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Names: Balo, Marielle Date Performed: 30 Jan 2017

Deseo, Ma. Rogemae Date Submitted: 09 Feb 2017


Gerolaga, Winston Jake
Group: 4

Experiment No. 1

Solubility Behavior of Organic Compounds

I. Introduction

The strength of a compounds intermolecular forces determines many of its physical


properties, including its boiling point, melting point, and solubility. Solubility is the extent
to which a compound, called the solute, dissolves in a liquid, called the solvent.
Compounds dissolve in solvents having similar kinds of intermolecular forces (Smith,
2011). The compounds nature or polarity hugely affects its solubility as well as the
temperature, molecular weight, acidity or basicity of the compound, intermolecular
forces of attraction, structure of the compound, and pressure.

Generally, this experiment aims to test the solubility of representative organic


compounds in different solvents. Specifically, this aims to classify the given compounds
into different solubility classes. This also aims to relate the solubility of an organic
compound with its structure.

II. Methodology

In this experiment, the procedures from the laboratory manual were all followed.

The solubility of the organic compound samples were determined using different
solvents. Acetone, benzoic acid, phenol, aniline, benzamide, tert-butyl chloride, benzyl
alcohol, ethyl alcohol, toluene, benzaldehyde hexane, and sucrose were the organic
compounds used in this experiment. Additionally, the solvents used in this experiment
are distilled water, 5% NaOH, ether, 5% HCl, 5% NaHCO3 and concentrated H2SO4.

Five drops of distilled water, the first solvent used, was placed into twelve test tubes.
For each of the test compounds, 1-2 drops or a pinch was added into one of the test
tubes. Samples were shaken vigorously and recorded as soluble or insoluble.

For water-soluble compounds, required amount of the fresh sample into 5 drops of
ether were added to check if the compounds were also ether-soluble. Ether-soluble
compound belong to S1 group, and ether-insoluble compounds belong to S2 group.

The solubility of water-insoluble compounds were tested first using 5% sodium


hydroxide (NaOH) solution. For NaOH-soluble compounds, solubility with 5% sodium
bicarbonate (NaHCO3) solution was also tested using a fresh sample of the compound.
NaHCO3-soluble compounds were classified as A1, and NaHCO3-insoluble compounds
were classified as A2.

For NaOH-insoluble compounds, solubility with 5% hydrochloric acid (HCl) solution


was tested using a fresh sample compound. Basic compounds (B) were insoluble in 5%
HCl; miscellaneous neutral compound (M) were insoluble in HCl and contains N or S.
The solubility in concentrated sulfuric acid (H2SO4) of the compounds that did not
contain N or S were determined, and classified as inert compound (I) for
H2SO4-insoluble compounds and neutral compound (N) for H2SO4-soluble compounds.

III. Results and Discussion

Solubility tests are essential to determine the functional group of an organic


compound. In this experiment; however, the relationship of the solubility of the known
compound from a certain functional group with its structure and chemical properties are
focused.
Basically, the energy needed to break up the interactions between the molecules or
ions of the solute comes from new interactions between the solute and the solvent.
Structures of molecules can affect their solubility.

Solubility of different samples were classified based on the observations made on


the mixtures. Acetone, ethyl alcohol, hexane, tert-butyl chloride, and sucrose are all
soluble in water and ether (Table 1). Most of them contain less than four carbons and
some polar groups of oxygen which increased their solubility. Toluene is soluble only in 5%
hydrochloric acid, therefore it was classified as a basic compound. Phenol, a weak acid,
is only soluble in 5% sodium hydroxide hence it belongs to the NaHCO 3-insoluble
classification (A2). Aniline and benzamide, although slightly soluble, were considered as
miscellaneous neutral compounds since they remained insoluble in 5% hydrochloric
acid. In the case of aniline, the presence of nitrogen reduced the basicity of the
compound affecting the protonation and solubility. However, benzamide can also be
considered as a basic compound just like toluene because it slightly dissolved in 5%
hydrochloric acid. Benzoic acid is soluble in concentrated sulfuric acid, therefore it is a
neutral compound. Finally, benzaldehyde and benzyl alcohol are both inert compounds
because the two substances remained insoluble in concentrated sulfuric acid.

Uniformity in the solution and absence of precipitates, colloidal suspensions and,


separations or the formation of layers were observed in soluble compounds. Presence
of precipitate and fluid separation indicated insolubility.

According to Smith (2011), most ionic compounds are soluble in water, but are
insoluble in organic solvents. If an organic compound contains one polar functional
capable of hydrogen bonding with the solvent for every five C atoms it contains, it is
considered as water-soluble only. Water-soluble organic compound has an O- or
N-containing functional group that solubilizes its nonpolar carbon backbone.

