Physico-chemical Properties of Aliphatic and Aromatic

Activity Hydrocarbons, and Organic halides

No.4 Title of the Activity

Instructions:

1. Watch the video below and answer the questions:

a. https://www.youtube.com/watch?v=JlgP7DJKYVg
b. https://www.youtube.com/watch?v=ZXcS3oY9wQo
c. https://www.youtube.com/watch?v=wnk7ryf4TGc
d. https://www.youtube.com/watch?v=PgVLjWXlfj4
e. https://www.youtube.com/watch?v=o-Cl88fLixs
2. Complete the table by providing theoretical results.
3. All questions and answers should be typewritten. Font: Arial, size 12 and justified
paragraph.
4. Questions in black color and your answers in red color.
5. Submit as pdf file not later than 12 midnight of July 12, 2021.
6. FILE NAME should be: Act4_ph20_SURNAME

ALIPHATIC AND AROMATIC HYDROCARBONS

Procedure:

I. Physical State, Color, and Odor

1. Observe the physical state and appearance of the sample at room
temperature.
2. Note the color. With a wafting motion of the hand over the mouth of the
test tube, investigate the odor. Describe it.

II. Solubility in Conc. Sulfuric acid

1. Add a drop of the sample cautiously to about 1 mL of conc. Sulfuric acid.
Use dry and calibrated droppers. Describe its solubility as soluble
(miscible) or insoluble (immiscible).
2. Note any color change and/or warming effect.

III. Ignition Test

1. Place 3-5 drops of the liquid sample in a small evaporating dish and light
with a match. If the sample is solid, use a pinch amount.
2. Observe if the sample is flammable or not. Note the color of flame
produced. OPTIONAL: if flammable, observe burning time.
IV. Tests for Active Unsaturation
a. Baeyer’s Test
1. Place 5 drops of the sample in a dry test tube. Add 2 drops of 2%
KMnO4 solution. Shake the test tube vigorously and observe the
rate and extent at which the reagent is decolorized.
2. Note the formation of a brown suspension. Compare with water as
a negative control. Decolorization of the reagent is immediate if it
occurs within 1 minute. Note down the results.
b. Bromine Test
1. Place 5 drops of the sample in a dry test tube. Add 10 drops of
0.5% Br2 in CCl4 reagent. Shake the test tube vigorously and
observe the rate and extent (color change) by which the reagent
decolorized or when bromine color is discharged. OPTIONAL:
Place moistened blue litmus paper on a glass rod across the mouth
of the test tube and note any color change.
2. Compare with water as a negative control. of the reagent failed to
decolorize within 1 minute, expose the reaction mixture to sunlight.
Note down the results.

V. Tests for Aromaticity: Nitration

1. Place 2 mL of conc. Nitric acid in an Erlenmeyer flask. Immerse the
flask in an evaporating dish containing water and gradually add 2
mL of conc. Sulfuric acid. Cool the resulting mixture to room
temperature. This will serve as the nitrating mixture.
2. Place 5 drops of the sample in a dry test tube. Add 8 drops of the
nitrating mixture and shake the test tube to ensure complete
mixing. Note the formation of a yellow oily layer or droplet. Dilute
with 20 drops of water.
3. If there is no apparent reaction observed within minute, place the
test tube in a water bath (50degC) for 10 minutes. Dilute with 20
drops of water. Note down the results.

VI. Basic Oxidation

Place 4 drops of the sample in a test tube, add 8 drops of 2% KMnO 4

solution and 3 drops of 10% NaOH solution. Warm each tube in water bath 2
minutes and observe any color change and the formation of a brown precipitate.
Questions:

I. Hydrocarbons

Compound
Hexane Benzene
I. Physical state at Colorless Liquids Liquid
RT
Appearance Colorless Liquid Colorless Liquid
Color Colorless Colorless/ Light Yellow
Odor Petrolic Sweet Aromatic

II. Solubility in conc. Formation of a black layer Formation of a yellow green

H2SO4 layer
III. Ignition Test Luminous flame Luminous flame with soot
IV. Baeyer’s test No formation of brown No formation of brown
(theoretical visible suspension suspension
result)
Bromine Test No change No change
(theoretical visible
result)
V. Test For Formation of a clear oily Formation of a yellow oily
aromaticity layer layer
Nitration
(theoretical visible
result)
VI. Basic Oxidation No precipitate No precipitate
(theoretical visible
result)

1. Differentiate the following types of hydrocarbons based on structure:

a. Acyclic and cyclic

The two main types of compounds are acyclic and cyclic, which are distinguished
by the basic structure of the molecule. The difference between acyclic and cyclic
organic molecules is that acyclic compounds are linear, whereas cyclic
compounds are non-linear.
 b. Saturated, unsaturated, and actively unsaturated
Saturated and unsaturated hydrocarbons are distinguished by the
presence of only single covalent bonds between carbon atoms in the main
chain, whereas unsaturated hydrocarbons have at least one double or
triple covalent bond. Saturated and unsaturated hydrocarbons have
distinct properties as a result of these structural variations. A hydrocarbon
is saturated when it has only sigma bonds; however, it is actively
unsaturated when it contains both sigma and pi bonds.
c. Aliphatic and aromatic

Aliphatic and aromatic hydrocarbons are organic compounds made

completely of carbon and hydrogen atoms. The main difference between
aliphatic and aromatic hydrocarbons is that the carbon-to-hydrogen ratio of
aliphatic hydrocarbons is larger than that of aromatic hydrocarbons.

