ROCAFORT, Andrea Nicole Z.

2013-14862
Experiment 1
Solubility of Organic Compounds
Results:
TEST COMPOUND
A
B
C
D
E
F
G
H
I
J
K
L

CHEMICAL NAME
Benzoic acid
Tert-butyl
chloride/Toluene/Hexane
Tert-butyl
chloride/Toluene/Hexane
Benzyl alcohol
Benzaldehyde
Acetone/Ethanol
Phenol
Aniline
Tert-butyl
chloride/Toluene/Hexane
Sucrose
Benzamide
Acetone/Ethanol

1. For solutes that are dissolved because of intermolecular attractions with the solvent,
state the intermolecular forces of attraction involved.
Sucrose- It is considered polar because of the hydrogen bonding between the
OH group and water.
Ethanol- It is soluble in water due to the OH group which allows hydrogen
bonding but insoluble to diethyl ether because of the London dispersion forces
present.
Acetone- The carboxyl group is partially positive, allowing interactions to occur.
Summary:
Acetone + water: H-bonding, dipole-dipole, London dispersion forces
Acetone + diethyl ether: London dispersion forces
Ethanol + water: H-bonding, dipole-dipole, London dispersion forces
Ethanol + diethyl ether: dipole-dipole, London dispersion forces
Sucrose + water: dipole-dipole, London dispersion forces, H-bonding

2.) For solutes that are dissolved because of reaction with the solvent, write the
balanced equation involved:
Benzoic acid + NaOH:
C6H5COOH(s) + OH-(aq) -> C6H5COO-(aq) + H2O(l)
Benzoic acid + NaHCO3:
C6H5COOH(s) + HCO3(aq) -> C6H5COO-(aq) + H2O(l) + CO2(g)
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) -> C6H5COSO3H(s) + HSO4-(aq) + H3O+(aq)
Benzaldehyde + H2SO4
C6H5COH(aq) + 2H2SO4(aq) -> C6H5COSO3(s) + HSO4-(aq) + H3O+(aq)
3. On the basis of solubility behavior, determine the best solvent to differentiate the
following pairs of compounds:
a. CH3COOH and CH3(CH2)5COOHNaHCO3
b. CH3CH2OCH2CH3 and CH3CH2OH Dimethyl sulfoxide or water
c. toluene and benzaldehyde - H2SO4
d. tert-butyl chloride and tert-butanol - Water