SOLUBILITY OF ORGANIC COMPOUNDS

J.V. DE GUZMAN
DEPARTMENT OF CHEMICAL ENGINEERING, COLLEGE OF ENGINEERING
UNIVERSITY OF THE PHILIPPINES, DILIMAN QUEZON CITY, PHILIPPINES
DATE PERFORMED: JANUARY 28, 2015
INSTRUCTORS NAME: ALLAN KENNETH REGUNTON

ANSWERS TO QUESTIONS
1. What are the intermolecular forces of attraction involved between
the solutes dissolved in their solvents?
From the results of the experiment, compounds that are soluble with
water are ethanol, sucrose and acetone. The following are the
intermolecular forces of attraction involved in the dissolution of the given
solutes:
Ethanol London dispersion forces, dipole-dipole (Hydrogen
bonding)
The partially negative H in the hydroxyl group of ethanol attracts the
partially negative oxygen containing a lone pair on water thus forming a
special dipole-dipole interaction which is hydrogen bonding. On the hand,
London dispersion force is an intermolecular force always present between
two molecules and thus present in the dissolution of ethanol in water.

Sucrose London dispersion forces, dipole-dipole (Hydrogenbonding)

Sucrose contains seven hydroxyl groups in its structure and thus it
also forms a strong special dipole-dipole interaction (H-bonding) with water
molecules. The weak dispersion forces, which is always present between
molecules, is also an intermolecular force of attraction present in the
dissolution.
Acetone London dispersion forces, dipole-dipole (H-bonding)
Acetone belongs in the ketone functional group (R-O-R). Its partially
negative oxygen with a lone pair attracts the partially negative H in water
thus forming strong hydrogen bonds. London dispersion force is also present
in the interaction of these two molecules.

When diethyl ether is added to these test compounds, acetone and

sucrose are those that dissolved in the solvent since they are less polar
compared to the insoluble ethanol. The following are the intermolecular
forces of attraction present:
Acetone dipole-dipole, London dispersion forces
Acetone is polar because of its oxygen containing a lone pair and its
the same with diethyl ether. Thus, the two are soluble with each other
because of the dipole-dipole interaction and dispersion forces which is
present always between two molecules.
Sucrose dipole-dipole, London dispersion forces
2. What are balanced chemical equations for solutes that are
dissolved because of the reaction with the solvent?
Compounds that are insoluble in water but dissolved in 5% NaOH
solution are benzoic acid and phenol since these compounds are acids and
the dissolution that occurs is an acid- base neutralization reaction given
below:
a. NaOH + benzoic acid
C6H5COOH(s) + OH-(aq) C6H5COO-(aq) + H2O(l)

b. NaOH + phenol
C6H5OH(aq) + OH-(aq) C6H5O-(aq) + H2O(l)

On the other hand, these two compounds were tested for solubility
with NaHCO3, a weak base. Benzoic acid dissolved in NaHCO 3 implying its a
stronger base compared to phenol.
c. NaHCO3 + benzoic acid
C6H5COOH(s) + HCO3-(aq) C6H5COO-(aq) +H2CO3(aq)

The test compound that showed positive result with HCl is aniline
which is a base. This dissolution is also brought about by acid-base
neutralization reaction:
HCl + Aniline
d.

H+(aq) + C6H5NH2(aq) C6H5NH3+(aq)

Under solubility test with concentrated sulfuric acid, benzyl alcohol

and benzaldehyde were found to be neutral compounds that can be easily
protonated since they showed positive test results with H2SO4.
Benzaldehyde + H2SO4
e.
H2SO4(aq) + C6H5COH C6H5COH3 + SO4-2

f.

Benzyl alcohol + H2SO4

H2SO4(aq) + C6H5CH2OH C6H5CH2OH2+ + HSO4-

3. On the basis of solubility behavior, determine the best solvent to

differentiate the following the pairs of compounds.
a. CH3COOH and CH3(CH2)5COOH- water
b. CH3CH2OCH2CH3 and CH3CH2OH- water
Toluene and benzaldehyde- concentrated H2SO4
c.
d. tert-butyl chloride and tert-butanol- water
References:
Kelly, W. Organic Qualitative Analysis Solubility Test. Southwestern Oklahoma
State
University.
[Online].
2014.
http://faculty.swosu.edu/william.kelly/pdf/qo3.pdf (accessed January 28,
2015).
Silberberg, M. Chemistry: The Molecular Nature of Matter and Change 5 th ed.
Chapter 12: Intermolecular Forces: Liquids, Solids and Phase Changes.
McGraw-Hill Companies: New York, 2009. pp 451-456.
University of Delaware. Identifying an Unknown Compound by Solubility,
Functional
Group
and
Spectral
Analysis.
[Online].2014.http://www.udel.edu/chem/CHEM322/Handouts/unknowns_lab
_handout.pdf (accessed January 28, 2015)
Rowley, H.H. and Reed, W.R. Solubility of Water in Diethyl ether at 25. Journal of
American Chemical Society. 1951. 73, pg-2960.