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Experiment 7: Solubility Classification

Festin, Aegina Joy M.


Raquepo, Veronica V.

WAD1, Group 7, Maam Noime Walican


February 8, 2014

I.

ABSTRACT

Determining the solubility of an organic compound is very important key as it can provide useful
information regarding the composition of the compound. In this experiment, the solubility of each of the
thirteen samples alanine, aniline, benzamide, benzoic acid, chlorobenzene, cyclohexane, ethylamine,
ethylacetate, hexane, -naphtol, phenol, salicylic acid and sulfanilic acid was evaluated using different
solvent systems. Seven solvent samples water, 5% NaOH, 5% HCL, 5% NAHCO 3, ether, concentrated
H2SO4 and 85% H3PO4, were used and the extent of dissolution of the samples were noted as +++ for
completely soluble, ++ for partially soluble, + for slightly soluble, and X for insoluble.
II.

III.

Keywords: miscibility, dissolution, solubility, solubility classification, solute, solvation, solvent

INTRODUCTION

The solubility of a substance pertains to the


amount of a given substance that will dissolve in a
given solvent. If more than 0.1 g of that substance
dissolves in 100 mL solvent, that sample is
soluble, and if less than 0.1 g dissolves, it is
insoluble. The solute is the one to be dissolved
and the solvent is the base substance. Miscibility
is also encountered in this topic. A miscible
substance is soluble with no limits while
immiscible shares the same meaning with
insoluble.
Breaking and reintroducing attractive forces
between the solute and solvent particles is the
dissolving process also known as solvation.
Solubility in general follows the like dissolves
like rule wherein polar solutes dissolve in polar
solvents and nonpolar solutes dissolve in
nonpolar solvents.
There are many factors that affect the
solubility of a compound. 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.
The students must be able to identify at the
end of the experiment the solubility, and the
acidity and basicity of the different organic
compounds
sampled
(alanine,
aniline,
benzamide,
benzoic
acid,
chlorobenzene,
cyclohexane, ethylamine, ethylacetate, hexane,

-naphtol, phenol, salicylic acid and sulfanilic


acid).
A comprehensive understanding of the
solubility of compounds is particularly needed
when it comes to the determination of unknowns
in the laboratory. It is also fundamental not only in
many scientific disciplines but also in numerous
practical applications such as the use of
medicine, transport of pollutants, food science,
and the field of pharmaceutics.

IV. EXPERIMENTAL
5-mL test tubes were used as container
for the solutions.
The samples whose solubility will be
determined were alanine, aniline, benzamide,
benzoic acid, chlorobenzene, cyclohexane,
ethylamine, ethylacetate, hexane, -naphtol,
phenol, salicylic acid and sulfanilic acid. The
solvent samples used were water, 5% NaOH, 5%
HCL, 5% NAHCO3, ether, concentrated H2SO4
and 85% H3PO4.
About 30 mg of each of the solid samples
were used and the solubility of each was
evaluated by adding 20 drops of the solvent.
As for the liquid samples, 2 drops of the
liquid sample were placed in respective test tubes
and 20 drops of the solvent were added.

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Chem 31.1 Solubility Classification
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V. Results
S
A
M
P
L
E

SOLVENT SYSTEM

H2
O

Ethe
r

5%
NaO
H

5%
NaHC
O3

5%
HCl

C
L
A
S
S
Conc
.
H2SO

85%
H3PO
4

++
+
X

++

10

11

12

13

++

++

S2

++
+
++

++
+
X

+++

++

++

+++

+++

++
+
++
+
++
+
++
+
++
+
++
+
++
+
++
+
++
+
+

+++

+++

++

A1

++

+++

+++

++

++

++

++

++

++

+++

++

++

+++

+++

++

+++

+++

++

Table 1. Experimental results of the


solubility tests (1 alanine, 2 aniline, 3
benzamide, 4 benzoic acid, 5
chlorobenzene, 6 cyclohexane, 7
ethylamine, 8 ethylacetate, 9 hexane,
10 -naphtol, 11-phenol, 12-salicylic acid, 13

concentrated sulfuric acid and 85% H3PO4. 1) The


presence of a functional group can be
detected. For instance, because hydrocarbons
are insoluble in water, the mere fact that an
unknown is partially soluble in water indicates
that a polar functional group is present. 2)
Solubility in certain solvents gives more
specific information about the functional
groups. For example, benzoic acid is insoluble
in a polar solvent, water, but is converted by
5% sodium hydroxide solution to a salt, sodium
benzoate, which is readily water soluble. In this
case, then,

