Solubility of Organic Compounds

Yvonne Maranan
Allysha Milanes
Kimberly Anne Moscosa

De La Salle University-Dasmarias
Dasmarias, Cavite, Philippines

ABSTRACT

The main concept of the experiment was to investigate the solubility of organic
compounds in a given solvent. We also aim to identify an organic compound through
qualitative analysis, which includes solubility characteristics and functional group tests.
H2O ,
We were able to test five organic compounds against solvents such as
NaOH , NaHCO and HCl. 3 mg of every compound was obtained and 3
ml of water was added in five of the samples to test solubility. It was found that a
compound with homogenous mixture is said to be soluble and a compound that remain in
a separate phase on the other hand, is insoluble. This then may provide an idea of the
possible identity of the compound. Based on the compounds solubility test, the group,
which the compound belonged to, was determined and was classified by group based on
characteristics.

INTRODUCTION
To be able to determine the identity of an organic compound, the qualitative analysis may be
used. Under qualitative analysis are solubility characteristics and functional group tests that give the
possible identity of a compound. Physical characteristics like melting point, boiling point, odor, color may
be helpful but classification of solubility of the compound may provide a general idea of its functional
group and general characteristic/s. (1) Solubility is the property of a solid, liquid, or gaseous chemical
substance called solute to dissolve in a solid, liquid, or gaseous solvent to form a homogeneous solution
of the solute in the solvent. It is important that the solubility of a solvent is known to identify compounds.
In this experiment, it shows the solubility of different organic compounds against the given solvents (
H 2 O , NaOH , NaHCO and HCl , that then confirms the solubility characteristics and
functional groups of the sample.
MATERIALS AND METHODS
Table 1. Reagents and Materials used
Reagents
H2O
5% NaOH
5% NaHCO3
HCl

Materials/Glasswares
Test tube/s
Graduated cylinder
Spatula
Dropper
Wash bottle and other cleaning materials

Table 1 shows the reagents and materials used in the experiment. Approximately 3 drops or 3mg
of compound 1 was obtained and added to 3mL of distilled water. It was then mixed and observed. It was
insoluble to distilled water thus new sample of compound 1 was obtained. The said compound was mixed
to 5% NaOH and found out to be insoluble as well. A new sample of compound 1 was obtained again and
mixed with HCl. It was still insoluble so it was classified as Group D. The same procedure was done with
compound 2 and it was found out to be insoluble with distilled water, soluble in 5% NaOH and insoluble in
5% NaHCO3. Therefore, it was classified as Group B 2. Compound 3 was then tested and resulted to
solubility in distilled water or H2O so it was classified as Group A. Lastly, compound 5 was mixed with
H2O. It was insoluble to the first reagent so new sample was obtained. It was insoluble in 5% NaOH so it
was mixed in HCl. It was then found out to be soluble so it was classified as Group C. Table 2 shows the
tabulation of resultsthe solubility and functional group of compounds 1-5.
Table 2. Solubility and Functional Groups of Compounds 1-5
Compounds

Observations (Solvent)

Compound 1
(Hexane, C6H14)
Compound 2
(Phenol, C6H6O)
Compound 3
(Acetone, C3H6O)
Compound 4
(Benzoic
Acid,
C7H6O2)
Compound 5
(Diphenylamine,
C12H11N)

Classification

H2O

5% NaOH

5% NaHCO3

HCl

Insoluble

Insoluble

N/A

Insoluble

Group D

Insoluble

Soluble

Insoluble

N/A

Group B2

Soluble

N/A

N/A

N/A

Group A

Insoluble

Soluble

Soluble

N/A

Group B1

Insoluble

Insoluble

N/A

Soluble

Group C

RESULTS AND DISCUSSION

Hexane (C6H14) is classified as Group D or hydrocarbons, alkyl halides, alcohols, aldehydes,
ketones with > 5 carbon atoms. Hexane is also insoluble in Water (H 2O), Sodium Hydroxide (NaOH), and
Hydrochloric Acid (HCl). Phenol (C6H60) is classified to Group B 2 or group of phenols, where it is
insoluble in Water (H2O), and Sodium Bicarbonate (NaHCO3) but is soluble in Sodium Hydroxide (NaOH).
Acetone (C3H6O) is classified as Group A, where it is soluble in Water (H 2O). It may be alcohols, ketones,
amines, and carboxylic acids with < 5 carbon atoms. Benzoic Acid (C 7H6O2) is classified as Group B1,
where it is insoluble in Water (H2O), but is soluble in Sodium Hydroxide (NaOH) and Sodium Bicarbonate
(NaHCO3). It may be carboxylic acids with more than 5 carbon atoms or belongs to phenols with electron
withdrawing groups. Lastly, Diphenylamine (C 12H11N) is classified as Group C or amines, where it is
insoluble in Water (H2O), and Sodium Hydroxide (NaOH) but is soluble in Hydrochloric Acid (HCl). The
following table shows the solubility classification with general characteristics of each group.
Table 3. Solubility Classification
Compound
1

