SOLUBILITY OF ORGANIC COMPOUNDS

Data and Results

Compound Observation Classification

H2O 5% NaOH 5% NaHCO3 HCL
1 soluble N/A N/A N/A Group A
2 insoluble soluble Insoluble N/A Group B2
3 insoluble insoluble insoluble Soluble Group C
4 insoluble soluble Insoluble N/A Group B1
5 insoluble insoluble insoluble Insoluble Group D

Guide Questions:

1. Obtain from your instructor the list of organic compounds tested in the experiment. Based on how
you classified compounds 1 to 5; give the possible identity of the organic compounds.

Compound # Name of Compound Classification Observation

1 Acetone
2 Phenol
3 Diphenylamine
4 Benzoic Acid
5 Hexane
Group A  It is soluble in water (H2O) which indicates
that Acetone contains less than 5 carbon
atoms, have lower pH level and lighter
organic compound.
Group B2  It is insoluble in water (H2O) but soluble in
5% Sodium Hydroxide (NaOH) because it
ionized strong and weak acids including
phenol. Lastly, it is insoluble in 5% Sodium
Hydrogen Carbonate (NaHCO3) because it is
less acidic. Only strong acids react in 5%
NaHCO3 .
Group C  It is water-soluble compound that is
insoluble in 5% NaOH and 5% NaHCO3 but
soluble in Hydrochloric Acid (HCl) is
identified as amines, an organic base
compound that forms water-soluble amine
salts when reacted to HCl.
Group B1  It is insoluble in water, yet it is soluble in 5%
Sodium Hydroxide Solution and in 5%
Sodium Hydrogen Carbonate solution
because these bases react to form the
water-soluble benzoate ion. It has more than
5 carbon atoms compairing to Phenol which
have less than carbon atom
Group D  It is insoluble to all the reagents used.
2. Write the structures of compounds 1 to 5. Explain how each compound dissolved in the specific
solvents used in the experiment. Whenever necessary, support your explanation with the chemical
equation.

Compound Chemical Structure Explanation Chemical Equation

1. Acetone  Acetone dissolves
(C3H6O) completely in water
which results into
homogeneous solution.
When acetone mixed
with water hydrogen
bonds formed.
2. Phenol  Phenol dissolves in 5%
(C6H5OH) NaOH but not in H2O
and 5% NaHCO3
because it is slightly
acidic. Mixing it with
NaOh will release a H+
that will form sodium
phenoxide.
3. Diphenylamine  It is soluble in
(C12H11N) Hydrochloric Acid (HCL)
but not in water (H2O)
which immediately
considered as amine. It
is a basic compound
which dissolves in acid
completely because
they form hydrochloric
salts that are soluble in
aqueous medium.
4. Benzoic Acid  It is soluble in 5% NaOH
(C7H6O2) but not in water (H2O)
and 5% Sodium
Hydrogen Carbonate
(NaHCO3) which makes
it a strong acid,
wherein Benzoic Acid is
the simplest aromatic
Carboxylic Acid.
5. Hexane  It is insoluble in all of
(C6H14) the reagent used
because it has a fairly
equal distribution of
charge that makes it a
non-polar compound.
3. What other solvents may be used to further narrow down the classification of organic compounds
based on solubility. Discuss each.

Other Solvents Explantion

1. Sulfuric acid (H2SO4)
2. Phenolphthalein (C20H14O4)
 Water-insoluble compounds that are insoluble
in 5% HCl are tested with concentrated sulfuric
acid (H2SO4). Virtually all organic compounds
containing alkene functional groups or oxygen
or nitrogen atoms are soluble in concentrated
H2SO4. These functional groups typically react
with H2SO4 to form new compounds.
 Phenolphthalein is a presumptive test that
reacts with the hem molecule present in
blood. A positive reaction gives a pink color.
While bloodstains normally appear red-brown
in color, the color of the substrate or the age
of a stain may affect the appearance or
visibility of the stain. Phenolphthalein tests
are typically conducted on suspected
bloodstains prior to collection. While a
positive phenolphthalein reaction is indicative
of blood, it is only a presumptive test and false
positives are possible. Additionally, the
reaction is not species specific. Positive
reactions are not limited to human blood.
Positive reaction with the phenolphthalein
test, indicates the presence of blood.

References:

https://www2.estrellamountain.edu/faculty/farabee/biobk/BioBookCHEM2.html

https://www.academia.edu/6416813/Solubility_Classification_Using_Water_5_NaOH_5_HCL_5_NAHCO
3_Ether_Concentrated_H2SO4_and_85_H3PO4

https://www.academia.edu/10879682/Preliminary_Tests_and_Solubility_Classification_of_Organic_Co
mpounds

https://dps.mn.gov/divisions/bca/bca-divisions/forensic-science/Pages/forensic-programs-crime-scene-
phenol.aspx

http://www1.udel.edu/chem/CHEM322/Handouts/unknowns_lab_handout.pdf