EXPERIMENT 8
CLASSIFICATION TESTS FOR ORGANIC HALIDES
Fleur Sofia Josef Dela Cruz, Fatima Beatrice Diaz, Nicole Gea Divinasflores, Ruby Lynne
Duran, Nica Michaela Dy, Elishea Jhaira Ebuen, Margaret Claire Epistola
Group 3 1APH
INTRODUCTION
Organic halides are organic compounds
containing a halogen atom bonded to a
carbon (C) atom. Fluorine (F), Chlorine
(Cl), Bromine (Br), and Iodine (I) are all
types of halogen atoms. Most organic
halides are synthetic. Organic halides are not
flammable. If the α-carbon atom is
tetragonal or sp3 hybridized in the
compound, the organic halide may be
classified as primary, secondary or tertiary,
depending on the degree of substitution of
the α-hydrogen atom by an R-group.
Reactivity of these types of organic halides
can be differentiated via a substitution
reaction with a nucleophile, depending on
which reactant molecule (nucleophile or
organic halide) is involved in the rate-
determining step. If the rate of the reaction
is dependent on the organic halide, the
reaction is unimolecular: SN1. On the other
hand, if the rate of reaction is dependent on
both the organic halide and the nucleophile,
the reaction is bimolecular: SN2.
For the compounds to be classified, it must
undergo some tests. The Beilstein test is a
simple qualitative chemical test for halides.
It was developed by Friedrich Konrad
Beilstein, a Russian Chemist and Founder of
the famous Handbuch der Organischen
Chemie (“Handbook of Organic
Organic Chemistry Laboratory
Chemistry”). To conduct the test, a small
loop with one end of the copper wire is
made. The loop must be heated directly in
the oxidizing zone of a non-luminous flame.
Continuous heating must be done until the
green color imparted to the flame
disappears. The loop will be cooled slightly
and be dipped into the solid or liquid sample
that was given. The loop is then heated with
the sample in a non-luminous flame: first in
the inner zone, then in outer zone, and near
the flame’s edge. The green flame indicates
the presence of Chlorine, blue-green flame
for Bromine and blue flame for Iodine.
To test for SN1 reactivity, the given samples
were reacted with Alcoholic AgNO3. In
addition to that, to test for SN2 reactivity,
the samples were reacted with NaI in
Acetone. The solutions of the reagents
should not be turbid when used. The
objectives for this experiment –
classification tests for organic halides, are to
differentiate primary, secondary, and tertiary
organic halides based on their SN reactivity,
and to also differentiate between SN1 and
SN2 as reactive mechanisms with the organic
halides.
METHODOLOGY
MATERIALS NEEDED
The experiment required test tubes, matches,
copper wires, a burner, 2% ethanolic
AgNO3, calibrated droppers, a test tube
holder and rack, 15% NaI anhydrous
acetone, and n-butyl chloride, sec-butyl
chloride, tert-butyl chloride and
chlorobenzene as sample compounds.
n-butyl chloride
sec-butyl chloride
OPTIONAL: While hot, dip the loop in
tert-butyl chloride
2. Cool the loop slightly and dip it
chlorobenzene
Figure 1. Organic Halide Samples
A. Belstein Test: Copper Halide Test
1. Make a small loop with one end
of the copper wire. Heat the loop
directly in the oxidizing reagent
in the oxidizing zone of a non-
luminous flame. Continue
heating until the green color
imparted to the flame disappears.
Figure 2. Zone of a non-
luminous flame
some copper oxide powder and
reheat until the oxide adheres to
the loop.
into the solid or liquid sample.
Heat the loop with the sample in
a non-luminous flame: first in the
inner zone, then in the outer zone
near the edge of the flame. A
green flame indicates the the
presence of chlorine, blue-green
flame for bromine, and blue
flame for iodine.

Figure 3. (In order) Blue-green
flame for bromine, green flame
indicates the the presence of
chlorine, and blue flame for
iodine
B. SN1 Reactivity: Reaction with
Alcoholic AgNO3
Note: The solution of the reagent should not
be turbid when used.
Add 5 drops of the sample to 20 drops of 2%
ethanolic AgNO3. Shake and record
the time in seconds or minutes for a
silver halide precipitate to form.
Describe the color of the precipitate.
Figure 4. Silver halide precipitate
C. SN2 Reactivity: Reaction with NaI
in Acetone
Note: The solution of the reagent should not
be turbid when used.
Use dry test tubes for this experiment. Add 5
drops of the sample to 2 drops of
15% NaI in anhydrous acetone. Mix
the contents and note the time (in
seconds or minutes) required for a
precipitate to form. Describe the
color of the precipitate.
Figure 5. SN reactions or mechanisms
RESULTS AND DISCUSSION
On the experiment, we conducted an
experiment that revolves around the
different kinds of classification test for
organic halides with certain variation of
results.
Beilstein test
n-butyl chloride Green flame
Sec-butyl chloride Green flame
Tert-butyl chloride Green flame
Chlorobenzene Green flame
In Beilstein test, the presence of halide was
observed in all samples were each of it
exhibit a green flame appearance. The Green
flame was observed during the experiment
Reaction with 15%
and it shows a positive result. This Blue - NaI in anhydrous
green color is an emission of light that acetone
indicates that there is a formation of copper
halide through vaporizing.
n-butyl chloride White ppt
(1 second)

