Experiment 1 Solubility of Organic Compounds

Theoretical Data 1

Theoretical Data 2

Test compound

Hexane
Aniline
Benzamide
Cellulose
dichloromethane
benzyl alcohol
ethyl alcohol
ethyl acetate
Acetone
Sucrose
Toluene
Glycine
benzaldehyde
benzoic acid

Classification:

Water

Ether

+
+
+
+
+
+
+
-

5%
NaOH

Solvents
5%
NaHCO3

5% HCl

Conc.
H2SO4

+
+

+
+

+
+
+
-

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

For Water-Soluble Compounds:

Acetone Water: Hydrogen bonding and van der Waals forces
Acetone Diethyl Ether: Dipole (induced) dipole and van der Waals forces
Sucrose Water: Hydrogen bonding and van der Waals forces
Ethyl alcohol Water: Hydrogen bonding and van der Waals forces
Ethyl alcohol Dietheyl Ether: Dipole (induced) dipole and van der Waals
forces For Acidic Compounds:
Benzoic Acid NaOH: Ion (induced) dipole and van der Waals forces
Benzoic Acid NaHCO3: Ion (induced) dipole and van der Waals forces
Phenol NaOH: Hydrogen Bonding, Ion dipole, and van der Waals forces
For Basic Compound(s):
Aniline HCl: Ion dipole and van der Waals forces
For Neutral Compounds:
Benzyl alcohol H2SO4: Hydrogen bonding and van der Waals forces
Benzaldehyde H2SO4: Ion (induced) dipole and van der Waals forces

Solutions with water:

ethanol and water: H-bonding
sucrose with water: H-bonding
phenylmethanol with water: H-bonding (partial solubility)
Solutions with ether:
sucrose with ether: London dispersion
phenylmethanol with ether: London dispersion

2. Write the balanced chemical equations for solute-solvent combinations that

are formed due to chemical reactions.

benzoic acid: C6H5COOH + NaOH

benzamide: C6H5CONH2 + H2SO4
phenylmethanal: C6H5CHO + H2SO4
phenol:
C6H5OH + NaOH
aniline:
C6H5NH2 + HCl
A2.
For Acidic Compounds:

-> C6H5COO- Na+ + H2O

-> C6H5COSH2 + HNO2
-> C6H5
-> C6H5O- Na+ + H2O
-> C6H5NH3 + Cl-

Benzoic Acid NaOH

C_6 H_5 COOH+NaOH H_2 O+ C_6 H_5 COO^-+Na^+
Benzoic Acid NaHCO3
C_6 H_5 COOH+NaHCO_3 H_2 O+ CO_2+C_6 H_5 COO^-+Na^+
Phenol NaOH
PhOH+NaOHH_2 O+ PhO^-+Na^+

3. On the basis of solubility behaviour, show how each of the following pairs of
compounds may be distinguished from each other:
a. CH3COOH and CH3(CH2)5COOH - Diethyl ether
b. CH3CH2OCH2CH3 and CH3CH2OH NaOH
c. toluene and benzaldehyde - concentrated H2SO4
d. tert-butyl chloride and tert-butanol - H2O
Reference: http://webapps.utsc.utoronto.ca/chemistryonline/solubility.php