Classification/Group
Group D

2
3

Group B2
Group A

Group B1

General Characteristics
hydrocarbons, alkyl halides, alcohols, aldehydes, ketones
with > 5 carbon atoms
phenols
may be alcohols, ketones, amines, and carboxylic acids with
< 5 carbon atoms
may be carboxylic acids with more than 5 carbon atoms

Group C

phenols with electron withdrawing groups

amines

Guide Questions:
1. Obtain from your instructor the list of organic compounds tested in the experiment. Based on how
you classified compounds 1-5, give the possible identity of the organic compounds.

Compound 1 (Hexane) identified as Group D, a group of Hydrocarbons, alkyl halides,

alcohol, aldehydes, ketones with > 5 carbon atoms
Compound 2 (Phenol) identified as Group B2, a group of Phenols.
Compound 3 (Acetone) identified as Group A, a group of alcohol, ketones, amines,
carboxylic acids with < 5 carbon atoms
Compound 4 (Benzoic Acid) identified as Group B1, a group of carboxylic acid with > 5
carbon atoms.
Compound 5 (Diphenylamine) identified as Group C, a group of amines.

CH

2. Write the structures of compounds 1-5. Explain how each compound dissolved in the specific
3
solvents used in the experiment. Whenever necessary,
support your explanation with the
chemical equation.

H3C

Compound 1 (Hexane, C6H14)

OH
-This compound is classified as Group D, where it is insoluble in Water (H 2O), Sodium
Hydroxide (NaOH), and Hydrochloric Acid (HCl).

Compound 2 (Phenol,C6H6O)

-This compound is classified as Group B2, where it is insoluble in Water (H2O), and
Sodium Bicarbonate (NaHCO3) but is soluble in Sodium Hydroxide (NaOH).

Compound 3 (Acetone, C3H6O)

-This compound is classified as Group A, where it is soluble in Water (H 2O).

Compound 4 (Benzoic Acid, C7H6O2)

-This compound is classified as Group B 1, where it is insoluble in Water (H 2O), but is

soluble in Sodium Hydroxide (NaOH) and Sodium Bicarbonate (NaHCO 3).

Compound 5 (Diphenylamine, C12H11N)

-This compound is classified as Group C, where it is insoluble in Water (H 2O), and

Sodium Hydroxide (NaOH) but is soluble in Hydrochloric Acid (HCl).

3. What other solvents maybe used to further narrow down the classification of organic compounds
based on solubility. Discuss each.
Ether (C2H5)2O can be used to determine the solubility of Water (H2O)
Concentrated Sulfuric Acid (H2SO4) can be used to determine the solubility of Hexane
(C6H14)
85% of Phosphoric Acid (H3PO4) - can be used to determine the solubility of Ethanol
(C2H6O).

CONCLUSION AND RECOMMENDATION

We therefore conclude that there are multitude of methods and qualitative analysis that we can
use to determine in what group a certain compound belongs. One of this qualitative analysis is the
solubility characteristics where we used some solvents to dilute compounds and see if theyre soluble or
insoluble with that solvent and then classify whether to what group they belong. So in this experiment we
can conclude that various compounds possess different solubility characteristics, which make them
divergent to one another and have a distinct reaction to a solvent.
We can recommend to the next people who will be conducting this kind of experiment to use
other solvents such as Ether (C 2H5)2O, Concentrated Sulfuric Acid (H 2SO4), 85% of Phosphoric Acid
(H3PO4) and others of the kind to determine the solubility of a certain compound. I also suggest that they
should manipulate more compounds to be tested so that they may have various and better results.

REFERENCES
(1) Gajjar, A.; Savjani, J.; Savjani, K. Drug Solubility: Importance and Enhancement Techniques. ISRN
Pharmaceutics. 2012.RetrievedAugust 2016 from http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3399483/