Experiment 7- Solubility Classification Group 7, Chem 31.1, AB2, Mr.

Kevin Sison
Atienza, Von Ervy; Alcantara, Mark Jun May 12, 2010

ABSTRACT

Organic substances have different solubility classes. Each class has certain characteristics
unique to it. Determination of the solubility class of different organic substances will help give information
regarding which functional groups were present on it, as well as other characteristics of the compound.
The experiment involves the use of different solvents to test various organic compounds. The solvents
used were distilled water, ether, 5% NaOH, 5%NaHCO3, 5% HCl, and concentrated sulfuric acid. A test
using litmus paper is also used. The substances were then classified using a dichotomous key diagram.
From the results, it can be inferred that certain functional groups dissolve in certain solvents only. This
information is necessary for compound identification.

KEYWORDS: solubility, organic compounds, polarity, solvent system, solubility classification

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tabulated. The information gained will help in

INTRODUCTION identifying other properties of the compounds.

Solubility is one method used to identify the EXPERIMENTAL

presence of certain functional groups in a
compound. Though it is not as accurate as other
advanced methods such as using attributes like
melting point, it is still useful. Solubility depends
on several factors such as the nature of solute
and solvent, temperature, and pressure.
Solubility tests can be considered crude
because functional groups react differently on
various substances. The concept of polarity and
pH will be greatly used throughout the
experiment. The compounds to be tested will
encounter several solvents to determine their
solubility in each. A guide will be used to classify
each compound and the results will be
Several reagents were given for the
experiment. The reagents dissolved were
alanine, aniline, benzanamide, benzoic acid,
chlorobenzene, cyclohexane, ethylamine, ethyl
acetate, hexane, E-naphthol, phenol, salicylic
acid, and sulfanilic acid. The solvents used were
distilled water, ether, 5% NaOH, 5%NaHCO3,
5% HCl, and concentrated sulfuric acid. Twenty
drops of the liquid samples and/or 5 g of the
solid samples were used per 4 ml of solvent.
The mixtures were placed in 5 ml test tubes.
After the experiment, the results were tallied and
classified according to a dichotomous key (see
Appendix 2).

RESULTS

The results were tabulated and classified has undergone a test for a specific solvent. The
according to a dichotomous key. The key solutes were then classified into groups which
indicates the path to be followed once a solute they share the same solubility properties.

Sample Water Ethe Litmus 5% 5% 5% H2SO4 Cla

r (R/B/un. NaOH NaCO3 HCl (Conc. ss
) )
Alanine # x - - - - - S2
Aniline x - - x - # - B
Benzamide x - - x - x # N
Benzoic Acid x - - # # - - A1
Chlorobenzen x - - x - x x I
e
Cyclohexane x - - x - x x I
Ethylamine # # B - - - - So
Ethylacetate # # Un. - - - - S1
Hexane x - - x - x x I
E-naphtol x - - # x - - A2
Phenol x - - # x - - A2
Salicylic Acid x - - # # - - A1
Sulfanilic x - - # # - - A1
Acid

