Experiment 1: Solubility Behavior of Organic Compounds

Answers to Questions:
1. State what types of intermolecular forces are present in solutions formed due to intermolecular
attractions between the solute and the solvent.
Three compounds, ethyl alcohol, acetone and sucrose were dissolved in water. This implies that the strong
dipoles of water were able to break the strong electrostatic attractions between the ions of these
compounds. This shows that the dissolving of ethanol, acetone and sucrose in water is generally because
of the formation of London dispersion, dipole-dipole and H-bonding. In addition, only ethyl alcohol and
acetone were able to dissolve in water. This indicates the non-polarity of ethyl alcohol and acetone since
ether is a non-polar solvent. Ether was able to dissolve ethanol and acetone through London forces.
2. Write the balance chemical equations for solute-solvent combinations that are formed due to chemical
reactions.
Benzoic acid NaOH :C6H5COOH(s) + OH-(aq) C6H5COO-(aq) + H2O(l)
Benzoic acid - NaHCO3: C6H5COOH(s) + HCO3-(aq) C6H5COO-(aq) + H2CO3(aq)
Phenol NaOH: C6H5OH(aq) + OH-(aq) C6H5O-(aq) + H2O(l)
Aniline HCl: C6H5NH2(aq) + H+(aq) C6H5NH3+(aq)
Benzyl Alcohol - H2SO4: C6H5CH2OH(aq) + 2H2SO4(aq) C6H5CH2OSO3H(s) + HSO4-(aw) + H3O+(aq)
Benzaldehyde - H2SO4: C6H5COH(aq) + 2H2SO4(aq) C6H5COSO3H(S) + HSO4-(aq) + H3O+(aq)
3. On the basis of solubility behavior, show how each of the following pairs of compounds may be
distinguished from each other.
a. CH3NH2 and CH3(CH2)5CH2NH2
Test Compound

Water

Soluble: CH3NH2

Insoluble:
CH3(CH2)5CH2NH2

Since CH3(CH2)5CH2NH2 has a longer hydrocarbon chain making it more non-polar, its water solubility
is less than CH3NH2.

b. CH3CHO and HOCH2CHO

Test Compound
Ether
Insoluble: HOCH2CHO
Soluble: CH3CHO

Since CH3CHO is slightly non-polar it can dissolve in ether more than HOCH 2CHO.
c. Benzylamine and Benzyl alcohol
Test Compound
5% HCl
Insoluble: Benzyl alcohol
Soluble: Benzylamine

Since Benzylamine contains an amine group it is a basic organic compound thus, it will dissolve in 5%
HCl.

References:
Organic Chemistry Laboratory Manual. Institute of Chemistry, UP Diliman. 2008.
http://www.elmhurst.edu/~chm/vchembook/170solutions.html
Fuson R. and R. Shriner. 1981. The Systematic Identification of Organic Compounds. John Wiley and
Sons, Inc., New York.