The presence of a polyfunctional group is indicated by a partially soluble sample,


since hydrocarbons are insoluble in water. The solubility in 5% sodium hydroxide
solution of a water insoluble sample is a strong indication of an acidic functional group.
Deductions about molecular size and composition can also sometimes be made.
Members with fewer than about five carbon atoms are water soluble, whereas the higher
homologs are insoluble, in cases of homologous series of monofunctional compounds.

The solvents involved in the experiment have distinct properties from one another.
Water is a polar solvent which dissolves polar compounds. Diethyl ether is a nonpolar
solvent which is used to determine whether the water-soluble substance is extremely
polar. Compounds dissolve in aqueous base solutions because they form sodium salts
that are soluble in aqueous medium. Furthermore, these compounds solubility in
sodium bicarbonate, which is less basic than sodium hydroxide differentiates strong
acids from weak acids. Basic compounds like aliphatic amines readily dissolve in acid
because they form hydrochloride salts that are soluble in aqueous medium.
Concentrated sulfuric acid protonates all organic compounds that contain oxygen and/or
nitrogen, as well as alkenes and a few aromatic hydrocarbons. These protonated
compounds are then dissolved because sulfuric acid is a highly polar liquid.

The dissolution of compounds in H2SO4 can produce large amounts of heat and/or a
change in the color of the solution. Based on the observations made, benzaldehyde,
turned into a dark orange H2SO4 -soluble solution. Benzoic acid was partially dissolved.
Benzyl alcohol, on the other hand, formed a cloudy light orange H 2SO4-insoluble
solution.

5% 5% Conc. Solubility
Compound Structure H2O ether 5% HCl
NaOH NaHCO3 H2SO4 Class

Acetone
Ether-soluble
(C3H6O) Soluble Soluble
(S1)
Aniline Miscellaneous
Neutral
(C6H5NH2) Insoluble Insoluble Insoluble
Compound
(M)

Benzyl
alcohol
Inert
(C6H5CH2O Insoluble Insoluble
Compound (I)
H)

Benzaldehy H2SO4 -
de soluble
Insoluble Insoluble Soluble Neutral
(C7H6O)
Compound
(N)

H2SO4 -
Benzoic acid soluble
Slightly
(C6H5COOH Insoluble Insoluble Neutral
Soluble
) Compound
(N)

Benzamide Slightly Basic


Insoluble Insoluble
(C7H7NO) Soluble Compound (B)

Ethyl alcohol Ether-soluble


Soluble Soluble
(C2H5OH) (S1)

Hexane Ether-soluble
Soluble Soluble
(C6H14) (S1)
Phenol NaHCO3 -
Insoluble Soluble Insoluble
(C6H5OH) insoluble (A2)

Tert-butyl
Ether-soluble
chloride Soluble Soluble
(S1)
(C4H9Cl)

HCl-soluble
Toluene
Insoluble Insoluble Soluble Basic
(C7H8)
Compound (B)

Sucrose Ether-soluble
Soluble Soluble
(C12H22O11) (S1)

Table 1. Solubility classes of the samples.

IV. Conclusion and Recommendations

Therefore, the nature of the solvent affects the solubility behavior of the sample. The
structural formula of the sample has also a significant effect to its solubility. The
presence or absence of functional groups of which the compound belongs to can be
determined based on the solubility of the compound in the water, dilute acid, or dilute
base. Moreover, the structure and polarity of organic compounds are important in
determining the solubility and that solubility is a vital thing to know when handling
organic compounds.

Some observations did not match the expected outcomes based on the existing
theories and past experiments. The inconsistencies might be due to the excessive
additions of samples or the mixtures were not shaken thoroughly. In addition, the
verdicts for the solubility of the mixtures could be influenced by erroneous assessment
done by the researchers.
V. References

Cepeda, R., et.al. (2015, April 2). Solubility Behavior of Organic Compounds. Retrieved
from
https://www.scribd.com/document/260697271/Solubility-Behavior-of-Organic-Co
mpounds

Miranda M. & Ogario, J.P. (2014, July 31). Preliminary Tests and Solubility Classification
of Organic Compounds. Retrieved from
https://www.academia.edu/10879682/Preliminary_Tests_and_Solubility_Classific
ation_of_Organic_Compounds

Smith J.G. (2011). Organic Chemistry (3rd Ed.). The McGraw-Hill Companies, Inc., 1221
Avenue of the Americas, New York, NY 10020.