When a mixture of methane and bromine is exposed to visible light, the following reaction occurs slowly: $$ \mathrm{CH}_{4}(g)+\mathrm{Br}_{2}(g) \longrightarrow \mathrm{CH}_{3} \mathrm{Br}(g)+\mathrm{HBr}(g) $$ Suggest a reasonable mechanism for this reaction. (Hint: Bromine vapor is deep red; methane is colorless.)

Short Answer

Expert verified
The reasonable mechanism for this reaction includes three steps: initiation, where bromine breaks down into two bromine radicals upon absorption of visible light; propagation, where the bromine radical and a methane molecule react to form a methyl radical and HBr, the methyl radical then reacts with another bromine molecule to form bromomethane and another bromine radical; termination, where two radicals combine to form a stable molecule.

Step by step solution

01

Proposing Step 1: Initiation

The reaction begins with an initiation step where the bromine molecule absorbs visible light and breaks down into two bromine radicals. This is represented by the equation: \[ \mathrm{Br}_{2}(g) \xrightarrow{\text{light}} 2\mathrm{Br \cdot }(g) \]
02

Proposing Step 2: Propagation

The bromine radical formed in the initiation step can now react with a methane molecule. A radical reaction between methane and a bromine radical occurs, forming a methyl radical and a molecule of hydrogen bromide. Also, the methyl radical can further react with a molecule of bromine to form bromomethane and another bromine radical. This radical can then cause another methane molecule to react, hence, this step is self-propagating. This is represented by the two equations: \[ \mathrm{CH}_{4}(g)+\mathrm{Br \cdot }(g) \rightarrow \mathrm{CH}_{3} \cdot (g)+\mathrm{HBr}(g) \] and \[ \mathrm{CH}_{3} \cdot (g)+\mathrm{Br}_{2}(g) \rightarrow \mathrm{CH}_{3} \mathrm{Br}(g)+\mathrm{Br \cdot }(g) \]
03

Proposing Step 3: Termination

The reaction ends with a termination step when two radicals react to form a stable molecule. Several reactions are possible, two radicals generated in the reactions can combine. In this case, the three possible termination steps are: \[ \mathrm{Br \cdot }(g) + \mathrm{Br \cdot }(g) \rightarrow \mathrm{Br}_{2}(g) \] or \[ \mathrm{CH}_{3} \cdot (g) + \mathrm{CH}_{3} \cdot (g) \rightarrow \mathrm{CH}_{3} - \mathrm{CH}_{3}(g)\] or \[ \mathrm{CH}_{3} \cdot (g) + \mathrm{Br \cdot }(g) \rightarrow \mathrm{CH}_{3} \mathrm{Br}(g) \]

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Radical Halogenation
Radical halogenation is a chemical reaction where a halogen atom is introduced into an organic molecule in the presence of sufficient energy, typically from heat or light. This process involves the creation of highly reactive species known as radicals, which then trigger a chain reaction that results in the halogenation of the organic compound.

In the context of the given exercise, where methane reacts with bromine under the influence of light, the color change mentioned (from deep red to colorless) is indicative of the bromine molecules reacting and being consumed. The bromine molecule dissociates into two bromine radicals, which are the key reactive intermediates that drive the reaction forward. As this process unfolds, various steps ensure the reaction's progression from reactants to products.
Initiation Step in Radical Reactions
The initiation step in radical reactions is where the first reactive intermediates are formed. It is essentially the 'starting gun' for the reaction. This step is crucial because it generates the radicals that will participate in further steps of the reaction.

For the exercise involving methane and bromine, the initiation occurs when the bromine molecule (\r\( \r\text{Br}_2 \r\)) absorbs visible light and splits into two bromine radicals (\r\( \r\text{Br} \r\text{•} \r\)). This is a homolytic cleavage, meaning that the electrons in the bromine-bromine bond are evenly divided between the two bromine atoms, each taking one electron and thereby forming two radicals.
Propagation Step in Radical Reactions
After initiation, the reaction enters the propagation step. This is where the bulk of the reaction occurs and the radicals generated in the initiation step react with stable molecules to form new radicals, perpetuating the chain reaction.

Within the methanol and bromine example, there are two propagation steps. The first is when a bromine radical reacts with methane (\r\( \r\text{CH}_4 \r\)), resulting in the formation of a methyl radical (\r\( \r\text{CH}_3 \r\text{•} \r\)) and hydrogen bromide (\r\( \r\text{HBr} \r\)). The newly formed methyl radical is highly reactive and doesn’t remain idle. It swiftly reacts with another bromine molecule (\r\( \r\text{Br}_2 \r\)), forming bromomethane (\r\( \r\text{CH}_3\text{Br} \r\)) and another bromine radical. This newly regenerated bromine radical can then react with another methane molecule, creating a cycle that continues to feed the reaction.
Termination Step in Radical Reactions
Finally, the termination step caps off the radical chain reaction. At this point, radical species combine to form stable, non-radical compounds, thus effectively halting the chain propagation. The combination of radicals happens as their concentration decreases and the likelihood of their encounter increases.

Several terminations are possible in the methane bromination example. Two bromine radicals can recombine to form a bromine molecule (\r\( \r\text{Br} \r\text{•} + \text{Br} \r\text{•} \rightarrow \text{Br}_2 \r\)). Alternatively, two methyl radicals can join to create ethane (\r\( \r\text{CH}_3 \r\text{•} + \text{CH}_3 \r\text{•} \rightarrow \text{CH}_3\text{CH}_3 \r\)). Another possibility is a methyl radical combining with a bromine radical to give bromomethane (\r\( \r\text{CH}_3 \r\text{•} + \text{Br} \r\text{•} \rightarrow \text{CH}_3\text{Br} \r\)). These termination reactions ensure that the radical species are depleted, thereby concluding the overall chemical process.

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Most popular questions from this chapter

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