Name: Lim, Angella Rainbow Date Performed: April 15, 2010

Lab Partner: Kevin Villavicencio

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.
SOLUTE SOLVENT 1 SOLVENT 2
Acetone with water:
dipole-dipole
with ether:
Dipole-dipole
Ethanol with water:
H-bonding
with ether:
Dipole-dipole
Sucrose with water:
H-bonding


2. Write the balanced chemical equations for solute-solvent combinations that are formed due to chemical
reactions.
SOLUTE SOLVENT 1 SOLVENT 2
benzyl alcohol with H2SO4 :
C6H5CH2OH + H2SO4 C6H5COOH +
2H2O + SO

aniline with HCl:
C6H5NH2 + HCl C6H5NH3
+
+ Cl
-


phenol with NaOH:
PhOH + OH
-
PhO
-
+ H2O

benzoic acid with NaOH:
C6H5COOH + OH
-
H2O +
C6H5COO
-

with NaHCO3 :
C6H5COOH + HCO3
-
H2O + CO2 +
C6H5COO
-

benzaldehyde with H2SO4 :
C6H5CHO + H2SO4 H2O +
CH3CH2CH=CH


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
Both are polar due to the presence of N atom but CH3(CH2)5CH2NH2 has a longer chain, which
implies that it is less polar. Water is a polar solvent; hence, CH3NH2 would be soluble because it only
has 1 carbon atom compared to the 7 atoms in CH3(CH2)5CH2NH2.
b. CH3CHO and HOCH2CHO
Acetaldehyde is soluble in water because of dipole-dipole interaction while h-bonding between water
and acetic acid exists. Ether will not dissolve HOCH2CHO because of the presence of ions and
therefore distinguish the two.
c. Benzylamine and benzyl alcohol
Name: Lim, Angella Rainbow Date Performed: April 15, 2010
Lab Partner: Kevin Villavicencio

Benzylamine has an amine group, which is very basic while benzyl alcohol has alcohol. Observing
their solubility in 5% HCl, we will see that benzylamine will dissolve in the acidic solvent. Benzyl
alcohol is only slightly basic so it wont be as soluble.

REFERENCES:
[1] Carbohydrates-Sucrose. 15 April 2010.
<http://www.elmhurst.edu/~chm/vchembook/546sucrose.html>.
[2] Bailey, Philip S., and Christina A. Bailey. Organic Chemistry: A Brief Survey of Concepts and Applications. Upper
Saddle River, N.J.: Prentice Hall, 2000.