For a lab, I had to react toulene with 1% I2 in dichloromethane. Would HI form as a result of this?

Logically, I think there would be no reaction because toulene looks too stable. But a colour change occured. Why would this happen?

Sorry, I meant hexane and not toulene.

For hexane, I would expect a reaction to occur, but the colour stayed dark purplish. Would HI form here?

If the color stayed dark purple, that would tell me no reaction occurred, or at least would give me a strong hint in that direction.

To determine whether HI would form as a result of the reaction between toluene and 1% I2 in dichloromethane, we need to consider the reactivity of the components involved.

Toluene (C7H8) is an aromatic compound, which makes it relatively stable due to the resonance in the benzene ring. On the other hand, iodine (I2) is a halogen with higher reactivity. Dichloromethane (CH2Cl2) is a nonpolar solvent commonly used in organic chemistry.

When toluene reacts with 1% I2 in dichloromethane, color changes can occur due to the formation of an intermediate species, typically referred to as the "iodonium ion" (R3I+), where R represents the organic moiety (in this case, the toluene). The iodonium ion is responsible for the color change since it absorbs light in the visible spectrum.

While the formation of the iodonium ion does not directly yield HI, it indicates that some reaction has occurred between toluene and iodine. The iodonium ion can further react with certain nucleophiles to generate a variety of products, such as protonated forms of the nucleophile, which might include HI. However, the specific details of the reaction and whether HI is indeed produced would depend on the experimental conditions and the concentrations of the reactants.

Therefore, the observed color change suggests that a reaction has taken place between toluene and iodine, leading to the formation of the iodonium ion. However, it does not necessarily imply the formation of HI without further details about the reaction conditions and the presence of other nucleophilic species. To confirm the presence of HI, additional analyses or tests, such as titrations or NMR spectroscopy, would be required.