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 Several reagents were given for the
advanced methods such as using attributes like experiment. The reagents dissolved were
melting point, it is still useful. Solubility depends alanine, aniline, benzanamide, benzoic acid,
on several factors such as the nature of solute chlorobenzene, cyclohexane, ethylamine, ethyl
and solvent, temperature, and pressure. acetate, hexane, E-naphthol, phenol, salicylic
Solubility tests can be considered crude acid, and sulfanilic acid. The solvents used were
because functional groups react differently on distilled water, ether, 5% NaOH, 5%NaHCO3,
various substances. The concept of polarity and 5% HCl, and concentrated sulfuric acid. Twenty
pH will be greatly used throughout the drops of the liquid samples and/or 5 g of the
experiment. The compounds to be tested will solid samples were used per 4 ml of solvent.
encounter several solvents to determine their The mixtures were placed in 5 ml test tubes.
solubility in each. A guide will be used to classify After the experiment, the results were tallied and
each compound and the results will be 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

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