Reaction with 2%
ethanolic AgNO3 Sec-butyl chloride White ppt
(1.5 seconds)
n-butyl chloride White precipitate
Slowest – 3 mins
20 seconds Tert-butyl chloride Black solution
White ppt
Sec-butyl chloride Cloudy solution (1 minute)
White precipitate
2 mins
Chlorobenzene No precipitate
Tert-butyl chloride White precipitate
Fastest - 18 secs

Chlorobenzene No precipitate

The results show a certain order. The fastest

Chlorobenzene is the only reagent that did
not have any reaction, therefore it has no
precipitate. It is a slower process wherein
tert-butyl chloride will take 18 seconds to
react, followed by sec-butyl chloride, and
the slowest is the n-butyl chloride.
The kinetic reaction occured and it was
reliant to alkyl halide. It has a faster rate of
SN1 reaction when the carbocation is more
stable and it needs a leaving group for it to
occur. It was utilized by a solvent that is
ought to be a protic, polar solvent that
balance the carbocation intermediate
through increasing of the reaction rate
(solvation), The substrate dissociate to a
carbocation in a slow rate-limiting step and
the nucleophile will have a rapid attack and
with this kind of process the SN1 reaction
occur.
reaction goes to n-butyl chloride, followed
by sec-butyl chloride, and the slowest which
is the only one that reached a minute mark is
the tert-butyl chloride. Chlorobenzene, on
the other hand, had no reaction therefore
there is no precipitate.
This explains that the kinetic reaction was
dependent on the alkyl halide and
nucleophile. It is resulted by the impact of
N1 reaction an N2 reaction ( steric impact)
responses. It favors essential and optional
substrates with the help of a strong
nucleophile what parallels basicity and the
solvent that be in use should be a polar,
aprotic solvent.
POST-LAB ASSIGNMENT
 1. Which organic halide/s studied
is/are:
a. Positive with Beilstein test?
All organic halides namely n-
butyl chloride, sec-butyl
chloride, tert-butyl chloride, and
chlorobenzene produced green or
blue-green flame for Beilstein
test indicating the presence of
halide.
b. Most SN1 reactive
Tert-butyl chloride was the most
SN1 reactive for it was the first to
form white precipitate because it
has the most stable carbocation
intermediate. This is then
followed by sec-butyl chloride
and n-butyl chloride,
consequently.
c. Most SN2 reactive
n-butyl chloride was the most
SN2 reactive for it was the first to
produce white precipitate
because of its nucleophilic
strength and steric effect. This is
then followed by sec-butyl
chloride and tert-butyl chloride,
consequently.
d. Unreactive towards SN1 and
SN2?
Chlorobenzene is both unreactive
towards SN1 and SN2.
2. Which among the organic halides are
not reactive towards SN1 and SN2?
Explain your answer.
Chlorobenzene is unreactive towards SN1
and SN2 because:
SN1
Alkyl halide was the basis of kinetics for
SN1 reaction, making the stability of the
carbocation intermediate necessary for a
faster rate of reaction. Reaction requires a
good leaving group, with polar, protic
solvent that stabilizes the carbocation,
increasing the reaction rate, involving
retention and inversion as its
stereochemistry. SN1 reaction tends to favor
tertiary alkyl halides, viewed as tertiary >
secondary >> primary.
In the case of chlorobenzene, strong bond is
present making ionization to carbocation a
high energy process forming too unstable
product.
SN2
Alkyl halide and nucleophile was the basis
of kinetics for SN2 reaction, which requires
strong nucleophile, with polar, aprotic
solvent, giving inversion of stereochemistry.
SN2 reaction usually happens faster with
primary alkyl halides followed by secondary
alkyl halides, which is inversely related to
SN1 reaction.
In the case of chlorobenzene, aromatic ring
blocks nucleophile attack from behind
making inversion not possible.
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