Free radical halogenation question

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In summary, the initiation step in chlorination of methane produces two chlorine radicals, which then participate in propagation steps with other molecules of methane until termination reactions occur.
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The initiation step in chlorination of methane is as follows...

http://upload.wikimedia.org/wikipedia/en/thumb/3/32/MethaneChlorinationMechanismInitiation.svg/260px-MethaneChlorinationMechanismInitiation.svg.png

We get two chlorine radicals as a result.

Next we have two propagation steps

http://upload.wikimedia.org/wikipedia/en/4/48/MethaneChlorinationPropagationStep.svg (won't let me embed the pic, sorry guys!)Ok, my understanding of this is... in the initiation step, the Cl2 was broken into two Cl radicals. ONE Cl radical moved on to the next step and reacted with the methyl group forming a methyl radical and HCl. THEN, the methyl radical reacted with Cl2 to form chloromethane and a chlorine radical.

My question is, Where does the SECOND Cl radical that was produced in the initiation step go? Because only ONE Cl radical reacted with the methyl group and then the methyl radical reacted with Cl2. In my mind, there is a Cl radical unaccounted for, but this is not explained in any example I can find (in a book or online)?

Thanks!
 
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It performs the same reaction with other molecules of methane. Eventually, you can get termination reactions that get rid of the radicals (often, this involves two radicals bonding together, e.g. Cl• + Cl• --> Cl2).
 
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I can understand your confusion about the second chlorine radical in the initiation step of chlorination of methane. However, it is important to note that the second chlorine radical is not unaccounted for. In fact, it is involved in the second propagation step, as shown in the second diagram you provided.

In the first propagation step, one chlorine radical reacts with the methyl group to form a methyl radical and HCl. This methyl radical then reacts with another chlorine molecule to form chloromethane and a second chlorine radical. This second chlorine radical then goes on to react with another methyl group, continuing the propagation process.

Therefore, both chlorine radicals produced in the initiation step are used in the propagation steps, and none are left unaccounted for. This is a crucial aspect of the free radical halogenation process, as it ensures that the reaction continues and multiple chlorination products are formed.

I hope this explanation helps to clarify your understanding of the process. If you have any further questions, please feel free to ask. it is important to always question and seek a deeper understanding of scientific concepts. Keep up the curiosity!
 

1. What is free radical halogenation?

Free radical halogenation is a chemical reaction in which a halogen (such as chlorine or bromine) is added to an alkane or alkene molecule to form a new halogenated compound. This reaction is initiated by the presence of a free radical, which is a highly reactive species with an unpaired electron.

2. What are the steps involved in free radical halogenation?

The first step is the initiation, where a free radical is formed through the homolytic cleavage of a halogen molecule by heat or light. The second step is the propagation, where the free radical reacts with an alkane or alkene molecule to form a new halogenated compound and generate a new free radical. The third and final step is termination, where two free radicals combine to form a stable molecule, effectively stopping the reaction.

3. What is the purpose of using a halogen in free radical halogenation?

The halogen serves as a catalyst in the reaction, meaning it helps to initiate and facilitate the reaction without being consumed in the process. Additionally, the halogen also adds a new functional group to the alkane or alkene, making it more reactive and potentially useful in other chemical reactions.

4. What are the factors that affect the rate of free radical halogenation?

The rate of free radical halogenation can be affected by the concentration of reactants, temperature, and the presence of any inhibitors or catalysts. Additionally, the type of halogen and the structure of the alkane or alkene can also impact the reaction rate.

5. What are some applications of free radical halogenation in industry?

Free radical halogenation is commonly used in the production of plastics, such as PVC and Teflon, as well as in the synthesis of pharmaceuticals and agrochemicals. It is also used in the purification of water and in the production of certain solvents and refrigerants.

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