HYDROCARBONS

In bromine tests, bromine does not react with saturated hydrocarbons (alkanes)
because alkanes contain only C-C bonds which cannot add bromine. Where in the
cycloalkanes solution, the color of the bromine solution was only diluted to orange
to light orange unless added with UV light where it resulted in Bromine slowly
disappearing over time. Bromine readily reacts with unsaturated hydrocarbons due
to the C=C bonds that can be broken through addition reaction. Where adding the
bromine solution to Cyclohexene will result in the disappearance of color of the
bromine solution after each drop and agitation. Aromatic Hydrocarbons are
unreactive with bromine without a catalyst and may result in the dilution of the
color of bromine to orange to yellow. In adding KMnO4 to cyclohexane, the KMnO4
was only diluted indicated that it is unreactive to alkanes. In adding KMnO4 to
cyclohexene, it resulted in forming a purple precipitate. Aromatic Hydrocarbons just
like with alkanes are unreactive to potassium permanganate.
12. Conclusion Hydrocarbons can be known and be differentiated by their physical
properties and chemical reactivity. According to their solubility, these hydrocarbons
are insoluble; immiscible to water as they are nonpolar substances as opposed to
the high polarity of water. The densities are the same for each with the exception
chlorobenzene due to the hydrogen bonds that have to be broken, the dispersion
forces that are acting upon the molecule as opposed to making new bonds in
reacting water with chlorobenzene. These hydrocarbons also react with a conc.
H2SO4 solution although insoluble forming hydrogen bonds to the hydrocarbons.
Even Aromatic compounds also react with conc. Sulfuric acid as it undergoes a
substitution reaction. Alkanes are unreactive to bromine unless under special
condition or catalyst like being exposed to UV light also alkanes are unreactive to
potassium permanganate. Alkenes are readily reactive to bromine since its double
bounds can be broken easily through addition reaction also is relatively similar if
alkenes are added with KMnO4. Aromatic Compounds are unreactive because they
are usually stable and can only be reacted if given a catalyst.
toluene + KMnO4 ===> benzoic acid
cyclohexene + KMnO4 ===> 1,2-cyclohexadiol

hexane + KMnO4 ===> no reaction

Addition of Bromine (Br2)

As mentioned above, saturated hydrocarbons will only react with bromine under free radical conditions,
meaning you have to add UV light. So simply adding some bromine to cyclohexane wont cause a reaction
to occur. Aromatic hydrocarbons can react with bromine only in the presence of a strong Lewis acid
catalyst such as FeBr3- youll learn about this next semester (Carey CH 12.5). So simply adding some
bromine to toluene wont cause a reaction to occur. Cyclohexene will readily react with bromine (see
Carey CH 6.15 and 6.16).

Reaction with Potassium

Permanganate (KMnO4)
Potassium permanganate reacts with anything
unsaturated. KMnO4 reacts with alkenes to
form vicinal diols (similar mechanism as with OsO 4, Carey CH 15.5). KMnO4 will also react with alkyl
benzenes, such as toluene, to form benzoic acids (Carey CH 11.13). Although I dont think any reaction will
take place without adding heat. Alkanes wont react with KMnO 4.

Reaction with Sulfuric Acid (H2SO4)

Sulfuric acid reacts with both alkenes and aromatic
hydrocarbons, although in different ways. Sulfuric acid adds to
cyclohexene via an acid catalyzed addition (Carey CH 6.9).
Sulfuric acid adds to toluene via electrophilic aromatic
substitution- once again, something youll learn about next
semester (Carey CH 12.4). Sulfuric acid wont react with
cyclohexane.