the solubility in 5% sodium hydroxide solution


of a water insoluble unknown is a strong
indication of an acidic functional group. 3)
I
Deductions about molecular size and
composition can also sometimes be made. For
SB
example, in many homologous series of
SN
monofunctional compounds, the members with
fewer than about five carbon atoms are water
I
soluble, whereas the higher homologs are
insoluble. In these tests, compounds that
AW
dissolve to the extent of about 30mg per 1 mL
of the solvent are considered soluble. Some
AW
textbooks consider 33 mg of solute per 1 mL of
solvent as the standard.
A1
Since most organic molecules have both a
polar and a nonpolar entity, it can be deduced
A2
that its solubility would depend on the balance
between the two parts. As the percentage of the
hydrocarbon portion increases while the polar part
remains unchanged, the solubility in polar solvent
decreases while that in nonpolar solvent
increases.

sulfanilic acid)

The results based on the extent of dissolution


of each sample in different solvent systems were
tabulated using the following notations: +++ =
completely soluble; ++ = partially soluble; + =
slightly soluble; and X = soluble. The solubility
classes are detailed in Table 2 in the Appendix,
including the symbols used in Table 1.
VI. Discussion
The solubility of a substance is a measure of
the equilibrium between the substance in its solid
state and the substance, or its ions, in solution. It
can also be defined as the maximum amount of
solute that can be dissolved in a fixed amount of
solvent at a specific temperature.
There are three kinds of information that can
often be obtained about an unknown substance
by a study of its solubilities in water, 5% sodium
hydroxide solution, 5% sodium bicarbonate
solution, 5% hydrochloric acid solution, cold

The solubility behavior of a compound can be


used to place it into one of the solubility classes,
namely S1, S2, SA, SB, A1, A2, B, MN, N and I.
Different solvents are used to identify an unknown
compound; the most common are listed below
with their corresponding effects on compounds.
1. Water
This is a polar solvent which dissolves polar
compounds. Several structural features of the
unknown can be deduced if it is water-soluble. It
must be of low molar mass and will usually
contain no more than four to five carbon atoms,
unless it is polyfunctional. It must contain a polar
group that will form a hydrogen bond with water,
such as the hydroxy group of an alcohol or a
carboxylic acid, the amino functionality of an
amine, or the carbonyl group of aldehydes or
ketones. Esters, amides, and nitriles dissolve to a
lesser extent, and acid chlorides or anhydrides
react with water rather than simply dissolving in it.

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Chem 31.1 Solubility Classification
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On the other hand, alkanes, alkenes, alkynes,


and alkyl halides are water-insoluble.
The borderline for water solubility of
monofunctional organic compounds is most
commonly at or near the member of the
homologous series containing five carbon atoms.
Thus, butanoic acid is soluble, pentanoic acid is
borderline, and hexanoic acid is insoluble in
water.
2. Diethyl Ether
Diethyl ether is a nonpolar solvent that is
used to determine whether the water-soluble
substance is extremely polar. If it is, then it cannot
be dissolved in ether. Examples are salts of
organic acids, amine hydrochlorides, amino acids
and polyfunctional compounds with hydrophilic
functional groups. If it is soluble, then it is said to
be organic because the hydrocarbon portion
interacts with ether, however small. The acidity of
those that are ether soluble is tested using litmus
paper. Compounds that turn blue litmus into red
are acidic and are most likely carboxylic acids;
those that turn red litmus paper into blue are
amines; and those that are neutral are usually
alcohols.
3. 5% Sodium Hydroxide
Compounds dissolve in aqueous base
solutions because they form sodium salts that are
soluble in aqueous medium. However, the salts of
some high molecular weight compounds are not
soluble and will precipitate out.
Both phenols and carboxylic acids produce
resonance stabilized conjugate bases. In phenols,
substitution of an electron withdrawing group
(nitro or cyano) at the ortho and para positions of
the ring increases the acidity. Phenols with two or
three nitro groups at the ortho and para positions
are strong acids that will dissolve in both strong
and weak bases.
Carboxylic acids, which are strong acids, and
phenols, which are weak acids, dissolve in
sodium hydroxide because they are converted
into their water-soluble sodium salts.

