Experiment on Solubility of Organic Compounds

Aggabao, Zeena T.
Balleras, Ezracel Vonn Mildred M.
Bolok, Precious Michaela A.
Cabreros, Danielle C.
Chuidian, Naomi P.
Correos, Jenus Q.
Galang, Ashley Lawrence S.

MEB12
De La Salle University - Dasmarinas
Dasmarinas, Cavite Philippines

ABSTRACT

The experiment aimed to classify unknown organic compounds by evaluating their

solubility in various solvents and assigning each to a specific group based on
functional group characteristics. Tests involved adding each compound to water,
sodium hydroxide (NaOH), sodium bicarbonate (NaHCO₃), and hydrochloric acid
(HCl) to assess solubility behavior and determine the functional groups present.
Compounds were classified into groups based on solubility patterns: Group A
included small alcohols and ketones; Group B1, carboxylic acids; Group B2, phenols;
Group C, amines; and Group D, hydrocarbons. Experimental results were compared
with expected solubility classifications, revealing some inconsistencies. For instance,
only Compound 3 matched its predicted group, while others diverged, possibly due to
small sample sizes, contamination, or human error in measurement and observation.
These factors likely contributed to inaccurate classifications.

INTRODUCTION

Solubility is considered one of the basic properties of a compound. It is of prime importance for
the explanation of its chemical character, for the evaluation of its polarity, and for its characterization as
distinct from other compounds. It further forms a useful means for the study of the application potential of
a substance. In organic chemistry, solubility often reflects the interaction between molecules, and thus
can be in a position to know whether certain functional groups are present within the compound. Tests of
solubility are the most important to identify and characterize compounds. This experiment attempts to find
the solubility of five organic compounds in different solvents, namely water (H₂O), sodium hydroxide
(NaOH), sodium bicarbonate (NaHCO₃), and hydrochloric acid (HCl). The study about the solubility of
compounds in different solvents makes one understand that some functional groups are there and offers
a good idea of their chemical properties. The solubility patterns observed for each of the compounds in
these solvents can be used to deduce information regarding their molecular structure and polarity. Thus,
these results from the solubility tests are of paramount importance to identify and characterize
compounds under study.
MATERIALS & METHODS

Organic compounds are classified into different families and classes based on their functional
groups. Every functional group in organic compounds has unique chemical characteristics that emphasize
its distinction from each other. These properties can be observed through solubility behavior, by
undergoing a test of a compound’s solubility through different solvents to gain an understanding of its
nature. Ultimately, these classifications undermine the chemical behavior which aids in predicting and
gaining insights into its interactions in various chemical contexts. The primary goal of this experiment is to
determine the solubility behavior of unknown compounds through solubility tests and categorize them
according to their respective classifications. Table 1 was used to determine the group of each compound.
To begin, obtain approximately 3 drops (or 3 mg) of compound 1 and add 3 mL of distilled water. Shake
the mixture and observe whether the compound dissolves. If compound 1 completely dissolves in water, it
is classified as Group A. If compound 1 does not dissolve in water, obtain a new sample of compound 1
and add 3 mL of 5% NaOH. Shake and observe its solubility. If the compound dissolves in NaOH, test its
solubility further by adding 3 mL of 5% NaHCO₃. If the compound dissolves in both NaOH and NaHCO₃, it
is classified as Group B1, whereas if it dissolves in NaOH but remains insoluble in NaHCO₃, it belongs to
Group B2. If compound 1 is insoluble in NaOH, obtain a new sample and add 3 mL of 5% HCl. Shake and
observe. If the compound dissolves in HCl, it is classified as Group C; if it does not dissolve, it belongs to
Group D. Repeat these steps for compounds 2, 3, 4, and 5, classifying each based on the solubility
behavior observed in water, NaOH, NaHCO₃, and HCl.

Table 1. Solubility Classification of Organic Compounds

Classification General Characteristics

A ● May be alcohols, ketones, amines, carboxylic acids with < 5 carbon atom

B1 ● May be carboxylic acids with more > 5 carbon atoms

● Phenols with electron withdrawing groups

B2 ● Phenols

C ● Amines

D ● Hydrocarbons, alkyl halides, alcohols, aldehydes, ketones with > 5 carbon

atoms

RESULTS & DISCUSSION

Table 2. Experimental Results of Solubility Classification of Organic Compounds

Compound Observation Experimental
Results

H20 5% NaOH 5% HCl

NaHCO3

1 soluble A
 2 soluble A

3 soluble A

4 insoluble soluble insoluble B2

5 insoluble insoluble insoluble insoluble D

Table 3. Expected Solubility Classification of Organic Compounds

Compound Observation Correct
Classification

H20 5% NaOH 5% HCl

NaHCO3

1 immiscible immiscible immiscible D

2 immiscible miscible immiscible B2

3 miscible A

4 insoluble soluble soluble B1

5 insoluble insoluble soluble C

The experimental results seen in Table 2 revealed that the classification of organic compounds
1-5 did not entirely align with the expected classifications in Table 3. Compound 3 was the only compound
classified correctly, categorized under Group A. Several factors may have contributed to the incorrect
solubility classification of the other compounds. Firstly, the small quantities of chemicals used in the
experiment limited the observable changes in solubility tests. This made it difficult to accurately
distinguish between closely related functional groups. Secondly, potential contaminants present in the
chemicals could have interfered with the expected reactions which lead to inconclusive results.
Additionally, human error in conducting the experiments, such as imprecise measurements or incorrect
observations, might have influenced the classification outcomes.

The structure of each compound is illustrated in Figure 1.

Figure 1. Structure of Organic Compounds

Compound 1, Hexane, is a nonpolar hydrocarbon with a linear structure and no polar functional
groups. Its nonpolar nature renders it insoluble in polar solvents like water, NaOH, NaHCO3, and HCl, as
it cannot form hydrogen bonds or ion-dipole interactions with these solvents(1). Compound 2, Phenol,
contains a benzene ring with a hydroxyl group which is a polar component. This allows for slight water
solubility through hydrogen bonding, but the nonpolar benzene ring limits overall solubility. Phenol reacts
with NaOH to form a water-soluble phenoxide ion, explaining its solubility in this base(2). It is insoluble in
NaHCO3 and HCl due to a lack of reactivity with these reagents. Compound 3, categorized as Ketones,
possesses a carbonyl group (C=O). Smaller carbonyl compounds with fewer carbon atoms exhibit higher
water solubility due to hydrogen bonding, while larger compounds with longer nonpolar chains become
less soluble(4). These compounds generally do not react with NaOH, NaHCO3, or HCl, resulting in
insolubility in these solutions. Compound 4, Benzoic acid, contains a benzene ring with a carboxylic acid
group (-COOH), making it acidic. This allows it to react with both NaOH and NaHCO3 to form
water-soluble carboxylate salts(5). Benzoic acid is slightly soluble in water due to limited hydrogen
bonding and is insoluble in HCl as it does not react with this acid. Compound 5, Diphenylamine, consists
of two phenyl groups connected by an amine group (-NH-), imparting basic properties. It reacts with HCl
to form a water-soluble ammonium salt, but its large nonpolar phenyl groups limit overall solubility.
Diphenylamine is insoluble in water, NaOH, and NaHCO3 due to limited polarity and inability to form
significant intermolecular interactions with these solvents(5).

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