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Chem 31.1
Elementary Organic Chemistry Laboratory

Solubility of Organic Compounds

Asparin, Jade Frances B.
College of Science, University of the Philippines-Cebu, Philippines
Contact number: +639954619301Email address: jbasparin@up.edu.ph

RESULTS AND DISCUSSIONS

1. State what types of intermolecular forces are present in the solutions formed due to
intermolecular attractions between solute and solvent.

a) Dipole-dipole interactions
Dipole-dipole interaction occurs whenever two polar molecules align themselves with each
other so that the positive end of one dipole is near the negative end of another and vice versa. Dipole
simply means a bond with two poles; similar to a magnet. A molecule is considered to contain polar
bonds if the electronegativity difference is between 0.4 and 1.7. Since many molecules are polar, this
is a common intermolecular force (Chemlibretexts.org, 2018). For that reason, many compounds
used in the lab experiment exhibited a dipole-dipole interaction.
b) London dispersion forces
This type of intermolecular force, in contrast with dipole-dipole, is a force between two
nonpolar molecules. The electrons of one molecule are attracted to the nucleus of the other molecule
while repelled by other molecule’s electrons causing short-lived instantaneous dipole moments
(Chemlibretexts.org, 2018). This is the weakest among all types.
c) Hydrogen bonding
This is a special kind of dipole-dipole interaction. It results from the attractive force between
a hydrogen atom bonded to either an oxygen, nitrogen, or fluorine atom. The partially positive end of
hydrogen is attracted to the partially negative end of the oxygen, nitrogen, or fluorine of another
molecule. Hydrogen bond strengths range from 4 kJ to 50 kJ per mole of hydrogen bonds.

2. Write the balanced chemical equations for solute-solvent combinations that are formed due to
chemical reactions

 Aniline with:
o H2O: C6H5NH2(aq) + 2H2O(l) → C6H5NH4+(aq) + 2OH- (aq)
 o HCl: HCl(aq) + C6H5NH2 → C6H7NH+Cl-
 Benzaldehyde with:
o H2SO4: C7H6O + H2SO4 → C7H8O5S
 Benzoic acid with:
o NaOH:C6H5COOH(s) + NaOH(aq) → C6H5COO- Na+(aq) +H2O(l)
o NaHCO3: C6H5COOH + NaHCO3 → C6H5COO- + Na+ + H2O + CO2
 Butanoic acid with:
o H2O: HC4H7O2(aq) + H2O(l) → H3O+(aq) + C4H7O2-(aq)
 Ethyl benzoate with:
o NaOH: C9H10O2 + NaOH(aq) → C7H5NaO2 + C2H5OH
o H2SO4: C9H10O2 + H2SO4 → C9H10O + H2O + SO4
 Stearic acid with:
o H2SO4: C18H36O2 + 4H2SO4 → C18H44O18S4
 Sucrose with:
o H2O: C12H22O11(aq) + H2O(l) → 2C6H12O6(aq)
 Thymol with:
o NaOH: C10H14O + NaOH → C10H13ONa + H2O
 Urea with:
o H2O: CO(NH2)2 + H2O → 2NH3 + CO2

3. Based on solubility behaviour, show how each of the following pairs of compounds may be
distinguished from each other using a single test. Justify your answers

a. methylamine and heptylamine – water solubility test

o This test is helpful in differentiating the two compounds since methylamine dissolves
more readily in water in comparison to heptylamine. The reason for this is that the
solubility falls off as the hydrocarbon chains get longer, more so after about six
carbons. In this state, the hydrocarbon chains have to force their way between water
molecules to break the hydrogen bonds but it becomes impossible to replace them by
anything as strong and so the compound becomes poorly soluble in water as the
length of the carbon chain grows.
b. acetaldehyde and acetic acid - NaHCO3 test
o Sodium bicarbonate will react with acetic acid to produce aqueous sodium acetate and
carbonic acid. However, aldehydes such as acetaldehyde are not acidic thus it will not
react with sodium bicarbonate.
c. benzylamine and benzyl alcohol – HCl solubility test
o Benzylamine will react with aqueous HCl to form a water-soluble salt. On the other
hand, benzyl alcohol will not react with the solution. The alcohol is also insoluble
when placed together with the acid.
d. octanoic acid and phenol – NaHCO3 test
o Strongly acidic compounds such as carboxylic acids react with NaHCO3 to form
water-soluble salts. The reaction also produces bubbles of carbon dioxide (CO2).
Phenols are less acidic than carboxylic acids and do not react with NaHCO3 to form
water-soluble salts.
e. heptane and hept-2-ene – H2SO4 test
o This test can be used to distinguish between the two since compounds such as alkenes
react with sulfuric acid in the cold to produce alkyl hydrogen sulfates. Alkanes, on the
 other hand, will not. This is because alkanes are stable compounds and are generally
unreactive. Only in oxidation reaction are alkanes mostly applied.

4. Why is it important to perform the solubility tests in the corrected order in Fig 1?

It is important to perform the solubility tests in correct order because it would help us lead to
appropriate conclusions regarding the presence or absence of certain functional groups and the nature
of the compound by following a series of steps. A flowchart provides us with multiple possible
outcomes that direct us to the next pair of choices until it arrives from the general to the more
specific identification of the compound.

5. Why is it unnecessary to test the pH (via litmus paper) for remaining compounds that are
already insoluble in water?

Since many polar organic compounds are soluble in water such as alcohols, aldehydes,
ketones, amines, carboxylic acids, and a few phenols; it is important that the pH of water-soluble
compounds are tested to see if they areacidic or basic. A pH of 4 or lower indicates a carboxylic acid.
A pH of 8 or higher indicates an amine.

6. Why is it unnecessary to test miscellaneous neutral compounds that dissolve in HCl and
contain N or S further with H2SO4?

Many compounds that are neutral toward 5% hydrochloric acid solution behave as bases in
more acidic solvents which is why it is unnecessary to test miscellaneous neutral compounds further
with H2SO4 because compounds containing sulfur or nitrogen have an atom with an unshared pair of
electrons thus it would be expected that they will dissolve in a strong acid such as the concentrated
sulfuric acid. Testing the compounds would just be redundant since we already know their behaviour
in acidic solvents.

7. In other solubility charts, an additional test for solubility in ether (diethyl ether) may be
performed for water-soluble compounds. Low-MW polar compounds (SA, SB, S1)will dissolve
in ether. However, organic salts, such as RCOO─Na+and aminehydrochlorides, and
compounds with more than 1 polar functional groups (dicarboxylicacids, amino acids, diols,
etc.) will not dissolve in ether, comprising another solubilityclass, S2. Rationalize these results.
Which of the test compounds would belong to S2?

Two test compounds are found to be immiscible with ether and is part of the solubility class,
S2 which are sucrose and urea since it differs from water such that it cannot dissolve ionic
compounds. Moreover, ether also dissolves most water insoluble compounds; therefore in the
identification of solubility class, the importance of ether is for water soluble compounds only.
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