DISCUSSIONS groups may form polar bonds or induce polarity

The solubility of a solute is the
maximum quantity of solute that can dissolve in
a certain quantity of solvent or quantity of
solution at a specified temperature. Certain
factors affect the solubility of a compound in a
specific solvent or quantity of solution like the
nature of the solute and solvent, melting point,
molecular weight and the presence and position
of the functional groups present in the
compound.
Like dissolves like. Most organic
compounds have both polar and non-polar parts,
so the solubility of these compounds in certain
solvents depends on the balance of the polar
and non-polar parts of the compound. As the
hydrocarbon portion of the increases, the more
non-polar it becomes; the less soluble in water
and the more soluble in a non-polar solvent it
will be.
Generally, solubility of organic
compounds is inversely proportional to its
melting point meaning the higher the melting
point of the compound, the harder it will be to
dissolve the compound.
Molecular weight is another
factor. An increase in molecular
weight leads to the increase in the
intermolecular forces of attraction (in
a solid) which will then lead to a
decrease in solubility.
Usually, compounds that have branches
are more soluble than a corresponding straight
chain compound without branches. This is
because branches lowers intermolecular forces
and thereby decreases intermolecular attraction.
The presence of functional groups also
affects solubility of compounds. These functional
in a molecule. Functional groups also give
information on the acidity of the compound.
Acidity of the substance tells whether the
substance will dissolve or not in basic or acidic
solvents/solutions. The trend is that strong acids
are soluble in strong and weak bases/basic
solutions while weak acids dissolve only in
strong bases/basic solutions.
Water as a solvent
• Water is a poor solvent for
hydrocarbons.
• Presence of double bonds, triple bonds
or aromatic rings does not affect the
polarity greatly –similar to alkanes in
their solubility.
• Substituting halogen for hydrogen
decreases the water solubility.
• Salts are extremely polar and are
usually water soluble.
• Acids and amines are more soluble than
nonpolar compounds (due to H-
bonding).
• Solubility of amines decreases as the
basicity decreases.
• Many tertiary amines are more soluble
in cold than in hot water (at lower
temperatures, the solubility of the
hydrates is involved).
Solubility in Water
In general, most organic compounds
that have no more than six carbon atoms are
soluble in water. However, there is an indefinite
borderline with respect to the solubility of carbon
compounds in distilled water. For example, a
few six-carbon alcohols, such as cyclohexanol,
are soluble in water even if it is said that
alcohols are water-soluble only if they have
fewer than six carbons. The same kind of
borderline solubility is to be found among all
functional-group classes whose low molecular
weight members are soluble in water.
Multifunctional compounds, for example,
polyhydroxy compounds such as carbohydrates,
are often very soluble in water. Solubility
depends on the exact structure of a compound,
not only on the number of carbon atoms that it
contains, and it is necessary to interpret
solubility characteristics cautiously.
Solubility in Ether
Ether is a polar molecule wherein the
oxygen has a partial negative charge and each
carbon attached to it bears a partial positive
charge. Since the solubility behavior of water
soluble compounds gives no information about
the presence of acidic or basic functional
groups, their solubility in ether are first tested.
Compounds which are insoluble in ether are
automatically placed in class S. These
compounds are too polar to dissolve in ether,
such as salts of organic acids, amine
hydrochlorides, amino acids and polyfunctional
compounds with hydrophilic functional groups.
Acidity of the aqueous solutions of ether soluble
compounds is tested using litmus paper which
turns blue when pH is >8.3 and turns red when
pH is <4.5. Ether soluble compounds that turns
litmus paper to red is classified under Sa. Those
that turn the litmus paper to blue are under the
Sb classification and those that did not react
with the litmus, Sg.
Solubility in NaOH
Solubility of substance depends on its
pH level and on certain functional groups
present in the substances. Solubility of organic
compounds is a consequence of the presence of
acidic hydrogen which can be one bonded to O,
N, S, or even C. Organic acids, which are
insoluble in water, normally dissolve in a NaOH
solution. The pH of this solution is greater than
14, so any acid whose pKa < 12 is converted
almost entirely to its conjugate base. Thus,
water-insoluble carboxylic acids and phenols will
both dissolve in sodium hydroxide solution.
Esters with five or six carbon atoms that
are almost completely soluble in water may be
hydrolyzed by continued shaking with 5% NaOH
solution. The alkali should not be heated and the
solubility or insolubility should be recorded after
1-2 minutes.
Solubility in 5% NaHCO3:
When a compound is insoluble in water
but soluble in NaOH, a third solubility test using
5% sodium bicarbonate is called for. It was
stated earlier that a strong bases reacts readily
with strong and weak acids. That was what
happened in the NaOH test. Solubility in 5%
NaHCO3, a weak base, differentiates a strong
acid to a weak one since only the strong acids
are expected to react with NaHCO3. Sodium
bicarbonate is a weaker base than sodium
hydroxide; a 0.6 M NaHCO3 solution has a pH