4. 5% Sodium Bicarbonate

strong acids from weak acids. Strong acids can


easily be deprotonated and can attack even a
weak base such as sodium bicarbonate, so they
are soluble in this solvent. Weak acids, unlike the
strong ones, do not react with weak bases.

5. 5 % HCl

If the compound is soluble in HCl but


insoluble in water, an amine should be considered
immediately. Aliphatic amines (RNH2, R2NH,
R3N) are basic compounds which readily dissolve
in acid because they form hydrochloride salts that
are soluble in aqueous medium.

6. Concentrated H2SO4
Concentrated sulfuric acid protonates all
organic compounds that contain oxygen and/or
nitrogen, as well as alkenes and a few aromatic
hydrocarbons.
These
protonated
organic
compounds exist as ionic salts in sulfuric acid.
Because sulfuric acid is a highly polar liquid, it
dissolves the protonated compounds. The
dissolution of compounds in H2SO4 may also
produce large amounts of heat and/or a change in
the color of the solution. For example, an alkene
adds the elements of sulfuric acid to form an alkyl
hydrogen sulfate that is soluble in the acid, and an
oxygen-containing compound becomes protonated
in concentrated acid to form a soluble oxonium
salt.
Substances that exhibit this solubility
behavior are termed neutral compounds.

Compounds which are insoluble in sulfuric


acid are extremely weak bases. It is the extreme
acidity of concentrated sulfuric acid along with its
powerful ionizing ability that allows these
compounds to be soluble in sulfuric acid. Thus
sulfuric acid is able to protonate alcohols, ketones
aldehydes,ester an unsaturated hydrocarbons.
The resulting ions produced are soluble in the
medium.

When a compound is insoluble in water but


soluble in NaOH, it is either a weak or a strong
acid. Testing its [unknowns] solubility in sodium
bicarbonate (pKa=10.3), which is less basic than
sodium hydroxide (pKa=13.8) will differentiate

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Chem 31.1 Solubility Classification
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Ionizing power of conc. H2SO4

Figure 1. Classification of organic


compounds by solubility

7. 85% Phosporic Acid


Phosphoric acid, on the other hand is not
nearly as strong an ionizing solvent as is sulfuric
acid. It is capable of ionizing most of the oxygen
containing
compounds
such
as
alcohols,aldehydes, and esters, but is not able to
ionize unsaturated hydrocarbons such as
alkenes,alkynes or aromatics. Thus these
compounds will be insoluble in this medium.
VII. Conclusion and Recommendations
The solubility behavior of a compound is
affected by the nature of solvent. This very idea is
used to identify the structure of an unknown
compound among other tests. The solubility of an
organic compound in water, dilute acid, or dilute
base can provide useful, but not definitive,
information about the presence or absence of
certain functional groups. In reality, however, the
assignment of an unknown to a formal solubility
class may be arbitrary because a large number of
compounds exhibit borderline behavior.
It is often possible to predict the solubility
class of a particular compound solely by
reference to its structural formula, there are many
cases where this would result in an incorrect
prediction.
Upon shaking, when two colorless liquid
phases lie one above the other, it is often possible
to overlook the boundary between them and thus
to see only one phase. This mistake can generally
be avoided by shaking the test tube vigorously
when a liquid unknown seems to have dissolved
in the solvent. If two phases are present, the
solution will become cloudy.
VIII. Appendix

IX. References:
Table 2. Organic compounds comprising the
solubility classes

Chemistry Online. (n.d.). Solubility. Retrieved


March
9,
2013
from

http://webapps.utsc.utoronto.ca/che
mistryonline/solubility.php
Clayden J. (2001). Organic Chemistry. Oxford
University Press
Gilbert, J. (2011).Experimental Organic
Chemistry: A Miniscale and Microscale Approach.
Boston, MA: Cengage Learning
Lehman, J. (2008) Operational Organic
Chemistry: A Problem-Solving Approach to the
Laboratory Course. Prentice Hall
Shriner, R. (2004). The Systematic Identification
of Organic Compounds. Canada: John Wiley &
Sons.

I hereby certify that I have


substantial contribution to this report.

given

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Chem 31.1 Solubility Classification
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_______________________
Festin, Aegina Joy M.

_______________________
Raquepo, Veronica V.

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Chem 31.1 Solubility Classification
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