of five unknown
samples were tested for their solubility in water, NaOH, NaHCO 3, and HCl. Sample 1 is
insoluble in all the solvents, hence was classified in Group D which includes hydrocarbons and
high molecular weight organic compounds. Sample 2 was categorized in Group B2 as it is
soluble only in NaOH, indicating that it is phenolic compound. Meanwhile, sample 3 was
lumped in Group A as it is neutral and water-soluble; thereby indicating that it might be a low
molecular weight alcohol, aldehyde, or ketone. Sample 4 was classified in Group B1 as it is
soluble both in NaOH and NaHCO3, implying that it is a carboxylic acid. Lastly, sample 5 was
categorized in Group C as it is soluble in HCl, which indicates that it is an amine. The true
identity of the samples was later revealed as hexane, phenol, acetone, benzoic acid, and
diphenylamine respectively. The results of the experiment are therefore accurate and have
been useful in classifying and determining their probable functional group.

INTRODUCTION
The solubility of organic compounds is determined by number of carbon chain and functional group that
they possess. Normally, organic compounds would be water insoluble due to the nonpolar bond formed by
carbon and hydrogen atoms. However, the presence of polar moieties such as hydroxyl (-OH), carbonyl (C=O),
carboxyl (-COOH), and amino (-NH 2) functionalities would make them appreciably soluble in water. In addition,
some of these moieties would give an acidic or basic characteristic to the compound such as carboxyl and amino
group in respectively (1). Such solubility behavior may therefore be used in identifying the possible functionalities
that is present in an organic sample which was done in this experiment.

MATERIALS AND METHODS

Five unknown organic compounds were tested for their solubility in water, 5% NaOH, 5% NaHCO 3, and
5% HCl. In general, 5-10 drops of each liquid sample and 5-10 mg of each solid sample were used for solubility
testing in about 1.00-2.00 ml of the given solvents. Furthermore, litmus paper test was used to determine whether
the compound is acidic, basic, or neutral in nature. Base on the solubility profile of each sample, they were
classified as to Group A, B1, B2, C, or D as summarized in the given schematic diagram in Figure 1.

Figure 1. Classification Scheme of Organic Samples Based on Solubility Behavior

RESULTS AND DISCUSSION

The solubility profile of organic compounds is useful in classifying and identifying the functional moieties
that they possess. Such profile where determine for five samples and the experimental results are summarized in
Table 1.
Table 1. Solubility Profile of Organic Samples and Their Classification
Compound
H2O
1
2
3
4
5

++
-

Observation
5%
5%
NaOH
NaHCO3
++
NT
NT
++
+
-

Classification
HCl
NT
NT
NT
+

Group D
Group B2
Group A
Group B1
Group C

Legend: ++ completely soluble; + slightly soluble; - insoluble; NT not tested

Sample 1 is insoluble in all the solvents used, hence was classified in Group D which includes
hydrocarbons and high molecular weight organic compounds. Sample 2 was categorized in Group B2 as it is
soluble only in NaOH, indicating that it is phenolic compound. Meanwhile, sample 3 was lumped in Group A as it
is neutral and water-soluble, thereby indicating that it might be a low molecular weight alcohol, aldehyde, or
ketone. Sample 4 was classified in Group B1 as it is soluble both in NaOH and NaHCO 3, implying that it is a
carboxylic acid. Lastly, sample 5 was categorized in Group C as it is soluble in HCl, which indicates that it is an
amine. The true identity of the samples was later revealed as hexane, phenol, acetone, benzoic acid, and
diphenylamine respectively thereby confirming the accuracy of the obtained results.

H3C

H3C
CH3

CH3
phenol

hexane

acetone

OH
NH

diphenylamine

benzoic acid

Figure 2. Structures of Organic Samples Used

Hexane is expected to be insoluble in all the solvents since it is nonpolar and neutral in nature. The C-C
and C-H bonds have no significant difference in electronegativity resulting to a negligible net dipole moment,
hence, the nonpolar nature (2). Phenol is also significantly soluble in water due to the nonpolarity of the benzene
ring. Phenol is however quite acidic in nature, hence it dissolves in NaOH due to acid-base reaction where the
OH group is deprotonated to form a phenoxide anion which then attracts Na + to form sodium phenoxide salt as
illustrated in Figure 3.
-

OH

O Na

NaOH

Phenol

H2O

Sodium phenoxide

Figure 3. Reaction of Phenol with Sodium Hydroxide

Acetone is a low molecular weight ketone which is completely soluble in water due to the polar nature of
the carbonyl (C=O) moiety. Benzoic acid, on the other hand, is an aromatic carboxylic acid which like phenol is
insignificantly soluble in water due to the nonpolar benzene ring. However, it is a much stronger acid than phenol;
hence it dissolves both in NaOH and NaHCO 3. The reaction involves the formation of the sodium carboxylate salt
as illustrated in Figure 4.
O

OH

NaOH

Benzoic acid

Benzoic acid

H2O

Sodium benzoate

OH

O Na

O Na

NaHCO3
Sodium benzoate

H2CO3
Carbonic acid

Figure 4. Reaction of Benzoic acid with Sodium Hydroxide and Sodium Bicarbonate

Lastly, diphenylamine is quite basic in nature because the amino group is capable of accepting proton. It
would therefore react significantly with HCl to form an ammonium chloride salt as illustrated in Figure 4. The
reaction is however limited due to the presence of two benzene rings which limits the solubility of the compound
even in HCl. Over all, the results of the experiment are accurate and have been useful in classifying and
determining the probable identity of organic compounds by correlating their solubility profile with their functional
group. However, solubility testing is quite basic and limited. More specific chemical tests may be used in order to
determine the functional group in a sample. For example, phenol is detected through ferric chloride test where
phenol can form a violet or greenish complex with the reagent. Other tests for each functional group exist but
they will require specific reagents and reaction conditions (3,4).
Cl+

NH2

NH

+
Diphenylamine

HCl

Diphenylammonium chloride

Figure 4. Reaction of Diphenylamine with Hydrochloric acid

REFERENCES
(1) Schmid, G. H. 1996. Organic Chemistry. Organic Chemistry. USA: Mosby Year Book.Inc.
(2) Morrison, R. T. and Boyd, R. N. 1998. Organic Chemistry. 6th edition. USA: Prentice Hall International, Inc.
(3) McMurry, J. 2008. Fundamentals of Organic Chemistry. 7th edition. USA: Prentice Hall International, Inc.
(4) Legaspi, G. A. and Sta. Ana, S.T. Essentials of Organic Chemistry Laboratory. 2010. Philippines. (Evaluation
Copy)

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of

Sample

Scientific

Prepared by:

Gideon A. Legaspi, MS
Laboratory Supervisor
Assistant Professor V
Physical Sciences Department
College of Science and Computer Studies
De La Salle University-Dasmarias

11/4/13