Experiment 11

Hydrocarbons

-Group 5
Objectives
To determine if the hydrocarbon is saturated or not through different
tests
To test the miscibility of organic compounds in water
Pre Laboratory Assignment
1. What precautionary measures should be taken in this experiment
-Sulfuric acids attacks skin and fabrics very swiftly. If you spill
some on yourself or others, rinse quickly with copious amounts of cold
water at once
-Never pour sulfuric acid directly into a sink. Pour waste sulfuric
acid into a large amount of cold water to dilute it then pour it directly
into the drain hole
-Bromine as pure liquid element can cause severe, painful burns.
Its vapors are very irritating to the nose and throat
-When preparing acetylene, no one is allowed to operate the
burner
Pre Laboratory Assignment
2. How would you account for the reaction of alkanes towards the
Bromine test?
Alkanes react slowly or not at all with bromine at room temperature in
the dark, but in the presence of sunlight or high temperature,
substitution:
R-H + Br2 --light--> R-Br + HBr
Pre Laboratory Assignment
3. Write the equations for the reaction in the presence of sunlight
a. methane and bromine in the presence of sunlight

b. calcium carbide and water

CaC2(s) + 2H2O(l)------> Ca(OH)2(s) + C2H2(g)
Results: Synthesis and reaction of acetylene

Reagent Observation
0.1% KMnO4 Initial color of the solution is violet. When acetylene
was bubbled through, the solution changed its color
to light purple -> clear liquid with brownish-red
precipitate
0.1% Bromine solution Initial color of the solution is golden yellow. When
acetylene was bubbled, the solution became light
yellow then changed to clear solution with white solid
settled at the bottom
Results: Other Tests
Test Hexane Cyclohexene toluene
Solubility in water Immiscible Immiscible Immiscible
Solubility in another + cyclohexene: miscible +toluene: miscible +hexane: miscible
hydrocarbon
H2SO4 No change of color Black precipitate formed No change of color
2 layers formed Solution turned black 2 layers formed
Test tube became hot
Bromine w/o light When bromine was Brownish-red color of No reaction
added the colorless bromine disappears after Brownish-red color of
solution turned to it was added bromine did not
brownish-red disappear after it was
added
Bromine w/light After 5 mins. Brownish
red color disappears
KMnO4 No reaction Violet solution turned No reaction
No change in color clear No change in color
Brown precipitate formed
Discussion: Synthesis and reaction of
acetylene
Calcium carbide reacts with water to form acetylene gas and calcium
hydroxide
Discussion: Solubility
All hydrocarbons that were tested are immiscible with water. Solubility
can be predicted with the rule of like dissolves like. Since
hydrocarbons are non polar while water is polar, mixing the two would
form two separate layers.

All hydrocarbons were miscible with each other since they are all non
polar
Discussion: Sulfuric Acid test
Alkenes react with concentrated sulfuric acid by addition.
Saturated hydrocarbons are unreactive (additions are not possible)
Aromatic compounds also are unreactive since addition reactions are
difficult.
Discussion: Bromine Test
The bromine test is used to determine if the organic compound
contains any C=C bonds
Bromine does not react with an alkane because the alkane contains
only C-C bonds which cannot add the bromine. It will only react with
an alkane through the use of UV light
Aromatic compounds resist addition reactions because of their
"aromaticity": the possession of a closed loop (sextet) of electrons.
These compounds react with bromine in the presence of a catalyst
such as iron filings or aluminum chloride.
Discussion: Baeyers Test
Potassium Permanganate does not react with alkanes because they
are saturated
When it is added to an alkene, the purple color slowly disappears and
a brown MnO2 precipitate forms. The appearance of brown
precipitate indicates a positive test for unsaturation
Aromatic compounds are generally unreactive because of their
stability