LAB 6 COMPARATIVE INVESTIGATION OF

ORGANIC COMPOUNDS
PRE-LAB
1. Differentiate the following types of functional
groups
a. Principal groups play a key role in the
determination of structure and reactivity.
Subordinate groups come into play once the
confirmation for principal groups has been
reached.
2. Enumerate the different interactive forces
involved during a solution process
Hydrogen Bonding - is the electrostatic
attraction between polar molecules that
occurs when a hydrogen (H) atom bound to a
highly electronegative atom such as nitrogen
(N), oxygen (O) or fluorine (F) experiences
attraction to some other nearby highly
electronegative atom.
Dipole-Dipole - Dipole-Dipole interactions
result when two dipolar molecules interact
with each other through space. When this
occurs, the partially negative portion of one of
the polar molecules is attracted to the partially
positive portion of the second polar molecule.
This type of interaction between molecules
accounts for many physically and biologically
significant phenomena such as the elevated
boiling point of water.
London Dispersion Forces - (LDF, also known as
dispersion
forces,
London
forces,
instantaneous dipoleinduced dipole forces,
or loosely van der Waals forces) are a type of
force acting between atoms and molecules.
They are part of the van der Waals forces.
Vander Waals Forces - is the sum of the
attractive or repulsive forces between
molecules (or between parts of the same
molecule) other than those due to covalent
bonds, or the electrostatic interaction of ions
with one another, with neutral molecules, or
with charged molecules.[1] The resulting van
der Waals forces can be attractive or repulsive
A. Observation of Physical State at Room
Temperature, Color and Odor of Samples
Table 1. Intrinsic properties of samples

As shown in the table, most of the hydrocarbons are

clear. The result of the experiment showed that
Phenol becomes red upon oxidation and white
crystals for benzoic acid. The odors of the
compounds are quite similar to each other but still
have different identity. Cyclohexane and DCM both
have paste-like odor. Ethanol smells like alcohol
while benzoic acid is odorless. Ethyl acetate has
plastic balloon odor while ethylamine has urine odor
or can be ammoniacal odor because of its
functional group, amine.
B. Test for Solubility Properties of Sample in H2O,
5% NaOH solution and 5% HCl solution
Table 2. Solubility of sample in different solvents

The solubility properties of organic compounds using

H2O, 5% NaOH solution and 5% HCL solution indicates
whether the solid sample is soluble or insoluble and if
the liquid sample is miscible and immiscible. Solubility
of sample to the solvent is related to polarity of the
two substances and the intermolecular forces of
attraction during the solution process. The like
dissolves like principle is involved. Water is a polar
solvent so the sample that is soluble or miscible with
water is also polar. Based on the results, ethanol,
phenol, ethyl acetate and ethylamine are polar
compounds. The solubility in 5% NaOH solution of a
water insoluble sample is an indication that acidic
functional group is present. Compounds that behave
as bases in aqueous solution are detected by their
solubility in 5% HCl solution.
Ethanol and phenol are miscible while benzoic acid is
very soluble in 5% NaOH solution. The rest of samples
are immiscible. Ethanol and ethylamine are miscible
in 5% HCl solution while the rest of the samples are
immiscible and benzoic acid is insoluble.
Reaction with litmus paper indicated acidity, basicity
or neutrality of water-soluble samples. Acidic solution
turns blue litmus paper to red and red litmus paper to
red. Blue litmus paper to blue and red litmus paper to
blue indicates a basic solution. Neutral solution is
characterized by blue to blue litmus paper and red to
red litmus paper.

2C2H2 + 5O2 4CO2 + 2H2O + heat

Based on the table, cyclohexane, phenol,
ethyl acetate and ethylamine are flammable
with luminous flame while ethanol with nonluminous flame. DCM and benzoic acid are
both non-flammable
LAB
7

CLASSIFICATION
HYDROCARBONS

As shown in the table, phenol and ethyl

acetate are acidic while ethylamine is basic.
Ethanol is a neutral sample. Cyclohexane,
DCM and benzoic acid were not subjected to
the litmus paper test because of their
immiscible property with water.