of approximately 9. It dissolves a water insoluble
organic acid whose pKa is less than 7.5 by
converting it to a water-soluble salt. Whereas
carboxylic acids (pKa < 5) dissolve in a sodium
bicarbonate solution, most phenols do not but
those containing strong electronegative groups
which increase the acidity of phenol do.
Solubility in 5% HCl
The only organic compounds that are
insoluble in distilled water but soluble in dilute
hydrochloric acid solution are amines, the major
class of basic organic compound. Nearly all
amines undergo reaction with HCl to produce
ionic ammonium salts that are almost always
soluble in water. This behavior is the same for
tertiary (R3N), secondary (R3NH), and primary
(RNH2) amines. Solubility of amines in dilute
HCl is connected with the tendency of the lone
pair of electrons of N to bond with the proton,
resulting in salt formation. In general, aliphatic
amines are readily soluble in dilute HCl. When
alkyl groups are bulky such as in secondary and
tertiary amines, solubility in dilute HCl
decreases. This is a consequence of steric
inhibition of the approach of the acid to bond
with the lone pair or the instability of the salt
formed as a result of steric crowding.
Solubility in Concentrated H2SO4
Many compounds which are neutral
towards 5% HCl behave as bases in more acidic
solvents like concentrated H2SO4. Concentrated
H2SO4 is used with neutral, water insoluble
compounds containing no elements other than
C, H, and O. Solubility in or any other evidence
of a reaction with H2SO4 indicates the presence
of an oxygen atom or of a reactive hydrocarbon
function such as an olefinic bond or easily
sulfonated aromatic ring (class N).
Solubility depends on capability to
substance to undergo sulfonation. If the
substance is unsaturated or contains a
functional group with oxygen, it readily
dissolves.
If the compound is unsaturated, is
readily sulfonated, or posses a functional group
containing oxygen, it will dissolve in cold,
concentrated H2SO4. Alkanes, cycloalkanes, and
their halogen derivatives are insoluble in H2SO4.
Simple aromatic hydrocarbons, and their
halogen derivatives do not undergo sulfonation
and are insoluble in H2SO4. However, the
presence of two or more alkyl groups on the
aromatic ring permits the compound to be
sulfonated.
GUIDE QUESTIONS AND ANSWERS
1. Give the rationale behind the solubility
of the compounds in each class.
Sa = They are soluble in water and ether
because they contain both polar and non-polar
functional groups. They are red to litmus
because their pH is below 4.5.
Sb = They are soluble in water and ether
because they contain both polar and non-polar
functional groups. They are blue to li-tmus
because their Ph is above 8.3.
S1 = They are soluble in water and ether
because they contain both polar and non-polar
functional groups. They are neutral to litmus
because their pH fall within the range
4.5<pH<8.3.
S2= They are soluble in water but insoluble in
ether because they are too polar to dissolve in
the latter.
A1 = They are insoluble in water due to the
dominance of their non-polar groups. They are
soluble in 5% NaOH because they contain an
acidic functional group and in 5% NaHCO3
because their acidity is strong enough to react
with a weakly basic solvent.
A2 = They are insoluble in water due to the
dominance of their non-polar groups. They are
soluble in 5% NaOH because ether contains an
acidic functional group but are insoluble in 5%
NaHCO3 because their acidity is insufficient to
react with a weakly basic solvent.
B = They are insoluble in water due to the
dominance of their non-polar groups. They are
insoluble in 5% NaOH because they do not
contain an acidic functional group but are
soluble in 5% HCl due to their basicity in
aqueous solutions.
MN = They are insoluble in water due to the
dominance of their non-polar groups. They are
insoluble in 5% NaOH and 5% HCl because
they are neutral in aqueous acid or basic
solutions. Because they are S or N containing
compounds and therefore, have an atom with an
unshared pair of electrons, they are expected to
dissolve in concentrated H2SO4.
N = They are insoluble in water due to the
dominance of their non-polar groups. They are
insoluble in 5% NaOH and in 5% HCl because
they are neutral in aqueous acid or base
solutions. However, they behave as base in
more acidic solvents such as concentrated
H2SO4, thus they are soluble in the latter.
I = They are insoluble in water due to the
dominance of their non-polar groups. They are
insoluble in 5% NaOH and in 5% HCl because
they are neutral in aqueous acid or base
solutions. They are too weakly basic to dissolve
in concentrated H2SO4.
2. Complete the diagram. (See Appendix 1
and 2).
CONCLUSION
The solubility of the organic compounds
given is different for every solvent. They are
affected by the presence of functional groups
that react differently under various
circumstances. Also, the functional groups affect
the strength of the compound as well as its
polarity. Polar compounds such as ethylamine
dissolves in water, which confirms the concept
of ‘like dissolves like’.
References:
Classification of Organic Compounds by
Solubility. (n.d.). Retrieved from
http://opencourseware.kfupm.edu.sa/colleges/cs
/chem/chem303/files%5C3-
Lecture_Notes_CHEM-303_
%28Chapter_5%29.pdf &
http://bcs.whfreeman.com/mohrig2e/content/cat
_010/techniques.pdf.
I hereby certify that I have given substantial
contribution to this report.
 _________ _______________
Von Atienza Mark Jun Alcantara
Appendix: Solubility Classification
Appendix 1: Solubility Classes

Appendix 2: Dichotomous key for classification (Organic Qualitative Analysis)