Experiment #7: Solubility Classification

Alexis Albarico
Mae Bojare
Shaliza Hernandez
Group 7, Chem 31.1, SAD2, Mr. Zaragoza
Jan. 29, 2011

I. Introduction

Solvation or the dissolving process involves breaking and reestablishing or attractive forces
between solute and solvent particles. Furthermore, solubility is defined as the amount of solute that can
dissolve in a certain amount of solvent at a certain temperature. It is generally governed by the principle
“like dissolves like.” This means that polar solutes dissolve in polar solvents, likewise, nonpolar solutes
dissolve in nonpolar solvents. The solubility of a compound is determined by many factors. It is primarily
affected by the compounds’ nature/polarity but it is also affected by temperature, molecular weight,
structure of the compound, acidity or basicity of the compound, intermolecular forces of attraction, and the
over-all pressure aids in the dissolution of the solute in the solvent.
At the end of this experiment, students should be able to determine the solubility, along with the
acidity and basicity, of different organic compounds, namely: alanine, aniline, benzamide, benzoic acid,
chlorobenzene, cyclohexane, ethylacetate, hexane, E-/α-napththol, dimethylamine, phenol, salicylic acid,
and sullfanic acid.
Knowledge in the solubility of compounds is chiefly used in identification and analysis of
unknowns usually handled in laboratories. It also helps in giving important information on the structural
composition of a given compound, which is especially useful in the field of Organic Chemistry. Better
understanding of the behavior of different compounds would be beneficial for experiments and studies in
the future.

II. Methods

Using the solubility diagram and results table provided, the students determined the different
solubility classification of the following sample solutes: alanine, aniline, benzamide, benzoic acid,
chlorobenzene, cyclohexane, ethylacetate, hexane, E-/α-napththol, dimethylamine, phenol, salicylic acid,
and sulfanilic acid. The solvents to be used in this experiment are the following: water, ether, litmus (to
determine the acidity/basicity), 5% NaOH, 5% NaHCO3, 5% HCl, and concentrated H2SO4.

One (1) drop of liquid sample or 5mg of powdered solid sample was dissolved in 0.2mL solvent.
The solubility tests were done in 5mL test tubes.
III. Results and Discussion

Different solvents have different roles in the solubility classification of organic compounds. The
solvents used in this experiment are water, ether, sodium hydroxide, sodium bicarbonate, hydrochloric
acid, and sulfuric acid. Water classifies compounds soluble to it as polar and nonpolar if it is otherwise.
Ether classifies compounds as acidic, basic, and neutral. Sodium hydroxide classifies compounds soluble
to it as acids. Sodium bicarbonate classifies soluble compounds as strong acids and weak acids if it is
otherwise. On the other hand, hydrochloric acid classifies compounds soluble to as bases. Lastly, sulfuric
acid classifies compounds soluble to it as neutral and those insoluble are inert. With these being said,
organic compounds therefore can be divided into ten groups.

The first group would be the SA group or the water-soluble acid group. They are partly polar which
makes them soluble to both water and ether. Also, they turn blue litmus to red. The next is the S B or the
water-soluble base group. They are electron pair donors and they turn red litmus to blue. In the
experiment, the solute methylamine* is a member of this group. S N or water-soluble neutral group are
monofunctional alcohols, aldehydes, ketones, esters, nitriles and amides which are partially polar and
they are soluble in water and ether. An example of this in the experiment is the solute ethylacetate. S 2 or
ether-insoluble group consists of polar compounds which include amine salts, carboxylic acid salts,
polyhydroxy alcohols, polycarboxylic acids, hydroxy acids, amino acids, and carbohydrates. An example
of this is the alanine, an alpha amino acid. AS or strong acidic group has members that are strong proton
donors. They are insoluble to water but soluble to 5% NaOH and 5% NaHCO 3 and the reaction yields a
water-soluble salt. The members of this group are carboxylic acids, sulfonic acids, polyhalide nitro group
and aldehyde group substituted phenols, and electron-withdrawing group (ortho and/or para position)
substituted phenols and examples of this group in the experiment are benzoic acid, salicylic acid, and
sulfanilic acid. They are insoluble in water because of the presence of benzene rings in these
compounds. AW or weak acidic compounds include phenols, enols, primary and secondary nitro
compounds, and sulfonamides of primary amines. They are soluble in 5% NaOH but insoluble to both
water and 5%NaHCO3 and in the experiment phenol and E-/α-naphthol belong to the A 2 group. The B or
basic group has members that are electron pair donors that form hydroxide anions in aqueous solutions.
This group includes primary, secondary, tertiary amines except diary and triaryl amines, hydrazines, and
some N,N-dialkyl-carboxamides. In the experiment, aniline is an example and it is insoluble in water
because of the presence of a benzene ring. The NM or miscellaneous neutral group compounds contain
sulfur and nitrogen such as aromatic nitro compounds, nitriles, amides, and sulfanomides of secondary
amines. Benzamide is a member of this group and it is insoluble in water, 5% NaOH, and 5% NaHCO3.
The N or neutral group compounds are mostly containing oxygen and lacks sulfur or nitrogen. Members
of this group include alcohols, aldehydes, anhydrides, esters, ethers, ketones, and unsaturated
hydrocarbons. Lastly, the I or inert group compounds include alkyl and aryl hydrocarbons, saturated
 hydrocarbons, and diaryl ether. Chlorobenzene, cyclohexane and hexane represent this group in the
experiment.

Table 1: Solubility of Different Solutes and Solvents

Water Ether Litmus 5% NaOH 5% 5% HCl Conc.

