Question

Should Toluene have reacted with Sulfuric Acid, KMnO4, and 2% Bromine? Reaction?

I performed these tests in the lab but got negative results for all three. I think I didn't shake them enough because the double bonds should've gone some addition reaction, right?

Answer 1

Toluene reacts with Sulfuric Acid, KMnO4, and 2% Bromine

Alkene + Br2 Alkyl dibromide
Note: No heat or ultraviolet light is required for this reaction. The orange/brown Br2 is
dissolved in dichloromethane. The reaction proceeds with a loss of bromine color, which is a
positive test for the presence of a double bond. This reaction occurs quickly.
Caution: Even in the concentrations used, bromine is highly toxic and can cause burns.
Saturated sodium Thiosulfate solution is provided to neutralize Br2 that has been spilled on skin.
Permanganate Oxidation: (Von Bayer test)
3 Alkene + 2 KMnO4 + 4 H2O 3 Glycol + 2 MnO2 + 2 KOH
Note: In the course of this reaction the purple color of the aqueous potassium
permanganate is replaced by solid brown manganese (IV) oxide (MnO2). The color change is a positive test for the presence of a double bond. Although this is a good test to differentiate
alkanes and aromatics from alkenes, other materials besides alkenes react with aqueous KMnO4.
Addition of Hydrogen Sulfate:
Alkene + H2SO4 Alkyl hydrogen sulfate
Note: Alkenes react with cold concentrated sulfuric acid and appear to go into solution. Alkanes and most aromatics do not react. Alkenes can also thicken or change color, which also indicates a reaction.