The result of the Ignition test indicates the

presence of unsaturated or high carbon to
hydrogen ratio. The degree of luminosity can
be assessed by the presence of yellow or
luminous flame. The aromatic compounds
burn with sooty flame due to the incomplete
combustion, which causes the formation of an
unburned carbon. The higher the number of
Carbon atoms, the higher the degree of
luminosity. In addition, the higher the Carbon:
Hydrogen Ratio, the higher the degree of
luminosity. In terms of degree of luminosity:
aromatic compound > unsaturated
hydrocarbon > saturated hydrocarbon.
Complete combustion is indicated by a blue
flame (non-luminous) and there is more heat
than light, the carbon is completely oxidized.
2C10H22 +31O2 20CO2 +22H2O
Incomplete combustion is indicated by a
yellow flame (luminous) and there is much light
than heat; the carbon is not completely
oxidized.

TESTS

FOR

Hexane alkane hydrocarbon with a chemical

formula of C6H14, has a molar mass of 86.18 g/mol,
and a boiling point of 69C. Isomers of hexane are
mostly non-reactive, and are frequently used as
solvents in organic reactions because they are very
non-polar. It is a very important constituent in
gasoline and is also used in food processing.

1. Differentiate:
a. Acyclic and cyclic
Cyclic hydrocarbons are molecules that have
carbon atoms that are combined to form one or
more rings. Acyclic hydrocarbons are carbons
that are combined to form straight or branched
chains.
Cyclic Hydrocarbons are those whose molecules
have carbon atoms that are combined to form
one or more rings or various other structures.
Aliphatic (non-cyclic or Acyclic) Hydrocarbons
are those whose molecules have carbon atoms
that are combined to form straight or branched
chains. Aliphatic compounds burn readily and are
toxic.
b. Saturated,
unsaturated,
unsaturated

and

actively

A Saturated compound contain only one carboncarbon signle bond. all the four bonds of carbon
are fully utilised and no more hydrogen or other
atoms can attach to it. Thus, they can undergo
only substitution reactions. (aka ALKANES)
An Unsaturated Compound contain one double
covalent bond between carbon atoms or a triple
covalent bond between carbon atoms. the bonds
of carbon are not fully utilised by hydrogen atoms,
more of these can be attached to them. Thus,
they undergo addition reactions as they have two
or more hydrogen atoms less than the saturated
hydrocarbons.
c. Aliphatic and aromatic

Aliphatic compounds in organic chemistry

are the non aromatic compounds. They can be
either cyclic or acyclic. Alkanes, alkenes, alkynes
and their derivatives are mainly considered as
aliphatic compounds. These can have branched
or linear structures and can be either saturate
(alkanes) or unsaturated (alkenes and alkynes).

An aromatic compound contains a set of

covalently-bound
atoms
with
specific
characteristics: A delocalized conjugated
system, most commonly an arrangement of
alternating single and double bonds. Coplanar
structure, with all the contributing atoms in the
same plane. Contributing atoms arranged in one
or more rings
2. Give the rxn and general mechanism of:
a. Baeyers Test
b. Bromine Test (review org notes)
c. Nitration (review org notes)
d.
The physical characteristics of each sample were
noted. All the organic compounds use dare clear,
colorless liquid. Each compound has their own
characteristic
odor
that
makes
them
distinguishable from the others. The solubility or

