Andre B. Flores Chem 31.

1
2013 44268 Sir Ser Perez

Experiment 1 Solubility of Organic Compounds

1.) For solutes that are dissolved because of intermolecular attractions with the solvent,
state the intermolecular forces of attraction involved.

Acetone + water: H-bonding, dipole-dipole, London dispersion forces
Acetone + diethyl ether: H-bonding, dipole-dipole, London dispersion forces
Ethyl alcohol + water: H-bonding, dipole-dipole, London dispersion forces
Ethyl alcohol + diethyl ether: dipole-dipole, London dispersion forces
Sucrose + water: dipole-dipole, London dispersion forces

2.) For solutes that are dissolved because of reaction with the solvent, write the
balanced equation involved:

Benzoic acid + NaOH:
C
6
H
5
COOH + NaOH(aq) -> C
6
H
5
COO- Na+(aq) + H
2
O(l)

Benzoic acid + NaHCO3:
C
6
H
5
COOH + NaHCO3(aq) -> C
6
H
5
COO-(aq) + Na+(aq) + H
2
O(l) + CO
2
(g)

Phenol + NaOH:
PhOH + NaOH -> PhONa + H
2
O

Aniline + HCl:
Aniline + H
3
O
+
-> AnilineH(+) + H
2
O

3. On the basis of solubility behavior, determine the best solvent to differentiate the
following pairs of compounds:

a. CH
3
COOH and CH
3
(CH
2
)
5
COOH NaHCO
3

b. CH
3
CH
2
OCH
2
CH
3
and CH
3
CH
2
OH Dimethyl sulfoxide or water

c. toluene and benzaldehyde - H
2
SO
4


d. tert-butyl chloride and tert-butanol - Water