2. Give the reaction and general mechanism involved in the following chemical
tests:
a. Baeyer’s test
The loss of pink color can occur with or without the production of a brown
manganese oxide precipitate. When an alkaline potassium permanganate
is given to an unsaturated hydrocarbon in this test, the pink color of
potassium permanganate vanishes.
b. Bromine test
Alkenes react in the cold with pure liquid bromine, or with a solution of bromine in
an organic solvent like tetrachloromethane. The double bond breaks, and a
bromine atom becomes attached to each carbon. The bromine loses its original
red-brown color to give a colorless liquid. In the case of the reaction with ethene,
1,2-dibromoethane is formed. This decoloration of bromine is often used as a test
for a carbon-carbon double bond. If an aqueous solution of bromine is used
("bromine water"), you get a mixture of products. The other halogens, apart from
fluorine, behave similarly. (Fluorine reacts explosively with all hydrocarbons -
including alkenes - to give carbon and hydrogen fluoride.) If you are interested in
the reaction with, say, chlorine, all you have to do is to replace Br by Cl.

c. Aromaticity: nitration
3. How is Huckel’s rule applied in determining aromaticity?
In 1931, German chemist and physicist Erich Hückel proposed a theory to help
determine whether a planar ring molecule possesses aromatic characteristics.
According to his rule, a cyclic, planar molecule with 4n+2 electrons is aromatic.
This rule was given the moniker Hückel's Rule.
4. How does the number of carbon atoms affect the degree of luminosity of the
flame produced?
 According to the researches of this eminent chemist many very brilliant flames
exist in nature which cannot possibly contain any solid matter whatever. If, says
he, metallk arsenic be burned in oxygen gas it produces a most intense white
light. The vapor of sulphide of carbon burned in oxygen g-as or oxygen burned in
sulphide of carbon produces a light so intense that the eye can scarcely bear it,
and yet we are certain that no solid particles of matter are to be found here. The
temperature of ebullition of sulphur, 440 C. is much below that of the flame
produced in the above case. If protoxide of nitrogen be substituted for oxygen in
this experiment the result is identical; the light created possessing sufficient
intensity for the taking of instantaneous photographs or for producing the
phenomena of fluorescence.

ORGANIC HALIDES

Procedure:

I. Beilstein Test: Copper Halide Test

1. Make a small loop with one end of the copper wire. Heat the loop directly
in the oxidizing zone of a non-luminous flame. Continue heating until
green color imparted to the flame disappears.
2. Cool the loop slightly and dip it 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 blue-green (or green) –
colored indicates the presence of chloride, bromine, or iodine.

II. SN1 Reactivity: Reaction with Alcoholic AgNO3

1. Add 5 drops of the sample to 20 drops of 2% ethanolic AgNO 3. Shake and
record the time in seconds or minutes for a silver halide precipitate to
form. Describe the color of the precipitate.

III. SN2 Reactivity: Reaction with NaI in Acetone

1. 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 precipitate.

Questions:

Results
Compound Beilstein test Reaction with 2% Reaction with
ethanolic AgNO3 15% NaI in
anhydrous
acetone
n-butyl chloride Green Flame Turbid solution in 30 White precipitate
seconds in 10
seconds

sec-butyl chloride Green Flame Turbid solution in 25 Pale yellow

seconds precipitate in
15 seconds

tert-butyl chloride Green Flame White precipitate White crystals in

formed 15
in 20 seconds seconds

chlorobenzene Green Flame Turbid solution in 50 White precipitate

seconds in 15
seconds

1. Differentiate primary, secondary and tertiary alpha-carbon atoms in organic

halides. What is common in their alpha-carbon atoms?
Primary carbons include only one carbon atom, secondary carbons contain two
carbon atoms, and tertiary carbons contain three carbon atoms.
2. Give the principle and general reaction involved in Beilstein test.
The experiment is created by the reaction of chlorine with copper compounds in
high-temperature burner flames. These conditions induce excited, green-colored
copper atoms or ions to form, turning the normally colorless (or slightly blue)
flame vividly green.
3. Differentiate SN1 and SN2 reactivity of organic halides in terms of the following;
a. Number of molecules involved in the rate-determining step

To 20 drops of 2 percent ethanolic AgNO3, 5 drops of each sample (n-

butyl chloride, sec-butyl chloride, tert-butyl chloride, and
chlorobenzene) were added.

After shaking the test tube, the time it took for the silver halide
precipitate to form was recorded.

b. Strength of the nucleophile reagent

Nucleophiles attack the substrate, donating an electron pair to the new
bond, and replacing the leaving group (a substitution). Powerful
nucleophiles, especially those with negative charges, favor the SN2
mechanism. Weaker nucleophiles such as water or alcohols favor the
SN1 mechanism.
4. Which organic halide/s studied is/are; Explain your answer
a. Positive with Beilstein test
All organic halides namely nbutyl 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
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
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.

In the case of chlorobenzene, aromatic ring blocks nucleophile attack
from behind making inversion not possible.