NaHCO3 H2SO4
Alanine insoluble insoluble B to R insoluble insoluble insoluble insoluble
Aniline insoluble soluble B to R insoluble insoluble insoluble soluble
Benzamide insoluble insoluble B to R insoluble soluble insoluble insoluble
Benzoic acid insoluble slightly same slightly insoluble insoluble insoluble
soluble soluble
Chlorobenzene insoluble insoluble same insoluble insoluble insoluble insoluble
Cyclohexane insoluble soluble same insoluble insoluble insoluble insoluble
Ethylacetate insoluble soluble same insoluble soluble soluble soluble
Hexane insoluble insoluble B to R insoluble soluble soluble insoluble
E-/α-napththol insoluble soluble same slightly insoluble insoluble slightly
soluble soluble
Dimethylamine insoluble insoluble same insoluble soluble soluble evolution
of gas
Phenol slightly soluble B to R insoluble insoluble insoluble insoluble
soluble
Salicylic acid slightly slightly B to R slightly soluble insoluble soluble
soluble soluble soluble
Sulfanilic acid slightly insoluble B to R slightly slightly insoluble insoluble
soluble soluble soluble

Figure 2: 3:
Figure Solubility of of
Solubility Alanine
Aniline

Figure 1: Diagram of Solubility Classification

 Figure 4: Solubility of Benzamide Figure 5: Solubility of Benzoic Acid

Figure 7: Solubility of Cyclohexane Figure 6: Solubility of Chlorobenzene

IV.
Answers to Guide Questions:

1. Give the rationale behind the solubility of the compounds in each solubility class.
a) Water-soluble Acid (SA)
Compounds in this group are partially polar so they are soluble in both water and ether. They are
good proton donors and they turn blue litmus to red.

b) Water-soluble Base (SB)

 Compounds in this group are partially polar so they are soluble in both water and ether. They are
good electron pair donors and they turn red litmus to blue.

c) Water-soluble Neutral (SN)

Compounds in this group are partially polar so they are soluble in both water and ether. The
litmus is unchanged.

d) Ether-insoluble (S2)
Compounds in this group are very polar which makes them soluble in water but insoluble in ether.

e) Strong Acidic Compounds (AS)

Compounds in this group can easily donate protons. They are predominantly nonpolar so they
are insoluble in water. They are soluble in 5% NaOH and 5% NaHCO 3 which produces water-soluble
salts.

f) Weak Acidic Compounds (AW)

Compounds in this group are more resistant proton donors. They are predominantly nonpolar so
they are insoluble in water. They are soluble in 5% NaOH which produces water-soluble salts, but, they
are insoluble in 5% NaHCO3 because it is not acidic enough to react with it.

g) Basic Compounds (B)

Compounds in this group are good electron pair donors. They form hydroxide anions in aqueous
solution and they react with acid to form salts.

h) Miscellaneous Neutral Compounds (NM)

Compounds in this group contain sulfur or nitrogen and they undergo hydrolysis and reduction
when subjected to heat.

i) Neutral Compounds (N)

Compounds in this group contain functional groups with oxygen but without sulfur or nitrogen.
They are unsaturated and are easily sulfonated.

j) Inert Compounds (I)

Compounds in this group do not undergo sulfonation.

2. Complete the diagram.

[Refer to diagram above]
Table 2: Solubility Classification
Class Sample Other Functional Groups Present
SA none monofunctional polar compounds
(up to about five carbons)
e.g. carboxylic acids
SB methylamine* monofunctional polar compounds
(up to about five carbons)
e.g. amines
SN ethylacetate monofunctional polar compounds
(up to about five carbons)
e.g. alcohol, aldehyde, ketone,
ester, amides, nitriles
S2 alanine polycarboxylic acids; amine salts;
metal salts of carboxylic acids;
ammonium salts; di- and
polyfunctional compounds
including sugars, amino acids,
polyhydric alcohols
AS benzoic acid carboxylic acids; sulfonic acids;
salicylic acid phenols substituted with
sulfanilic acid polyhalide nitro group and
aldehyde groups; phenols with
electron withdrawing groups in
ortho and/or para position/s
AW phenol phenols; enols; primary and
E-/α-naphthol secondary nitro compounds;
sulfonamides of primary amines
B aniline primary, secondary, tertiary
amines except di- and triaryl
amines, hydrazines, N,N-dialkyl-
carboxamides
NM benzamide nitriles; amides; sulfanomides of
secondary amines; aromatic nitro
compounds
N none neutral polar compounds (most
containing oxygen); alcohols,
aldehydes, anhydrides, esters,
ethers, ketones, unsaturated
hydrocarbons
I chlorobenzene alkyl and aryl halides; aromatic
 cyclohexane hydrocarbons; saturated
hexane hydrocarbons; diaryl ether

V. Conclusions and Recommendations

The solubility of compounds depends on different factors such as polarity, molecular weight,
molecular structure, intermolecular forces of attraction, acidity and basicity. Solvation is mainly governed
by the “like dissolves like” principle which means higher solubility between polar solutes and solvents and
nonpolar solutes and solvents.

It is recommended that the students be extra careful in handling the reagents so as to avoid
contamination because this may lead to different or erroneous results.

VI. References:

 The Essentials of Organic Chemistry, 2nd Edition by Paula Yurkanis Bruice

 Exploring Life through Science: Chemistry by Aristea Bayquen

 Chemistry: the Central Science, 9th Edition by Theodore Brown

 Chemistry by Estrella Mendoza

 Organic Experiments, 3rd Edition by Louis Feiser

 Modern Experimental Organic Chemistry, 4th Edition by Royston Roberts

VII. Contributions of Members

1) Albarico
-Introduction to Discussion
-Typing and Printing
2) Bojare
-Diagram
-Pictures of Results
3) Hernendez
-Answers to Guide Questions
-Conclusion and Recommendations