miscibility of the compounds in H2SO4 indicates

whether the sample is a very weak base (can be
protonated) or a neutral compound (cannot be
protonated).The dissolution of compounds in
H2SO4 may also produce large amounts of heat
and/or a change in the color of the solution,
precipitation or any combination of these.
* H2SO4
-soluble (very weak base)Esters, Ketones, Alkenes,
Aldehydes Alcohols
- insoluble (neutral compound)Alkanes, Aryl
halides, Alkyl halides, most aromatic hydrocarbons
The ignition test was performed to indicate the
presence of unsaturation or high carbon to
hydrogen ratio. Generally, high carbon to
hydrogen ratio equals high luminosity and the
more the flame produces black smoke or soot.
The degree of luminosity can be assessed by the
presence of yellow flame and soot. Aromatic
compounds burn with sooty flame due to the
incomplete combustion which causes the
formation of an unburned carbon. Aromatic
compound
is
greater
than
unsaturated
hydrocarbon, and unsaturated hydrocarbon is
greater than saturated hydrocarbon in terms
of degree of luminosity. Complete combustion is
indicated by a blue flame (non-luminous) and
there is more heat than light; hence the carbon is
completely oxidized. On the other hand,
incomplete combustion is indicated by a yellow
flame(luminous) and there is much light than heat;
hence the carbon is not completely oxidized.

Complete Combustion
CxHY + O2 CO2 + H2O
Incomplete Combustion
CxHY + O2 CO2 + H2O + C(soot) + CO

The test for Active Unsaturation was accomplished

in two ways: Baeyers test and Bromine test. Both
determine the presence of double bond in each
organic compound. In the Baeyers test, the
reagent used was 2%KMnO4 solution. The positive
result that must be obtained in the test is the
decolorization of a purple solution followed by
formation of a brown precipitate. All but
cyclohexene gave a negative result to the test. It
indicates that cyclohexene is positive for the
active unsaturation test and that it contains
double bond in its chemical structure. In the
reaction, Mn7+ is reduced to Mn4+which means
that alkene is oxidized to a diol in the process
of redox
reaction.
Alkenes
react
with
potassiumpermanganate (KMnO4) to give a diol
and MnO2. Aromatic compounds do not react in
this test because of their stability.
Cyclohexene + KMnO4(purple) 1,2 cyclohexanediol (colorless)
+ KMnO2(brown)

The reagent used in Bromine test was 0.5% Br2 in CCl4.

A positive result is obtained by decolorization of an
orange solution. In this case, cyclohexene decolorized
immediately and became a clear solution while the
other compounds still needed exposure to UV lighting
order to decolorize. From there, the test readily gave a
positive result to cyclohexane which makes it actively
unsaturated in the two different tests performed. The
alkenes react with Br2 to form a trans-dibromoalkane.
The reaction involves electrophilic addition. Aromatic
compounds do not react because of their stability;
however, they will react slowly upon using FeBr3 or
through the action of UV light.
The test for Aromaticity was performed through
Nitration. The reagents used were HNO3 and H2SO4.
A positive result in the testis obtained when a yellow
oily layer is formed. Benzene and toluene gave a
positive result and therefore the two compounds are
considered aromatic. Other than that, the two
compounds are also cyclic and planar in their chemical
structure and they obey Huckels rule that is why they
are considered aromatic compounds. The H2SO4 acts
as a catalyst and facilitates the formation of nitronium
ion (NO2+), an electrophile. One hydrogen in the
benzene ring is substituted by the nitronium ion that is
why the reaction involves electrophilic substitution
HNO3 + H2SO4 NO2+ + 2H2SO4- + H3O+
Benzene + NO2+ nitrobenzene

The last test performed was Basic Oxidation,a test for

alkylated aromatics or arenes. The reagents used were
2% KMnO4 and 10%NaOH. A positive result in the test
will produce a violet solution (MnO4) or brown
precipitate (MnO2). NaOH provides a basic
environment. The alkyl group of the aromatic
compound is oxidized to a carboxylic acid, therefore
involves a redox reaction. Mn7+is reduced to Mn6+/4+
depending on the extent of the reaction.

Methylbenzene + KMnO4 benzoic acid + MnO4

LAB 8 CLASSIFICATION TESTS FOR ORGANIC

HALIDES
1. Differentiate:

Primary carbon atom - bonded to one

carbon atom
Secondary carbon atom - bonded to two
carbon atoms
Tertiary carbon atom - bonded to three
carbon atoms
Quaternary carbon atom - bonded to four
carbon atoms

other
other
other
other